From a9dae0a0ad7bf459b50d0b05b9bdd00231a1f513 Mon Sep 17 00:00:00 2001
From: Barret Schloerke <barret@posit.co>
Date: Wed, 7 May 2025 12:58:21 -0400
Subject: [PATCH 01/34] Ignore _dev folder

---
 .Rbuildignore | 1 +
 .gitignore    | 1 +
 2 files changed, 2 insertions(+)

diff --git a/.Rbuildignore b/.Rbuildignore
index af0ed86c..d36604f3 100644
--- a/.Rbuildignore
+++ b/.Rbuildignore
@@ -14,3 +14,4 @@ _cache/
 ^[\.]?air\.toml$
 ^\.vscode$
 ^data-raw$
+^_dev$
diff --git a/.gitignore b/.gitignore
index 0160fa21..b46d1001 100644
--- a/.gitignore
+++ b/.gitignore
@@ -8,3 +8,4 @@ docs
 inst/doc
 
 /.quarto/
+_dev/

From 8c0ccb9ff0de2deceddb6ca360764f29826ae370 Mon Sep 17 00:00:00 2001
From: Barret Schloerke <barret@posit.co>
Date: Thu, 15 May 2025 10:33:37 -0400
Subject: [PATCH 02/34] Init pass at contents_record / contents_replay

Need to remove with_chat and instead use as argument. Avoids temp global state state / clearly provides context
---
 DESCRIPTION                          |   3 +-
 NAMESPACE                            |   3 +
 R/content-replay.R                   | 386 +++++++++++++++++++++++++++
 R/tools-def.R                        |   1 +
 man/chat_cloudflare.Rd               |   1 +
 man/chat_huggingface.Rd              |   1 +
 man/contents_record.Rd               |  24 ++
 tests/testthat/test-content-replay.R | 124 +++++++++
 8 files changed, 542 insertions(+), 1 deletion(-)
 create mode 100644 R/content-replay.R
 create mode 100644 man/contents_record.Rd
 create mode 100644 tests/testthat/test-content-replay.R

diff --git a/DESCRIPTION b/DESCRIPTION
index 61aacd97..94439773 100644
--- a/DESCRIPTION
+++ b/DESCRIPTION
@@ -59,6 +59,7 @@ RoxygenNote: 7.3.2
 Collate:
     'utils-S7.R'
     'types.R'
+    'ellmer-package.R'
     'tools-def.R'
     'content.R'
     'provider.R'
@@ -69,9 +70,9 @@ Collate:
     'content-image.R'
     'content-pdf.R'
     'turns.R'
+    'content-replay.R'
     'content-tools.R'
     'deprecated.R'
-    'ellmer-package.R'
     'httr2.R'
     'import-standalone-obj-type.R'
     'import-standalone-purrr.R'
diff --git a/NAMESPACE b/NAMESPACE
index d241e54f..95774282 100644
--- a/NAMESPACE
+++ b/NAMESPACE
@@ -51,6 +51,9 @@ export(content_pdf_file)
 export(content_pdf_url)
 export(contents_html)
 export(contents_markdown)
+export(contents_record)
+export(contents_replay)
+export(contents_replay_s7)
 export(contents_text)
 export(create_tool_def)
 export(google_upload)
diff --git a/R/content-replay.R b/R/content-replay.R
new file mode 100644
index 00000000..794fde42
--- /dev/null
+++ b/R/content-replay.R
@@ -0,0 +1,386 @@
+#' @include utils-S7.R
+#' @include turns.R
+#' @include tools-def.R
+#' @include content.R
+
+NULL
+
+#' Save and restore content
+#'
+#' @description
+#' These generic functions can be use to convert [Turn] contents or [Content]
+#' objects into easily serializable representations.
+#'
+#' * `contents_replay()` will accept a basic object and return a corresponding
+#'   [Turn] or [Content] object.
+#' * `contents_record()` will accept a [Turn] or [Content] object and return a
+#'   basic object that can be easily serialized.
+#' @export
+contents_record <- new_generic("contents_record", "content")
+# #' @export
+# contents_record_prop_names <- new_generic(
+#   "contents_record_prop_names",
+#   "content"
+# )
+
+# contents_replay_impl <- new_generic(
+#   "contents_replay_impl",
+#   "type",
+#   function(state, type) {
+#     S7::S7_dispatch()
+#   }
+# )
+
+# method(contents_record, Turn) <- function(content) {
+#   list(
+#     version = 1,
+#     type = "turn",
+#     props = list(
+#       role = content@role,
+#       contents = contents_record(content@contents),
+#       tokens = content@tokens,
+#       completed = content@completed
+#     )
+#   )
+# }
+method(contents_record, S7::S7_object) <- function(content) {
+  prop_names <- S7::prop_names(content)
+  list(
+    version = 1,
+    class = class(content)[1],
+    props = setNames(
+      lapply(prop_names, function(prop_name) {
+        prop_value <- S7::prop(prop_name, object = content)
+        if (S7_inherits(prop_value)) {
+          contents_record(prop_value)
+        } else {
+          prop_value
+        }
+      }),
+      prop_names
+    )
+  )
+}
+method(contents_record, Turn) <- function(content) {
+  list(
+    version = 1,
+    class = class(content)[1],
+    props = list(
+      role = content@role,
+      contents = lapply(content@contents, contents_record),
+      json = content@json,
+      tokens = content@tokens,
+      completed = content@completed
+    )
+  )
+}
+
+#' @rdname contents_record
+#' @export
+contents_replay <- function(obj) {
+  # Find any reason to not believe `obj` is a recorded object.
+  # If not a recorded object, return it as is.
+  # If it is a recorded s7 object, dispatch on the discovered class.
+
+  if (!is.list(obj)) {
+    return(obj)
+    # cli::cli_abort(
+    #   "Expected a list, but got {.val {obj}}.",
+    #   call = caller_env()
+    # )
+  }
+  if (!all(c("version", "class", "props") %in% names(obj))) {
+    return(obj)
+    # cli::cli_abort(
+    #   "Expected a list with version, class, and props keys, but got {.val {obj}}.",
+    #   call = caller_env()
+    # )
+  }
+  class_value <- obj$class
+  if (!(is.character(class_value) && length(class_value) > 0)) {
+    return(obj)
+    # cli::cli_abort(
+    #   "class key must be a string. {.val {class_value}}.",
+    #   call = caller_env()
+    # )
+  }
+  pkg_cls <- strsplit(class_value[1], "::")[[1]]
+  if (length(pkg_cls) != 2) {
+    return(obj)
+    # cli::cli_abort(
+    #   "class key must be a string with a package name. {.val {class_value}}.",
+    #   call = caller_env()
+    # )
+  }
+  pkg_name <- pkg_cls[1]
+  cls_name <- pkg_cls[2]
+
+  cls <- rlang::pkg_env(pkg_name)[[cls_name]]
+
+  if (is.null(cls)) {
+    return(obj)
+    # cli::cli_abort(
+    #   "class key must be a valid class name. {.val {class_value}}.",
+    #   call = caller_env()
+    # )
+  }
+
+  if (!S7_inherits(cls)) {
+    return(obj)
+    # cli::cli_abort(
+    #   "class key must be a S7 class. {.val {class_value}}.",
+    #   call = caller_env()
+    # )
+  }
+
+  # Manually retrieve the handler for the class as we dispatch on the class itself,
+  # not on an instance
+  # An error will be thrown if a method is not found,
+  # however we have a fallback for the `S7::S7_object` (the root base class)
+  handler <- S7::method(contents_replay_s7, cls)
+  handler(cls, obj)
+}
+
+#' @rdname contents_record
+#' @export
+contents_replay_s7 <- new_generic(
+  "contents_replay_s7",
+  "cls",
+  function(cls, obj) {
+    S7::S7_dispatch()
+  }
+)
+
+
+method(contents_replay_s7, S7::S7_object) <- function(cls, obj) {
+  stopifnot(obj$version == 1)
+
+  obj_props <- lapply(obj$props, contents_replay)
+  ## While this should give prettier tracebacks, it doesn't work
+  # > cls_name <- rlang::sym(obj$class[1])
+  # > rlang::inject((!!cls_name)(!!!obj_props))
+  # Error in `ellmer::Turn`(role = "user", contents = list(), json = list(),  :
+  # could not find function "ellmer::Turn"
+
+  print(cls)
+
+  rlang::inject(cls(!!!obj_props))
+}
+
+with_chat_env <- list2env(list())
+with_chat_set <- function(chat) {
+  if (is.null(chat)) {
+    with_chat_env$chat <- NULL
+    return()
+  }
+  if (!inherits(chat, "Chat")) {
+    cli::cli_abort(
+      "Expected a Chat object, but got {.val {chat}}.",
+      call = caller_env()
+    )
+  }
+  with_chat_env$chat <- chat
+}
+with_chat_get <- function() {
+  chat <- with_chat_env$chat
+  if (is.null(chat)) {
+    cli::cli_abort(
+      "No Chat object found in the environment.",
+      call = caller_env()
+    )
+  }
+  chat
+}
+with_chat <- function(chat, code) {
+  with_chat_set(chat)
+  on.exit(with_chat_set(NULL), add = TRUE)
+  force(code)
+}
+
+method(contents_record, ToolDef) <- function(content) {
+  list(
+    version = 1,
+    class = class(content)[1],
+    props = list(
+      name = content@name
+      # description = content$description,
+      # arguments = content$arguments,
+      # annotations = content$annotations
+    )
+  )
+}
+method(contents_replay_s7, ToolDef) <- function(cls, obj) {
+  if (obj$version != 1) {
+    cli::cli_abort(
+      "Unsupported version {.val {obj$version}}.",
+      call = caller_env()
+    )
+  }
+  chat <- with_chat_get()
+  tools <- chat$get_tools()
+
+  tool <- tools[[obj$props$name]]
+  # Return matched tool or NULL
+  return(tool)
+}
+
+tool_rnorm <- tool(
+  stats::rnorm,
+  "Drawn numbers from a random normal distribution",
+  n = type_integer("The number of observations. Must be a positive integer."),
+  mean = type_number("The mean value of the distribution."),
+  sd = type_number(
+    "The standard deviation of the distribution. Must be a non-negative number."
+  )
+)
+
+# method(contents_replay_impl, "S7") <- function(state) {
+#   if (!is.list(state)) {
+#     cli::cli_abort(
+#       "Expected a list, but got {.val {state}}.",
+#       call = caller_env()
+#     )
+#   }
+
+#   contents <- lapply(prop_names, function(prop_name) {
+#     prop_value <- S7::prop(prop_name, object = content)
+#     contents_replay(prop_value)
+#   })
+#   contents <- unlist(contents, recursive = FALSE)
+#   contents <- contents[!sapply(contents, is.null)]
+#   contents <- contents[contents != ""]
+#   contents
+# }
+
+# contents_list_replay <- function(state) {
+# }
+
+# contents_record_old <- new_generic("contents_record_old", "content")
+# method(contents_record_old_prop_names, S7_object) <- function(content) {
+#   S7::prop_names(content)
+# }
+
+# method(contents_record_old, S7_object) <- function(content) {
+#   prop_names <- contents_record_old_prop_names(content)
+#   if (length(prop_names) == 0) {
+#     return(NULL)
+#   }
+#   props <- lapply(prop_names, function(prop_name) {
+#     prop_value <- S7::prop(prop_name, object = content)
+#     contents_record_old(prop_value)
+#   })
+#   props <- setNames(props, prop_names)
+#   list(
+#     version = 1,
+#     type = "s7",
+#     class = class(content),
+#     props = props
+#   )
+# }
+
+# method(contents_record_old, S7::class_list) <- function(content) {
+#   lapply(content, contents_record_old)
+# }
+# method(contents_record_old, S7::class_any) <- function(content) {
+#   content
+# }
+
+# contents_replay_s7_cls <- function(state) {
+#   if (is.null(state)) {
+#     return(NULL)
+#   }
+#   if (state$version != 1) {
+#     cli::cli_abort(
+#       "Unsupported version {.val {state$version}}.",
+#       call = caller_env()
+#     )
+#   }
+
+#   if (!identical(state$type, "s7")) {
+#     cli::cli_abort(
+#       "Unsupported type {.val {state$type}}.",
+#       call = caller_env()
+#     )
+#   }
+
+#   class_value <- state$class
+#   if (is.null(class_value)) {
+#     cli::cli_abort(
+#       "class key must be provided. {.val {class_value}}."
+#     )
+#   }
+#   if (!is.character(class_value)) {
+#     cli::cli_abort(
+#       "class key must be a string. {.val {class_value}}."
+#     )
+#   }
+#   if (length(class_value) == 0) {
+#     cli::cli_abort(
+#       "class key must be a single string. {.val {class_value}}."
+#     )
+#   }
+#   if (nchar(class_value[0]) == 0) {
+#     cli::cli_abort(
+#       "class key must be a non-empty string. {.val {class_value}}."
+#     )
+#   }
+
+#   s7_cls_info <- strsplit(class_value[0], "::")[[1]]
+#   s7_cls_pkg <- s7_cls_info[1]
+#   s7_cls_name <- s7_cls_info[2]
+#   s7_cls <- rlang::pkg_env(s7_cls_pkg)[[s7_cls_name]]
+
+#   contents_replay(s7_cls, state)
+#   # s7_cls
+# }
+
+# method(contents_replay, S7::class_list) <- function(state) {
+#   lapply(state, contents_replay)
+# }
+# method(contents_replay, S7::class_any) <- function(cls, state) {
+#   state
+# }
+
+# method(contents_replay, S7_object) <- function(state, type) {
+#   prop_names <- contents_record_prop_names(content)
+#   if (length(prop_names) == 0) {
+#     return(NULL)
+#   }
+
+#   props <- lapply(prop_names, function(prop_name) {
+#     prop_value <- S7::prop(prop_name, object = content)
+#     contents_replay(prop_value)
+#   })
+
+#   rlang::inject(cls(!!!state$props))
+# }
+
+# method(contents_replay, Turn) <- function(object) {
+#   if (object$version != 1) {
+#     cli::cli_abort(
+#       "Unsupported version {.val {object$version}}.",
+#       call = caller_env()
+#     )
+#   }
+#   if (object$type != "turn") {
+#     cli::cli_abort(
+#       "Unsupported type {.val {object$type}}.",
+#       call = caller_env()
+#     )
+#   }
+#   contents <- lapply(content@contents, contents_replay)
+#   contents <- unlist(contents, recursive = FALSE)
+#   contents <- contents[!sapply(contents, is.null)]
+#   contents <- contents[contents != ""]
+#   contents
+# }
+# method(contents_replay, S7_object) <- function(content) {
+#   contents <- lapply(prop_names, function(prop_name) {
+#     prop_value <- S7::prop(prop_name, object = content)
+#     contents_replay(prop_value)
+#   })
+#   contents <- unlist(contents, recursive = FALSE)
+#   contents <- contents[!sapply(contents, is.null)]
+#   contents <- contents[contents != ""]
+#   contents
+# }
diff --git a/R/tools-def.R b/R/tools-def.R
index 2257bea9..920af1c3 100644
--- a/R/tools-def.R
+++ b/R/tools-def.R
@@ -1,5 +1,6 @@
 #' @include utils-S7.R
 #' @include types.R
+#' @include ellmer-package.R
 NULL
 
 #' Define a tool
diff --git a/man/chat_cloudflare.Rd b/man/chat_cloudflare.Rd
index a177b77f..fe9ecee7 100644
--- a/man/chat_cloudflare.Rd
+++ b/man/chat_cloudflare.Rd
@@ -76,6 +76,7 @@ Other chatbots:
 \code{\link{chat_github}()},
 \code{\link{chat_google_gemini}()},
 \code{\link{chat_groq}()},
+\code{\link{chat_huggingface}()},
 \code{\link{chat_mistral}()},
 \code{\link{chat_ollama}()},
 \code{\link{chat_openai}()},
diff --git a/man/chat_huggingface.Rd b/man/chat_huggingface.Rd
index 592ca721..84db40c1 100644
--- a/man/chat_huggingface.Rd
+++ b/man/chat_huggingface.Rd
@@ -78,6 +78,7 @@ Other chatbots:
 \code{\link{chat_anthropic}()},
 \code{\link{chat_aws_bedrock}()},
 \code{\link{chat_azure_openai}()},
+\code{\link{chat_cloudflare}()},
 \code{\link{chat_cortex_analyst}()},
 \code{\link{chat_databricks}()},
 \code{\link{chat_deepseek}()},
diff --git a/man/contents_record.Rd b/man/contents_record.Rd
new file mode 100644
index 00000000..d43e157e
--- /dev/null
+++ b/man/contents_record.Rd
@@ -0,0 +1,24 @@
+% Generated by roxygen2: do not edit by hand
+% Please edit documentation in R/content-replay.R
+\name{contents_record}
+\alias{contents_record}
+\alias{contents_replay}
+\alias{contents_replay_s7}
+\title{Save and restore content}
+\usage{
+contents_record(content, ...)
+
+contents_replay(obj)
+
+contents_replay_s7(cls, obj)
+}
+\description{
+These generic functions can be use to convert \link{Turn} contents or \link{Content}
+objects into easily serializable representations.
+\itemize{
+\item \code{contents_replay()} will accept a basic object and return a corresponding
+\link{Turn} or \link{Content} object.
+\item \code{contents_record()} will accept a \link{Turn} or \link{Content} object and return a
+basic object that can be easily serialized.
+}
+}
diff --git a/tests/testthat/test-content-replay.R b/tests/testthat/test-content-replay.R
new file mode 100644
index 00000000..8c357f97
--- /dev/null
+++ b/tests/testthat/test-content-replay.R
@@ -0,0 +1,124 @@
+tool_rnorm <- tool(
+  stats::rnorm,
+  "Drawn numbers from a random normal distribution",
+  n = type_integer("The number of observations. Must be a positive integer."),
+  mean = type_number("The mean value of the distribution."),
+  sd = type_number(
+    "The standard deviation of the distribution. Must be a non-negative number."
+  )
+)
+
+chat <- chat_ollama(model = "llama3.2")
+chat$register_tool(tool_rnorm)
+
+
+expect_record_replay <- function(x) {
+  # Simulate the full bookmarking experience:
+  # * Record the object to something serializable
+  # * Serialize the object to JSON via shiny; "bookmark"
+  # * Unserialize the object from JSON via shiny; "restore"
+  # * Replay the unserialized object to the original object
+  # * Check that the replayed object has the same class as the original object
+  # * Check that the replayed object has the same properties as the original object
+  # expect_silent({
+  obj <- contents_record(x)
+
+  # Bbookmark
+  serialized <- shiny:::toJSON(obj)
+  unserialized <- shiny:::safeFromJSON(serialized)
+
+  replayed <- contents_replay(unserialized)
+  # })
+
+  expect_s3_class(replayed, class(x)[1])
+  expect_equal(S7::props(replayed), S7::props(x))
+}
+
+# -------------------------------------------------------------------------
+
+test_that("can round trip of Content record/replay", {
+  expect_record_replay(Content())
+})
+
+test_that("can round trip of ContentText record/replay", {
+  expect_record_replay(ContentText("hello world"))
+})
+
+test_that("can round trip of ContentImageInline record/replay", {
+  expect_record_replay(
+    ContentImageInline("image/png", "abcd123")
+  )
+})
+
+test_that("can round trip of ContentImageRemote record/replay", {
+  expect_record_replay(
+    ContentImageRemote("https://example.com/image.jpg", detail = "")
+  )
+})
+
+test_that("can round trip of ContentJson record/replay", {
+  expect_record_replay(
+    ContentJson(list(a = 1:2, b = "apple"))
+  )
+})
+
+test_that("can round trip of ContentSql record/replay", {
+  expect_record_replay(
+    ContentSql("SELECT * FROM mtcars")
+  )
+})
+
+test_that("can round trip of ContentSuggestions record/replay", {
+  expect_record_replay(
+    ContentSuggestions(
+      c(
+        "What is the total quantity sold for each product last quarter?",
+        "What is the average discount percentage for orders from the United States?",
+        "What is the average price of products in the 'electronics' category?"
+      )
+    )
+  )
+})
+
+test_that("can round trip of ContentThinking record/replay", {
+  expect_record_replay(
+    ContentThinking("A **thought**.")
+  )
+})
+
+test_that("can round trip of ContentTool record/replay", {
+  # TODO: barret - test tooldef, need to adjust replay to accept client to recontruct tooldef
+  expect_record_replay(
+    ContentToolRequest("ID", "tool_name", list(a = 1:2, b = "apple"))
+  )
+
+  with_chat(chat, {
+  })
+})
+
+test_that("can round trip of ToolDef record/replay", {
+  with_chat(chat, {
+    expect_record_replay(tool_rnorm)
+  })
+})
+
+test_that("can round trip of ContentToolResult record/replay", {
+  expect_record_replay(
+    ContentToolResult(
+      value = "VALUE",
+      error = NULL,
+      extra = list(extra = 1:2, b = "apple"),
+      request = NULL
+    )
+  )
+  # TODO: Barret test real error value
+  # TODO: Barret test with request object
+})
+
+test_that("can round trip of ContentUploaded record/replay", {
+  expect_record_replay(ContentUploaded("https://example.com/image.jpg"))
+})
+
+test_that("can round trip of ContentPDF record/replay", {
+  expect_record_replay(ContentPDF(type = "TYPE", data = "DATA"))
+})

From 60e9a706eb6b741c1ae817496eddd7461342c9a3 Mon Sep 17 00:00:00 2001
From: Barret Schloerke <barret@posit.co>
Date: Thu, 15 May 2025 10:48:51 -0400
Subject: [PATCH 03/34] Drop chat state during serialization / unserialization.
 Instead, pass chat throughout

---
 R/content-replay.R                   | 96 ++++++++++++++++------------
 man/contents_record.Rd               |  6 +-
 tests/testthat/test-content-replay.R | 58 ++++++++++-------
 3 files changed, 93 insertions(+), 67 deletions(-)

diff --git a/R/content-replay.R b/R/content-replay.R
index 794fde42..5469886a 100644
--- a/R/content-replay.R
+++ b/R/content-replay.R
@@ -16,7 +16,13 @@ NULL
 #' * `contents_record()` will accept a [Turn] or [Content] object and return a
 #'   basic object that can be easily serialized.
 #' @export
-contents_record <- new_generic("contents_record", "content")
+contents_record <- new_generic(
+  "contents_record",
+  "content",
+  function(content, ..., chat) {
+    S7::S7_dispatch()
+  }
+)
 # #' @export
 # contents_record_prop_names <- new_generic(
 #   "contents_record_prop_names",
@@ -43,7 +49,7 @@ contents_record <- new_generic("contents_record", "content")
 #     )
 #   )
 # }
-method(contents_record, S7::S7_object) <- function(content) {
+method(contents_record, S7::S7_object) <- function(content, ..., chat) {
   prop_names <- S7::prop_names(content)
   list(
     version = 1,
@@ -52,7 +58,7 @@ method(contents_record, S7::S7_object) <- function(content) {
       lapply(prop_names, function(prop_name) {
         prop_value <- S7::prop(prop_name, object = content)
         if (S7_inherits(prop_value)) {
-          contents_record(prop_value)
+          contents_record(prop_value, chat = chat)
         } else {
           prop_value
         }
@@ -61,13 +67,13 @@ method(contents_record, S7::S7_object) <- function(content) {
     )
   )
 }
-method(contents_record, Turn) <- function(content) {
+method(contents_record, Turn) <- function(content, ..., chat) {
   list(
     version = 1,
     class = class(content)[1],
     props = list(
       role = content@role,
-      contents = lapply(content@contents, contents_record),
+      contents = lapply(content@contents, contents_record, chat = chat),
       json = content@json,
       tokens = content@tokens,
       completed = content@completed
@@ -77,7 +83,14 @@ method(contents_record, Turn) <- function(content) {
 
 #' @rdname contents_record
 #' @export
-contents_replay <- function(obj) {
+contents_replay <- function(obj, ..., chat) {
+  if (!(R6::is.R6(chat) && inherits(chat, "Chat"))) {
+    cli::cli_abort(
+      "Expected a Chat object at `chat=`, but received {.val {chat}}.",
+      call = caller_env()
+    )
+  }
+
   # Find any reason to not believe `obj` is a recorded object.
   # If not a recorded object, return it as is.
   # If it is a recorded s7 object, dispatch on the discovered class.
@@ -138,7 +151,7 @@ contents_replay <- function(obj) {
   # An error will be thrown if a method is not found,
   # however we have a fallback for the `S7::S7_object` (the root base class)
   handler <- S7::method(contents_replay_s7, cls)
-  handler(cls, obj)
+  handler(cls, obj, chat = chat)
 }
 
 #' @rdname contents_record
@@ -146,16 +159,16 @@ contents_replay <- function(obj) {
 contents_replay_s7 <- new_generic(
   "contents_replay_s7",
   "cls",
-  function(cls, obj) {
+  function(cls, obj, ..., chat) {
     S7::S7_dispatch()
   }
 )
 
 
-method(contents_replay_s7, S7::S7_object) <- function(cls, obj) {
+method(contents_replay_s7, S7::S7_object) <- function(cls, obj, ..., chat) {
   stopifnot(obj$version == 1)
 
-  obj_props <- lapply(obj$props, contents_replay)
+  obj_props <- lapply(obj$props, contents_replay, chat = chat)
   ## While this should give prettier tracebacks, it doesn't work
   # > cls_name <- rlang::sym(obj$class[1])
   # > rlang::inject((!!cls_name)(!!!obj_props))
@@ -167,37 +180,37 @@ method(contents_replay_s7, S7::S7_object) <- function(cls, obj) {
   rlang::inject(cls(!!!obj_props))
 }
 
-with_chat_env <- list2env(list())
-with_chat_set <- function(chat) {
-  if (is.null(chat)) {
-    with_chat_env$chat <- NULL
-    return()
-  }
-  if (!inherits(chat, "Chat")) {
-    cli::cli_abort(
-      "Expected a Chat object, but got {.val {chat}}.",
-      call = caller_env()
-    )
-  }
-  with_chat_env$chat <- chat
-}
-with_chat_get <- function() {
-  chat <- with_chat_env$chat
-  if (is.null(chat)) {
-    cli::cli_abort(
-      "No Chat object found in the environment.",
-      call = caller_env()
-    )
-  }
-  chat
-}
-with_chat <- function(chat, code) {
-  with_chat_set(chat)
-  on.exit(with_chat_set(NULL), add = TRUE)
-  force(code)
-}
+# with_chat_env <- list2env(list())
+# with_chat_set <- function(chat) {
+#   if (is.null(chat)) {
+#     with_chat_env$chat <- NULL
+#     return()
+#   }
+#   if (!inherits(chat, "Chat")) {
+#     cli::cli_abort(
+#       "Expected a Chat object, but got {.val {chat}}.",
+#       call = caller_env()
+#     )
+#   }
+#   with_chat_env$chat <- chat
+# }
+# with_chat_get <- function() {
+#   chat <- with_chat_env$chat
+#   if (is.null(chat)) {
+#     cli::cli_abort(
+#       "No Chat object found in the environment.",
+#       call = caller_env()
+#     )
+#   }
+#   chat
+# }
+# with_chat <- function(chat, code) {
+#   with_chat_set(chat)
+#   on.exit(with_chat_set(NULL), add = TRUE)
+#   force(code)
+# }
 
-method(contents_record, ToolDef) <- function(content) {
+method(contents_record, ToolDef) <- function(content, ..., chat) {
   list(
     version = 1,
     class = class(content)[1],
@@ -209,14 +222,13 @@ method(contents_record, ToolDef) <- function(content) {
     )
   )
 }
-method(contents_replay_s7, ToolDef) <- function(cls, obj) {
+method(contents_replay_s7, ToolDef) <- function(cls, obj, ..., chat) {
   if (obj$version != 1) {
     cli::cli_abort(
       "Unsupported version {.val {obj$version}}.",
       call = caller_env()
     )
   }
-  chat <- with_chat_get()
   tools <- chat$get_tools()
 
   tool <- tools[[obj$props$name]]
diff --git a/man/contents_record.Rd b/man/contents_record.Rd
index d43e157e..b9015793 100644
--- a/man/contents_record.Rd
+++ b/man/contents_record.Rd
@@ -6,11 +6,11 @@
 \alias{contents_replay_s7}
 \title{Save and restore content}
 \usage{
-contents_record(content, ...)
+contents_record(content, ..., chat)
 
-contents_replay(obj)
+contents_replay(obj, ..., chat)
 
-contents_replay_s7(cls, obj)
+contents_replay_s7(cls, obj, ..., chat)
 }
 \description{
 These generic functions can be use to convert \link{Turn} contents or \link{Content}
diff --git a/tests/testthat/test-content-replay.R b/tests/testthat/test-content-replay.R
index 8c357f97..06d922b3 100644
--- a/tests/testthat/test-content-replay.R
+++ b/tests/testthat/test-content-replay.R
@@ -1,18 +1,10 @@
-tool_rnorm <- tool(
-  stats::rnorm,
-  "Drawn numbers from a random normal distribution",
-  n = type_integer("The number of observations. Must be a positive integer."),
-  mean = type_number("The mean value of the distribution."),
-  sd = type_number(
-    "The standard deviation of the distribution. Must be a non-negative number."
-  )
-)
-
-chat <- chat_ollama(model = "llama3.2")
-chat$register_tool(tool_rnorm)
+expect_record_replay <- function(
+  x,
+  ...,
+  chat = chat_ollama_test("Be as terse as possible; no punctuation")
+) {
+  rlang::check_dots_empty()
 
-
-expect_record_replay <- function(x) {
   # Simulate the full bookmarking experience:
   # * Record the object to something serializable
   # * Serialize the object to JSON via shiny; "bookmark"
@@ -20,14 +12,15 @@ expect_record_replay <- function(x) {
   # * Replay the unserialized object to the original object
   # * Check that the replayed object has the same class as the original object
   # * Check that the replayed object has the same properties as the original object
+
   # expect_silent({
-  obj <- contents_record(x)
+  obj <- contents_record(x, chat = chat)
 
   # Bbookmark
   serialized <- shiny:::toJSON(obj)
   unserialized <- shiny:::safeFromJSON(serialized)
 
-  replayed <- contents_replay(unserialized)
+  replayed <- contents_replay(unserialized, chat = chat)
   # })
 
   expect_s3_class(replayed, class(x)[1])
@@ -91,15 +84,36 @@ test_that("can round trip of ContentTool record/replay", {
   expect_record_replay(
     ContentToolRequest("ID", "tool_name", list(a = 1:2, b = "apple"))
   )
-
-  with_chat(chat, {
-  })
 })
 
 test_that("can round trip of ToolDef record/replay", {
-  with_chat(chat, {
-    expect_record_replay(tool_rnorm)
-  })
+  chat <- chat_ollama_test("Be as terse as possible; no punctuation")
+  tool_rnorm <- tool(
+    stats::rnorm,
+    "Drawn numbers from a random normal distribution",
+    n = type_integer("The number of observations. Must be a positive integer."),
+    mean = type_number("The mean value of the distribution."),
+    sd = type_number(
+      "The standard deviation of the distribution. Must be a non-negative number."
+    )
+  )
+  chat$register_tool(tool_rnorm)
+
+  # with_chat(chat, {
+  expect_record_replay(tool_rnorm, chat = chat)
+  # })
+
+  # with_chat(chat, {
+  expect_record_replay(
+    ContentToolRequest(
+      "ID",
+      "tool_name",
+      list(a = 1:2, b = "apple"),
+      tool = tool_rnorm
+    ),
+    chat = chat
+  )
+  # })
 })
 
 test_that("can round trip of ContentToolResult record/replay", {

From 17d41ebe18dda4911a67f582385f344ad847e7ea Mon Sep 17 00:00:00 2001
From: Barret Schloerke <barret@posit.co>
Date: Thu, 15 May 2025 15:18:52 -0400
Subject: [PATCH 04/34] Relocate expect_record_replay

---
 R/content-replay.R                   | 36 ++++++++++++++++++++++++++++
 tests/testthat/test-content-replay.R | 29 ----------------------
 2 files changed, 36 insertions(+), 29 deletions(-)

diff --git a/R/content-replay.R b/R/content-replay.R
index 5469886a..8dc9074c 100644
--- a/R/content-replay.R
+++ b/R/content-replay.R
@@ -396,3 +396,39 @@ tool_rnorm <- tool(
 #   contents <- contents[contents != ""]
 #   contents
 # }
+
+expect_record_replay <- function(
+  x,
+  ...,
+  chat = chat_ollama_test("Be as terse as possible; no punctuation")
+) {
+  rlang::check_dots_empty()
+
+  # Simulate the full bookmarking experience:
+  # * Record the object to something serializable
+  # * Serialize the object to JSON via shiny; "bookmark"
+  # * Unserialize the object from JSON via shiny; "restore"
+  # * Replay the unserialized object to the original object
+  # * Check that the replayed object has the same class as the original object
+  # * Check that the replayed object has the same properties as the original object
+
+  obj <- contents_record(x, chat = chat)
+
+  # obj_packed <- jsonlite:::pack(obj)
+
+  # Work around Shiny's terrible JSON serialization
+  # Use `as.character()` to remove the JSON class so that it is double serialized :-/
+  marshalled = as.character(jsonlite::serializeJSON(obj))
+
+  # Bookmark
+  serialized <- shiny:::toJSON(marshalled)
+  unserialized <- shiny:::safeFromJSON(serialized)
+
+  # obj_unpacked <- jsonlite:::unpack(unserialized)
+  unmarshalled <- jsonlite::unserializeJSON(unserialized)
+
+  replayed <- contents_replay(unmarshalled, chat = chat)
+
+  expect_s3_class(replayed, class(x)[1])
+  expect_equal(S7::props(replayed), S7::props(x))
+}
diff --git a/tests/testthat/test-content-replay.R b/tests/testthat/test-content-replay.R
index 06d922b3..1087a076 100644
--- a/tests/testthat/test-content-replay.R
+++ b/tests/testthat/test-content-replay.R
@@ -1,32 +1,3 @@
-expect_record_replay <- function(
-  x,
-  ...,
-  chat = chat_ollama_test("Be as terse as possible; no punctuation")
-) {
-  rlang::check_dots_empty()
-
-  # Simulate the full bookmarking experience:
-  # * Record the object to something serializable
-  # * Serialize the object to JSON via shiny; "bookmark"
-  # * Unserialize the object from JSON via shiny; "restore"
-  # * Replay the unserialized object to the original object
-  # * Check that the replayed object has the same class as the original object
-  # * Check that the replayed object has the same properties as the original object
-
-  # expect_silent({
-  obj <- contents_record(x, chat = chat)
-
-  # Bbookmark
-  serialized <- shiny:::toJSON(obj)
-  unserialized <- shiny:::safeFromJSON(serialized)
-
-  replayed <- contents_replay(unserialized, chat = chat)
-  # })
-
-  expect_s3_class(replayed, class(x)[1])
-  expect_equal(S7::props(replayed), S7::props(x))
-}
-
 # -------------------------------------------------------------------------
 
 test_that("can round trip of Content record/replay", {

From 8a3905d1a513c8dddd0922a2a80371fb2b5a5fef Mon Sep 17 00:00:00 2001
From: Barret Schloerke <barret@posit.co>
Date: Thu, 15 May 2025 15:19:09 -0400
Subject: [PATCH 05/34] Test with registered tool

---
 tests/testthat/test-content-replay.R | 27 +++++++++++++++++++++++++++
 1 file changed, 27 insertions(+)

diff --git a/tests/testthat/test-content-replay.R b/tests/testthat/test-content-replay.R
index 1087a076..eef34e8f 100644
--- a/tests/testthat/test-content-replay.R
+++ b/tests/testthat/test-content-replay.R
@@ -96,6 +96,33 @@ test_that("can round trip of ContentToolResult record/replay", {
       request = NULL
     )
   )
+
+  chat <- chat_ollama_test("Be as terse as possible; no punctuation")
+  tool_rnorm <- tool(
+    stats::rnorm,
+    "Drawn numbers from a random normal distribution",
+    n = type_integer("The number of observations. Must be a positive integer."),
+    mean = type_number("The mean value of the distribution."),
+    sd = type_number(
+      "The standard deviation of the distribution. Must be a non-negative number."
+    )
+  )
+  chat$register_tool(tool_rnorm)
+
+  expect_record_replay(
+    ContentToolResult(
+      value = "VALUE",
+      error = try(stop("boom"), silent = TRUE),
+      extra = list(extra = 1:2, b = "apple"),
+      request = ContentToolRequest(
+        "ID",
+        "tool_name",
+        list(a = 1:2, b = "apple"),
+        tool = tool_rnorm
+      )
+    ),
+    chat = chat
+  )
   # TODO: Barret test real error value
   # TODO: Barret test with request object
 })

From 540ff71970dda1eb4c63a0dd288ea676458c6b01 Mon Sep 17 00:00:00 2001
From: Barret Schloerke <barret@posit.co>
Date: Thu, 15 May 2025 15:20:10 -0400
Subject: [PATCH 06/34] Store more information in a ToolDef record. On restore,
 make a new ToolDef if one does not exist

---
 R/content-replay.R | 39 ++++++++++++++++++++++++++++-----------
 1 file changed, 28 insertions(+), 11 deletions(-)

diff --git a/R/content-replay.R b/R/content-replay.R
index 8dc9074c..b68f0b25 100644
--- a/R/content-replay.R
+++ b/R/content-replay.R
@@ -76,7 +76,8 @@ method(contents_record, Turn) <- function(content, ..., chat) {
       contents = lapply(content@contents, contents_record, chat = chat),
       json = content@json,
       tokens = content@tokens,
-      completed = content@completed
+      completed = content@completed,
+      # text = getter only!
     )
   )
 }
@@ -175,8 +176,6 @@ method(contents_replay_s7, S7::S7_object) <- function(cls, obj, ..., chat) {
   # Error in `ellmer::Turn`(role = "user", contents = list(), json = list(),  :
   # could not find function "ellmer::Turn"
 
-  print(cls)
-
   rlang::inject(cls(!!!obj_props))
 }
 
@@ -215,10 +214,15 @@ method(contents_record, ToolDef) <- function(content, ..., chat) {
     version = 1,
     class = class(content)[1],
     props = list(
-      name = content@name
-      # description = content$description,
-      # arguments = content$arguments,
-      # annotations = content$annotations
+      name = content@name,
+      # Do not record the function!
+      # It is not serializable and will not be neeeded after replay as the _real_ tool would be leveraged.
+      # However, keep all the other properties as the metadata could be useful.
+      fun = NULL,
+      description = content@description,
+      arguments = content@arguments,
+      convert = content@convert,
+      annotations = content@annotations
     )
   )
 }
@@ -229,16 +233,29 @@ method(contents_replay_s7, ToolDef) <- function(cls, obj, ..., chat) {
       call = caller_env()
     )
   }
+
   tools <- chat$get_tools()
+  matched_tool <- tools[[obj$props$name]]
 
-  tool <- tools[[obj$props$name]]
-  # Return matched tool or NULL
-  return(tool)
+  if (!is.null(matched_tool)) {
+    matched_tool
+  }
+
+  # If no tool is found, return placeholder tool
+  ToolDef(
+    name = obj$props$name,
+    # fun = NULL, # fun was not serialized
+    description = obj$props$description,
+    # TODO: Barret fix this
+    arguments = contents_replay(obj$props$arguments, chat = chat),
+    convert = obj$props$convert,
+    annotations = obj$props$annotations
+  )
 }
 
 tool_rnorm <- tool(
   stats::rnorm,
-  "Drawn numbers from a random normal distribution",
+  .description = "Drawn numbers from a random normal distribution",
   n = type_integer("The number of observations. Must be a positive integer."),
   mean = type_number("The mean value of the distribution."),
   sd = type_number(

From f423c076c70b9a3128e46cf2d9a492beda26377e Mon Sep 17 00:00:00 2001
From: Barret Schloerke <barret@posit.co>
Date: Thu, 15 May 2025 15:20:20 -0400
Subject: [PATCH 07/34] document

---
 NAMESPACE           | 2 +-
 man/chat_portkey.Rd | 6 +++---
 2 files changed, 4 insertions(+), 4 deletions(-)

diff --git a/NAMESPACE b/NAMESPACE
index 41dc2837..5cd0ed1f 100644
--- a/NAMESPACE
+++ b/NAMESPACE
@@ -64,13 +64,13 @@ export(interpolate_file)
 export(interpolate_package)
 export(live_browser)
 export(live_console)
-export(models_portkey)
 export(models_anthropic)
 export(models_aws_bedrock)
 export(models_google_gemini)
 export(models_google_vertex)
 export(models_ollama)
 export(models_openai)
+export(models_portkey)
 export(models_vllm)
 export(parallel_chat)
 export(parallel_chat_structured)
diff --git a/man/chat_portkey.Rd b/man/chat_portkey.Rd
index 159b72ab..1904fd72 100644
--- a/man/chat_portkey.Rd
+++ b/man/chat_portkey.Rd
@@ -32,9 +32,9 @@ models_portkey(
 \item{virtual_key}{A virtual identifier storing LLM provider's API key. See
 \href{https://portkey.ai/docs/product/ai-gateway/virtual-keys}{documentation}.}
 
-\item{model}{The model to use for the chat. The default, \code{NULL}, will pick
-a reasonable default, and tell you about. We strongly recommend explicitly
-choosing a model for all but the most casual use.}
+\item{model}{The model to use for the chat (defaults to "gpt-4o").
+We regularly update the default, so we strongly recommend explicitly specifying a model for anything other than casual use.
+Use \code{models_openai()} to see all options.}
 
 \item{params}{Common model parameters, usually created by \code{\link[=params]{params()}}.}
 

From 36544607008a24fbcbe4016409711ff37f712a32 Mon Sep 17 00:00:00 2001
From: Barret Schloerke <barret@posit.co>
Date: Mon, 19 May 2025 15:48:04 -0400
Subject: [PATCH 08/34] Remove commented code

---
 R/content-replay.R | 231 +--------------------------------------------
 1 file changed, 2 insertions(+), 229 deletions(-)

diff --git a/R/content-replay.R b/R/content-replay.R
index b68f0b25..4b5786e0 100644
--- a/R/content-replay.R
+++ b/R/content-replay.R
@@ -23,32 +23,6 @@ contents_record <- new_generic(
     S7::S7_dispatch()
   }
 )
-# #' @export
-# contents_record_prop_names <- new_generic(
-#   "contents_record_prop_names",
-#   "content"
-# )
-
-# contents_replay_impl <- new_generic(
-#   "contents_replay_impl",
-#   "type",
-#   function(state, type) {
-#     S7::S7_dispatch()
-#   }
-# )
-
-# method(contents_record, Turn) <- function(content) {
-#   list(
-#     version = 1,
-#     type = "turn",
-#     props = list(
-#       role = content@role,
-#       contents = contents_record(content@contents),
-#       tokens = content@tokens,
-#       completed = content@completed
-#     )
-#   )
-# }
 method(contents_record, S7::S7_object) <- function(content, ..., chat) {
   prop_names <- S7::prop_names(content)
   list(
@@ -98,33 +72,19 @@ contents_replay <- function(obj, ..., chat) {
 
   if (!is.list(obj)) {
     return(obj)
-    # cli::cli_abort(
-    #   "Expected a list, but got {.val {obj}}.",
-    #   call = caller_env()
-    # )
   }
   if (!all(c("version", "class", "props") %in% names(obj))) {
     return(obj)
-    # cli::cli_abort(
-    #   "Expected a list with version, class, and props keys, but got {.val {obj}}.",
-    #   call = caller_env()
-    # )
   }
+
   class_value <- obj$class
   if (!(is.character(class_value) && length(class_value) > 0)) {
     return(obj)
-    # cli::cli_abort(
-    #   "class key must be a string. {.val {class_value}}.",
-    #   call = caller_env()
-    # )
   }
+
   pkg_cls <- strsplit(class_value[1], "::")[[1]]
   if (length(pkg_cls) != 2) {
     return(obj)
-    # cli::cli_abort(
-    #   "class key must be a string with a package name. {.val {class_value}}.",
-    #   call = caller_env()
-    # )
   }
   pkg_name <- pkg_cls[1]
   cls_name <- pkg_cls[2]
@@ -133,18 +93,10 @@ contents_replay <- function(obj, ..., chat) {
 
   if (is.null(cls)) {
     return(obj)
-    # cli::cli_abort(
-    #   "class key must be a valid class name. {.val {class_value}}.",
-    #   call = caller_env()
-    # )
   }
 
   if (!S7_inherits(cls)) {
     return(obj)
-    # cli::cli_abort(
-    #   "class key must be a S7 class. {.val {class_value}}.",
-    #   call = caller_env()
-    # )
   }
 
   # Manually retrieve the handler for the class as we dispatch on the class itself,
@@ -179,35 +131,6 @@ method(contents_replay_s7, S7::S7_object) <- function(cls, obj, ..., chat) {
   rlang::inject(cls(!!!obj_props))
 }
 
-# with_chat_env <- list2env(list())
-# with_chat_set <- function(chat) {
-#   if (is.null(chat)) {
-#     with_chat_env$chat <- NULL
-#     return()
-#   }
-#   if (!inherits(chat, "Chat")) {
-#     cli::cli_abort(
-#       "Expected a Chat object, but got {.val {chat}}.",
-#       call = caller_env()
-#     )
-#   }
-#   with_chat_env$chat <- chat
-# }
-# with_chat_get <- function() {
-#   chat <- with_chat_env$chat
-#   if (is.null(chat)) {
-#     cli::cli_abort(
-#       "No Chat object found in the environment.",
-#       call = caller_env()
-#     )
-#   }
-#   chat
-# }
-# with_chat <- function(chat, code) {
-#   with_chat_set(chat)
-#   on.exit(with_chat_set(NULL), add = TRUE)
-#   force(code)
-# }
 
 method(contents_record, ToolDef) <- function(content, ..., chat) {
   list(
@@ -263,156 +186,6 @@ tool_rnorm <- tool(
   )
 )
 
-# method(contents_replay_impl, "S7") <- function(state) {
-#   if (!is.list(state)) {
-#     cli::cli_abort(
-#       "Expected a list, but got {.val {state}}.",
-#       call = caller_env()
-#     )
-#   }
-
-#   contents <- lapply(prop_names, function(prop_name) {
-#     prop_value <- S7::prop(prop_name, object = content)
-#     contents_replay(prop_value)
-#   })
-#   contents <- unlist(contents, recursive = FALSE)
-#   contents <- contents[!sapply(contents, is.null)]
-#   contents <- contents[contents != ""]
-#   contents
-# }
-
-# contents_list_replay <- function(state) {
-# }
-
-# contents_record_old <- new_generic("contents_record_old", "content")
-# method(contents_record_old_prop_names, S7_object) <- function(content) {
-#   S7::prop_names(content)
-# }
-
-# method(contents_record_old, S7_object) <- function(content) {
-#   prop_names <- contents_record_old_prop_names(content)
-#   if (length(prop_names) == 0) {
-#     return(NULL)
-#   }
-#   props <- lapply(prop_names, function(prop_name) {
-#     prop_value <- S7::prop(prop_name, object = content)
-#     contents_record_old(prop_value)
-#   })
-#   props <- setNames(props, prop_names)
-#   list(
-#     version = 1,
-#     type = "s7",
-#     class = class(content),
-#     props = props
-#   )
-# }
-
-# method(contents_record_old, S7::class_list) <- function(content) {
-#   lapply(content, contents_record_old)
-# }
-# method(contents_record_old, S7::class_any) <- function(content) {
-#   content
-# }
-
-# contents_replay_s7_cls <- function(state) {
-#   if (is.null(state)) {
-#     return(NULL)
-#   }
-#   if (state$version != 1) {
-#     cli::cli_abort(
-#       "Unsupported version {.val {state$version}}.",
-#       call = caller_env()
-#     )
-#   }
-
-#   if (!identical(state$type, "s7")) {
-#     cli::cli_abort(
-#       "Unsupported type {.val {state$type}}.",
-#       call = caller_env()
-#     )
-#   }
-
-#   class_value <- state$class
-#   if (is.null(class_value)) {
-#     cli::cli_abort(
-#       "class key must be provided. {.val {class_value}}."
-#     )
-#   }
-#   if (!is.character(class_value)) {
-#     cli::cli_abort(
-#       "class key must be a string. {.val {class_value}}."
-#     )
-#   }
-#   if (length(class_value) == 0) {
-#     cli::cli_abort(
-#       "class key must be a single string. {.val {class_value}}."
-#     )
-#   }
-#   if (nchar(class_value[0]) == 0) {
-#     cli::cli_abort(
-#       "class key must be a non-empty string. {.val {class_value}}."
-#     )
-#   }
-
-#   s7_cls_info <- strsplit(class_value[0], "::")[[1]]
-#   s7_cls_pkg <- s7_cls_info[1]
-#   s7_cls_name <- s7_cls_info[2]
-#   s7_cls <- rlang::pkg_env(s7_cls_pkg)[[s7_cls_name]]
-
-#   contents_replay(s7_cls, state)
-#   # s7_cls
-# }
-
-# method(contents_replay, S7::class_list) <- function(state) {
-#   lapply(state, contents_replay)
-# }
-# method(contents_replay, S7::class_any) <- function(cls, state) {
-#   state
-# }
-
-# method(contents_replay, S7_object) <- function(state, type) {
-#   prop_names <- contents_record_prop_names(content)
-#   if (length(prop_names) == 0) {
-#     return(NULL)
-#   }
-
-#   props <- lapply(prop_names, function(prop_name) {
-#     prop_value <- S7::prop(prop_name, object = content)
-#     contents_replay(prop_value)
-#   })
-
-#   rlang::inject(cls(!!!state$props))
-# }
-
-# method(contents_replay, Turn) <- function(object) {
-#   if (object$version != 1) {
-#     cli::cli_abort(
-#       "Unsupported version {.val {object$version}}.",
-#       call = caller_env()
-#     )
-#   }
-#   if (object$type != "turn") {
-#     cli::cli_abort(
-#       "Unsupported type {.val {object$type}}.",
-#       call = caller_env()
-#     )
-#   }
-#   contents <- lapply(content@contents, contents_replay)
-#   contents <- unlist(contents, recursive = FALSE)
-#   contents <- contents[!sapply(contents, is.null)]
-#   contents <- contents[contents != ""]
-#   contents
-# }
-# method(contents_replay, S7_object) <- function(content) {
-#   contents <- lapply(prop_names, function(prop_name) {
-#     prop_value <- S7::prop(prop_name, object = content)
-#     contents_replay(prop_value)
-#   })
-#   contents <- unlist(contents, recursive = FALSE)
-#   contents <- contents[!sapply(contents, is.null)]
-#   contents <- contents[contents != ""]
-#   contents
-# }
 
 expect_record_replay <- function(
   x,

From 2c3673c88a440197d9cef76fa976117d7f0ceaef Mon Sep 17 00:00:00 2001
From: Barret Schloerke <barret@posit.co>
Date: Mon, 19 May 2025 15:50:05 -0400
Subject: [PATCH 09/34] Add pre/post checks when recording

---
 R/content-replay.R | 47 +++++++++++++++++++++++++++++++++++-----------
 1 file changed, 36 insertions(+), 11 deletions(-)

diff --git a/R/content-replay.R b/R/content-replay.R
index 4b5786e0..e46db79e 100644
--- a/R/content-replay.R
+++ b/R/content-replay.R
@@ -11,18 +11,43 @@ NULL
 #' These generic functions can be use to convert [Turn] contents or [Content]
 #' objects into easily serializable representations.
 #'
-#' * `contents_replay()` will accept a basic object and return a corresponding
-#'   [Turn] or [Content] object.
-#' * `contents_record()` will accept a [Turn] or [Content] object and return a
-#'   basic object that can be easily serialized.
+#' * `contents_record()` will accept a [Turn] or [Content] related objects and return a
+#'   basic list that can be easily serialized.
+#' * `contents_replay()` will accept a basic list (from `contents_record()`) and
+#'   return a corresponding [Turn] or [Content] related object.
+#' * `contents_replay_class()` is a generic function that is dispatched from
+#'   within `contents_replay()`. `contents_replay()` will retrieve the
+#'   corresponding contructor class from within the basic list information and
+#'   use the class for dispatching.
 #' @export
-contents_record <- new_generic(
-  "contents_record",
-  "content",
-  function(content, ..., chat) {
-    S7::S7_dispatch()
-  }
-)
+contents_record <-
+  #' @export
+  #' @rdname contents_record
+  contents_record <- new_generic(
+    "contents_record",
+    "content",
+    function(content, ..., chat) {
+      if (!(R6::is.R6(chat) && inherits(chat, "Chat"))) {
+        cli::cli_abort(
+          "Expected a Chat object at `chat=`, but received {.val {chat}}.",
+          call = caller_env()
+        )
+      }
+
+      recorded <- S7::S7_dispatch()
+
+      for (name in c("version", "class", "props")) {
+        if (!name %in% names(recorded)) {
+          cli::cli_abort(
+            "Expected the recorded object to have a {.val {name}} property.",
+            call = caller_env()
+          )
+        }
+      }
+
+      recorded
+    }
+  )
 method(contents_record, S7::S7_object) <- function(content, ..., chat) {
   prop_names <- S7::prop_names(content)
   list(

From 2795f452cead0490a10b9f1bcad0800120b6450d Mon Sep 17 00:00:00 2001
From: Barret Schloerke <barret@posit.co>
Date: Mon, 19 May 2025 15:51:16 -0400
Subject: [PATCH 10/34] Rename dispatch method

---
 NAMESPACE              |  2 +-
 R/content-replay.R     | 11 ++++++-----
 man/contents_record.Rd | 16 ++++++++++------
 3 files changed, 17 insertions(+), 12 deletions(-)

diff --git a/NAMESPACE b/NAMESPACE
index 5cd0ed1f..cfc849ee 100644
--- a/NAMESPACE
+++ b/NAMESPACE
@@ -54,7 +54,7 @@ export(contents_html)
 export(contents_markdown)
 export(contents_record)
 export(contents_replay)
-export(contents_replay_s7)
+export(contents_replay_class)
 export(contents_text)
 export(create_tool_def)
 export(google_upload)
diff --git a/R/content-replay.R b/R/content-replay.R
index e46db79e..f2151e7d 100644
--- a/R/content-replay.R
+++ b/R/content-replay.R
@@ -83,6 +83,7 @@ method(contents_record, Turn) <- function(content, ..., chat) {
 
 #' @rdname contents_record
 #' @export
+# Holy "Holy Trait" dispatching, Batman!
 contents_replay <- function(obj, ..., chat) {
   if (!(R6::is.R6(chat) && inherits(chat, "Chat"))) {
     cli::cli_abort(
@@ -128,14 +129,14 @@ contents_replay <- function(obj, ..., chat) {
   # not on an instance
   # An error will be thrown if a method is not found,
   # however we have a fallback for the `S7::S7_object` (the root base class)
-  handler <- S7::method(contents_replay_s7, cls)
+  handler <- S7::method(contents_replay_class, cls)
   handler(cls, obj, chat = chat)
 }
 
 #' @rdname contents_record
 #' @export
-contents_replay_s7 <- new_generic(
-  "contents_replay_s7",
+contents_replay_class <- new_generic(
+  "contents_replay_class",
   "cls",
   function(cls, obj, ..., chat) {
     S7::S7_dispatch()
@@ -143,7 +144,7 @@ contents_replay_s7 <- new_generic(
 )
 
 
-method(contents_replay_s7, S7::S7_object) <- function(cls, obj, ..., chat) {
+method(contents_replay_class, S7::S7_object) <- function(cls, obj, ..., chat) {
   stopifnot(obj$version == 1)
 
   obj_props <- lapply(obj$props, contents_replay, chat = chat)
@@ -174,7 +175,7 @@ method(contents_record, ToolDef) <- function(content, ..., chat) {
     )
   )
 }
-method(contents_replay_s7, ToolDef) <- function(cls, obj, ..., chat) {
+method(contents_replay_class, ToolDef) <- function(cls, obj, ..., chat) {
   if (obj$version != 1) {
     cli::cli_abort(
       "Unsupported version {.val {obj$version}}.",
diff --git a/man/contents_record.Rd b/man/contents_record.Rd
index b9015793..639673eb 100644
--- a/man/contents_record.Rd
+++ b/man/contents_record.Rd
@@ -3,22 +3,26 @@
 \name{contents_record}
 \alias{contents_record}
 \alias{contents_replay}
-\alias{contents_replay_s7}
+\alias{contents_replay_class}
 \title{Save and restore content}
 \usage{
 contents_record(content, ..., chat)
 
 contents_replay(obj, ..., chat)
 
-contents_replay_s7(cls, obj, ..., chat)
+contents_replay_class(cls, obj, ..., chat)
 }
 \description{
 These generic functions can be use to convert \link{Turn} contents or \link{Content}
 objects into easily serializable representations.
 \itemize{
-\item \code{contents_replay()} will accept a basic object and return a corresponding
-\link{Turn} or \link{Content} object.
-\item \code{contents_record()} will accept a \link{Turn} or \link{Content} object and return a
-basic object that can be easily serialized.
+\item \code{contents_record()} will accept a \link{Turn} or \link{Content} related objects and return a
+basic list that can be easily serialized.
+\item \code{contents_replay()} will accept a basic list (from \code{contents_record()}) and
+return a corresponding \link{Turn} or \link{Content} related object.
+\item \code{contents_replay_class()} is a generic function that is dispatched from
+within \code{contents_replay()}. \code{contents_replay()} will retrieve the
+corresponding contructor class from within the basic list information and
+use the class for dispatching.
 }
 }

From 8cc0574be4eddc0109132dc83a8d93523c312527 Mon Sep 17 00:00:00 2001
From: Barret Schloerke <barret@posit.co>
Date: Mon, 19 May 2025 15:51:51 -0400
Subject: [PATCH 11/34] Fixed bug in tooldef args

---
 R/content-replay.R | 50 ++++++++++++++++++++++++++++++++++++----------
 1 file changed, 39 insertions(+), 11 deletions(-)

diff --git a/R/content-replay.R b/R/content-replay.R
index f2151e7d..bf60591d 100644
--- a/R/content-replay.R
+++ b/R/content-replay.R
@@ -169,7 +169,7 @@ method(contents_record, ToolDef) <- function(content, ..., chat) {
       # However, keep all the other properties as the metadata could be useful.
       fun = NULL,
       description = content@description,
-      arguments = content@arguments,
+      arguments = contents_record(content@arguments, chat = chat),
       convert = content@convert,
       annotations = content@annotations
     )
@@ -187,7 +187,7 @@ method(contents_replay_class, ToolDef) <- function(cls, obj, ..., chat) {
   matched_tool <- tools[[obj$props$name]]
 
   if (!is.null(matched_tool)) {
-    matched_tool
+    return(matched_tool)
   }
 
   # If no tool is found, return placeholder tool
@@ -195,22 +195,48 @@ method(contents_replay_class, ToolDef) <- function(cls, obj, ..., chat) {
     name = obj$props$name,
     # fun = NULL, # fun was not serialized
     description = obj$props$description,
-    # TODO: Barret fix this
     arguments = contents_replay(obj$props$arguments, chat = chat),
     convert = obj$props$convert,
     annotations = obj$props$annotations
   )
 }
 
-tool_rnorm <- tool(
-  stats::rnorm,
-  .description = "Drawn numbers from a random normal distribution",
-  n = type_integer("The number of observations. Must be a positive integer."),
-  mean = type_number("The mean value of the distribution."),
-  sd = type_number(
-    "The standard deviation of the distribution. Must be a non-negative number."
+
+method(contents_record, TypeObject) <- function(content, ..., chat) {
+  list(
+    version = 1,
+    class = class(content)[1],
+    props = list(
+      description = content@description,
+      required = content@required,
+      properties = lapply(
+        content@properties,
+        contents_record,
+        chat = chat
+      ),
+      additional_properties = content@additional_properties
+    )
   )
-)
+}
+method(contents_replay_class, TypeObject) <- function(cls, obj, ..., chat) {
+  if (obj$version != 1) {
+    cli::cli_abort(
+      "Unsupported version {.val {obj$version}}.",
+      call = caller_env()
+    )
+  }
+
+  TypeObject(
+    description = obj$props$description,
+    required = obj$props$required,
+    properties = lapply(
+      obj$props$properties,
+      contents_replay,
+      chat = chat
+    ),
+    additional_properties = obj$props$additional_properties
+  )
+}
 
 
 expect_record_replay <- function(
@@ -247,4 +273,6 @@ expect_record_replay <- function(
 
   expect_s3_class(replayed, class(x)[1])
   expect_equal(S7::props(replayed), S7::props(x))
+
+  invisible(replayed)
 }

From 618290bcdc266697567bc37c09bb04ed33dd535e Mon Sep 17 00:00:00 2001
From: Barret Schloerke <barret@posit.co>
Date: Mon, 19 May 2025 15:52:01 -0400
Subject: [PATCH 12/34] Don't record completed field

---
 R/content-replay.R | 3 +--
 1 file changed, 1 insertion(+), 2 deletions(-)

diff --git a/R/content-replay.R b/R/content-replay.R
index bf60591d..67f5dae5 100644
--- a/R/content-replay.R
+++ b/R/content-replay.R
@@ -74,8 +74,7 @@ method(contents_record, Turn) <- function(content, ..., chat) {
       role = content@role,
       contents = lapply(content@contents, contents_record, chat = chat),
       json = content@json,
-      tokens = content@tokens,
-      completed = content@completed,
+      tokens = content@tokens
       # text = getter only!
     )
   )

From 59e0b551a0ef8cc079f93223a03fc0b2496340a9 Mon Sep 17 00:00:00 2001
From: Barret Schloerke <barret@posit.co>
Date: Mon, 19 May 2025 16:00:24 -0400
Subject: [PATCH 13/34] Get the S7 class name in the traceback!

---
 R/content-replay.R | 22 +++++++++++++++++++---
 1 file changed, 19 insertions(+), 3 deletions(-)

diff --git a/R/content-replay.R b/R/content-replay.R
index 67f5dae5..2363e845 100644
--- a/R/content-replay.R
+++ b/R/content-replay.R
@@ -147,13 +147,29 @@ method(contents_replay_class, S7::S7_object) <- function(cls, obj, ..., chat) {
   stopifnot(obj$version == 1)
 
   obj_props <- lapply(obj$props, contents_replay, chat = chat)
+
   ## While this should give prettier tracebacks, it doesn't work
-  # > cls_name <- rlang::sym(obj$class[1])
-  # > rlang::inject((!!cls_name)(!!!obj_props))
+  # > pkg_cls_name <- rlang::sym(obj$class[1])
+  # > rlang::inject((!!pkg_cls_name)(!!!obj_props))
   # Error in `ellmer::Turn`(role = "user", contents = list(), json = list(),  :
   # could not find function "ellmer::Turn"
 
-  rlang::inject(cls(!!!obj_props))
+  # Instead, use the package environment when calling the constructo
+  pkg_cls <- strsplit(obj$class[1], "::")[[1]]
+  if (length(pkg_cls) != 2) {
+    rlang::cli_abort(
+      "Invalid class name {.val {obj$class[1]}}. Explected a single `::` separator.",
+      call = caller_env()
+    )
+  }
+  pkg_name <- pkg_cls[1]
+  cls_name <- pkg_cls[2]
+  withr::with_package(
+    pkg_name,
+    {
+      rlang::inject((!!rlang::sym(cls_name))(!!!obj_props))
+    }
+  )
 }
 
 

From adf7bac2b56a666a6fac2622164af0799a1906e1 Mon Sep 17 00:00:00 2001
From: Barret Schloerke <barret@posit.co>
Date: Mon, 19 May 2025 16:00:46 -0400
Subject: [PATCH 14/34] Complete some TODOs

---
 tests/testthat/test-content-replay.R | 56 ++++++++++++++++++----------
 1 file changed, 37 insertions(+), 19 deletions(-)

diff --git a/tests/testthat/test-content-replay.R b/tests/testthat/test-content-replay.R
index eef34e8f..a0e71f07 100644
--- a/tests/testthat/test-content-replay.R
+++ b/tests/testthat/test-content-replay.R
@@ -51,9 +51,22 @@ test_that("can round trip of ContentThinking record/replay", {
 })
 
 test_that("can round trip of ContentTool record/replay", {
+  chat <- chat_ollama_test("Be as terse as possible; no punctuation")
+  tool_rnorm <- tool(
+    stats::rnorm,
+    "Drawn numbers from a random normal distribution",
+    n = type_integer("The number of observations. Must be a positive integer."),
+    mean = type_number("The mean value of the distribution."),
+    sd = type_number(
+      "The standard deviation of the distribution. Must be a non-negative number."
+    )
+  )
+  chat$register_tool(tool_rnorm)
+
   # TODO: barret - test tooldef, need to adjust replay to accept client to recontruct tooldef
   expect_record_replay(
-    ContentToolRequest("ID", "tool_name", list(a = 1:2, b = "apple"))
+    ContentToolRequest("ID", "tool_name", list(a = 1:2, b = "apple")),
+    chat = chat
   )
 })
 
@@ -70,11 +83,8 @@ test_that("can round trip of ToolDef record/replay", {
   )
   chat$register_tool(tool_rnorm)
 
-  # with_chat(chat, {
   expect_record_replay(tool_rnorm, chat = chat)
-  # })
 
-  # with_chat(chat, {
   expect_record_replay(
     ContentToolRequest(
       "ID",
@@ -84,7 +94,6 @@ test_that("can round trip of ToolDef record/replay", {
     ),
     chat = chat
   )
-  # })
 })
 
 test_that("can round trip of ContentToolResult record/replay", {
@@ -109,22 +118,31 @@ test_that("can round trip of ContentToolResult record/replay", {
   )
   chat$register_tool(tool_rnorm)
 
-  expect_record_replay(
-    ContentToolResult(
-      value = "VALUE",
-      error = try(stop("boom"), silent = TRUE),
-      extra = list(extra = 1:2, b = "apple"),
-      request = ContentToolRequest(
-        "ID",
-        "tool_name",
-        list(a = 1:2, b = "apple"),
-        tool = tool_rnorm
+  replayed <-
+    expect_record_replay(
+      ContentToolResult(
+        value = "VALUE",
+        error = try(stop("boom"), silent = TRUE),
+        extra = list(extra = 1:2, b = "apple"),
+        request = ContentToolRequest(
+          "ID",
+          "tool_name",
+          list(a = 1:2, b = "apple"),
+          tool = tool_rnorm
+        )
+      ),
+      chat = chat
+    )
+
+  tryCatch(
+    message(replayed@error), # re-throw error
+    error = function(e) {
+      expect_equal(
+        e$message,
+        "boom"
       )
-    ),
-    chat = chat
+    }
   )
-  # TODO: Barret test real error value
-  # TODO: Barret test with request object
 })
 
 test_that("can round trip of ContentUploaded record/replay", {

From e084919a7af5c9d4cf6c43df0266079fd635c904 Mon Sep 17 00:00:00 2001
From: Barret Schloerke <barret@posit.co>
Date: Tue, 20 May 2025 10:01:54 -0400
Subject: [PATCH 15/34] Update content-replay.R

---
 R/content-replay.R | 5 ++---
 1 file changed, 2 insertions(+), 3 deletions(-)

diff --git a/R/content-replay.R b/R/content-replay.R
index 2363e845..933637ed 100644
--- a/R/content-replay.R
+++ b/R/content-replay.R
@@ -20,10 +20,9 @@ NULL
 #'   corresponding contructor class from within the basic list information and
 #'   use the class for dispatching.
 #' @export
+#' @rdname contents_record
 contents_record <-
-  #' @export
-  #' @rdname contents_record
-  contents_record <- new_generic(
+  new_generic(
     "contents_record",
     "content",
     function(content, ..., chat) {

From 66b9649afe27917099a763a9c567ca3e67475217 Mon Sep 17 00:00:00 2001
From: Barret Schloerke <barret@posit.co>
Date: Tue, 20 May 2025 12:39:48 -0400
Subject: [PATCH 16/34] Allow for objects to be non-pkg S7 classes

---
 R/content-replay.R     | 181 ++++++++++++++++++++++++++++++++---------
 man/contents_record.Rd |  47 ++++++++++-
 2 files changed, 189 insertions(+), 39 deletions(-)

diff --git a/R/content-replay.R b/R/content-replay.R
index 933637ed..a37549c4 100644
--- a/R/content-replay.R
+++ b/R/content-replay.R
@@ -19,6 +19,43 @@ NULL
 #'   within `contents_replay()`. `contents_replay()` will retrieve the
 #'   corresponding contructor class from within the basic list information and
 #'   use the class for dispatching.
+#'
+#' Note, all S7 classes should have the same class name as the variable name. Ex: `FooBar <- new_class("FooBar")`, not `OtherName <- new_class("FooBar")`. This is a requirement for when replaying the object.
+#'
+#' @param content A [Turn] or [Content] object to be recorded.
+#' @param obj A basic list (from `contents_record()`) to be replayed.
+#' @param cls The class constructor to be used for replaying the object.
+#' @param chat A [Chat] object to be used for recording and replaying.
+#' @param env The environment to find non-package classes.
+#' @param ... Not used.
+#'
+#' @examples
+#' \dontrun{
+#' chat <- chat_ollama(model = "llama3.2")
+#' turn <- Turn("user")
+#' turn
+#' #> <Turn: user>
+#'
+#' # Get the turn record
+#' # Note: Removes all S7 class instances
+#' turn_recorded <- contents_record(turn, chat = chat)
+#' str(turn_recorded)
+#' #> List of 3
+#' #>  $ version: num 1
+#' #>  $ class  : chr "ellmer::Turn"
+#' #>  $ props  :List of 4
+#' #>   ..$ role    : chr "user"
+#' #>   ..$ contents: list()
+#' #>   ..$ json    : list()
+#' #>   ..$ tokens  : num [1:2] 0 0
+#'
+#' # Restore the turn from the record
+#' # Note: This will not restore the _original_ object,
+#' # but a new object with the same properties
+#' turn_replayed <- contents_replay(turn_recorded, chat = chat)
+#' turn_replayed
+#' #> <Turn: user>
+#' }
 #' @export
 #' @rdname contents_record
 contents_record <-
@@ -43,12 +80,22 @@ contents_record <-
           )
         }
       }
+      if (
+        !is.character(recorded$class) ||
+          length(recorded$class) != 1
+      ) {
+        cli::cli_abort(
+          "Expected the recorded object to have a single $class name, containing `::` if the class is from a package.",
+          call = caller_env()
+        )
+      }
 
       recorded
     }
   )
 method(contents_record, S7::S7_object) <- function(content, ..., chat) {
   prop_names <- S7::prop_names(content)
+  class_name <- class(content)[1]
   list(
     version = 1,
     class = class(content)[1],
@@ -82,7 +129,13 @@ method(contents_record, Turn) <- function(content, ..., chat) {
 #' @rdname contents_record
 #' @export
 # Holy "Holy Trait" dispatching, Batman!
-contents_replay <- function(obj, ..., chat) {
+contents_replay <- function(
+  obj,
+  ...,
+  cls = NULL,
+  chat,
+  env = rlang::caller_env()
+) {
   if (!(R6::is.R6(chat) && inherits(chat, "Chat"))) {
     cli::cli_abort(
       "Expected a Chat object at `chat=`, but received {.val {chat}}.",
@@ -106,14 +159,7 @@ contents_replay <- function(obj, ..., chat) {
     return(obj)
   }
 
-  pkg_cls <- strsplit(class_value[1], "::")[[1]]
-  if (length(pkg_cls) != 2) {
-    return(obj)
-  }
-  pkg_name <- pkg_cls[1]
-  cls_name <- pkg_cls[2]
-
-  cls <- rlang::pkg_env(pkg_name)[[cls_name]]
+  cls <- get_cls_constructor(class_value[1], env = env)
 
   if (is.null(cls)) {
     return(obj)
@@ -128,7 +174,7 @@ contents_replay <- function(obj, ..., chat) {
   # An error will be thrown if a method is not found,
   # however we have a fallback for the `S7::S7_object` (the root base class)
   handler <- S7::method(contents_replay_class, cls)
-  handler(cls, obj, chat = chat)
+  handler(cls, obj, chat = chat, env = env)
 }
 
 #' @rdname contents_record
@@ -136,38 +182,46 @@ contents_replay <- function(obj, ..., chat) {
 contents_replay_class <- new_generic(
   "contents_replay_class",
   "cls",
-  function(cls, obj, ..., chat) {
+  function(cls, obj, ..., chat, env = rlang::caller_env()) {
     S7::S7_dispatch()
   }
 )
 
 
-method(contents_replay_class, S7::S7_object) <- function(cls, obj, ..., chat) {
+method(contents_replay_class, S7::S7_object) <- function(
+  cls,
+  obj,
+  ...,
+  chat,
+  env = rlang::caller_env()
+) {
   stopifnot(obj$version == 1)
 
   obj_props <- lapply(obj$props, contents_replay, chat = chat)
 
-  ## While this should give prettier tracebacks, it doesn't work
-  # > pkg_cls_name <- rlang::sym(obj$class[1])
-  # > rlang::inject((!!pkg_cls_name)(!!!obj_props))
-  # Error in `ellmer::Turn`(role = "user", contents = list(), json = list(),  :
-  # could not find function "ellmer::Turn"
-
-  # Instead, use the package environment when calling the constructo
-  pkg_cls <- strsplit(obj$class[1], "::")[[1]]
-  if (length(pkg_cls) != 2) {
-    rlang::cli_abort(
-      "Invalid class name {.val {obj$class[1]}}. Explected a single `::` separator.",
-      call = caller_env()
+  class_value <- obj$class[1]
+  if (grepl("::", class_value, fixed = TRUE)) {
+    # If the class is a package class, use the package name to find the constructor
+    # This allows use to reach into private namespaces within the package
+    pkg_cls <- strsplit(class_value, "::")[[1]]
+    pkg_name <- pkg_cls[1]
+
+    rlang::check_installed(
+      pkg_name,
+      reason = "for `contents_replay()` to restore the chat content."
     )
+    cls_name <- pkg_cls[2]
+    env <- rlang::pkg_env(pkg_name)
+  } else {
+    cls_name <- class_value
   }
-  pkg_name <- pkg_cls[1]
-  cls_name <- pkg_cls[2]
-  withr::with_package(
-    pkg_name,
-    {
-      rlang::inject((!!rlang::sym(cls_name))(!!!obj_props))
-    }
+
+  # While this seems like a bit of extra work, the tracebacks are accurate
+  # vs referencing an unrelated parameter name in the traceback
+  rlang::exec(
+    cls_name,
+    !!!obj_props,
+    .env = env
   )
 }
 
@@ -189,7 +243,13 @@ method(contents_record, ToolDef) <- function(content, ..., chat) {
     )
   )
 }
-method(contents_replay_class, ToolDef) <- function(cls, obj, ..., chat) {
+method(contents_replay_class, ToolDef) <- function(
+  cls,
+  obj,
+  ...,
+  chat,
+  env = rlang::caller_env()
+) {
   if (obj$version != 1) {
     cli::cli_abort(
       "Unsupported version {.val {obj$version}}.",
@@ -232,7 +292,13 @@ method(contents_record, TypeObject) <- function(content, ..., chat) {
     )
   )
 }
-method(contents_replay_class, TypeObject) <- function(cls, obj, ..., chat) {
+method(contents_replay_class, TypeObject) <- function(
+  cls,
+  obj,
+  ...,
+  chat,
+  env = rlang::caller_env()
+) {
   if (obj$version != 1) {
     cli::cli_abort(
       "Unsupported version {.val {obj$version}}.",
@@ -253,10 +319,49 @@ method(contents_replay_class, TypeObject) <- function(cls, obj, ..., chat) {
 }
 
 
+#' Retrieve the class constructor
+#'
+#' @description
+#' The class for S7 Classes are stored as "package::class" in the recorded object.
+#' However, it does not mean that the class constructor is exported in the namespace.
+#' Therefore, this function will reach into the package environment to retrieve the constructor.
+#' If the class is not a _package_ class, it will return the object as is given the `env`.
+#'
+#' @param class_value The single string representing the `package::class` to retrieve the constructor.
+#' @param ... Not used.
+#' @param env The environment to find non-package class constructors.
+#' @return The constructor function for the class.
+#' @noRd
+get_cls_constructor <- function(class_value, ..., env = rlang::caller_env()) {
+  rlang::check_dots_empty()
+
+  pkg_cls <- strsplit(class_value, "::")[[1]]
+  if (length(pkg_cls) == 1) {
+    # If the class is not a package class, return the object as is
+    # This is the case for local S7 objects
+    rlang::eval_bare(rlang::sym(pkg_cls), env = env)
+  } else if (length(pkg_cls) == 2) {
+    pkg_name <- pkg_cls[1]
+    cls_name <- pkg_cls[2]
+
+    rlang::check_installed(
+      pkg_name,
+      reason = "for `contents_replay()` to restore the chat content."
+    )
+    rlang::pkg_env(pkg_name)[[cls_name]]
+  } else {
+    cli::cli_abort(
+      "Invalid class name {.val {class_value[1]}}. Expected a single (or missing) `::` separator, not multiple.",
+      call = caller_env()
+    )
+  }
+}
+
 expect_record_replay <- function(
   x,
   ...,
-  chat = chat_ollama_test("Be as terse as possible; no punctuation")
+  chat = chat_ollama_test("Be as terse as possible; no punctuation"),
+  env = rlang::caller_env()
 ) {
   rlang::check_dots_empty()
 
@@ -274,16 +379,18 @@ expect_record_replay <- function(
 
   # Work around Shiny's terrible JSON serialization
   # Use `as.character()` to remove the JSON class so that it is double serialized :-/
-  marshalled = as.character(jsonlite::serializeJSON(obj))
+  marshalled <- list(
+    "my_chat" = as.character(jsonlite::serializeJSON(obj))
+  )
 
   # Bookmark
   serialized <- shiny:::toJSON(marshalled)
   unserialized <- shiny:::safeFromJSON(serialized)
 
   # obj_unpacked <- jsonlite:::unpack(unserialized)
-  unmarshalled <- jsonlite::unserializeJSON(unserialized)
+  unmarshalled <- jsonlite::unserializeJSON(unserialized$my_chat)
 
-  replayed <- contents_replay(unmarshalled, chat = chat)
+  replayed <- contents_replay(unmarshalled, chat = chat, env = env)
 
   expect_s3_class(replayed, class(x)[1])
   expect_equal(S7::props(replayed), S7::props(x))
diff --git a/man/contents_record.Rd b/man/contents_record.Rd
index 639673eb..b0c243fe 100644
--- a/man/contents_record.Rd
+++ b/man/contents_record.Rd
@@ -8,9 +8,22 @@
 \usage{
 contents_record(content, ..., chat)
 
-contents_replay(obj, ..., chat)
+contents_replay(obj, ..., cls = NULL, chat, env = rlang::caller_env())
 
-contents_replay_class(cls, obj, ..., chat)
+contents_replay_class(cls, obj, ..., chat, env = rlang::caller_env())
+}
+\arguments{
+\item{content}{A \link{Turn} or \link{Content} object to be recorded.}
+
+\item{...}{Not used.}
+
+\item{chat}{A \link{Chat} object to be used for recording and replaying.}
+
+\item{obj}{A basic list (from \code{contents_record()}) to be replayed.}
+
+\item{cls}{The class constructor to be used for replaying the object.}
+
+\item{env}{The environment to find non-package classes.}
 }
 \description{
 These generic functions can be use to convert \link{Turn} contents or \link{Content}
@@ -25,4 +38,34 @@ within \code{contents_replay()}. \code{contents_replay()} will retrieve the
 corresponding contructor class from within the basic list information and
 use the class for dispatching.
 }
+
+Note, all S7 classes should have the same class name as the variable name. Ex: \code{FooBar <- new_class("FooBar")}, not \code{OtherName <- new_class("FooBar")}. This is a requirement for when replaying the object.
+}
+\examples{
+\dontrun{
+chat <- chat_ollama(model = "llama3.2")
+turn <- Turn("user")
+turn
+#> <Turn: user>
+
+# Get the turn record
+# Note: Removes all S7 class instances
+turn_recorded <- contents_record(turn, chat = chat)
+str(turn_recorded)
+#> List of 3
+#>  $ version: num 1
+#>  $ class  : chr "ellmer::Turn"
+#>  $ props  :List of 4
+#>   ..$ role    : chr "user"
+#>   ..$ contents: list()
+#>   ..$ json    : list()
+#>   ..$ tokens  : num [1:2] 0 0
+
+# Restore the turn from the record
+# Note: This will not restore the _original_ object,
+# but a new object with the same properties
+turn_replayed <- contents_replay(turn_recorded, chat = chat)
+turn_replayed
+#> <Turn: user>
+}
 }

From 0dd25a4e53af1daee33787ce6369434c9f142a53 Mon Sep 17 00:00:00 2001
From: Barret Schloerke <barret@posit.co>
Date: Tue, 20 May 2025 12:40:04 -0400
Subject: [PATCH 17/34] Error when S7 classes can't be found

---
 R/content-replay.R | 10 ++++++++--
 1 file changed, 8 insertions(+), 2 deletions(-)

diff --git a/R/content-replay.R b/R/content-replay.R
index a37549c4..7ea165eb 100644
--- a/R/content-replay.R
+++ b/R/content-replay.R
@@ -162,11 +162,17 @@ contents_replay <- function(
   cls <- get_cls_constructor(class_value[1], env = env)
 
   if (is.null(cls)) {
-    return(obj)
+    cli::cli_abort(
+      "Unable to find the S7 class: {.val {class_value[1]}}.",
+      call = caller_env()
+    )
   }
 
   if (!S7_inherits(cls)) {
-    return(obj)
+    cli::cli_abort(
+      "The object returned for {.val {class_value[1]}} is not an S7 class.",
+      call = caller_env()
+    )
   }
 
   # Manually retrieve the handler for the class as we dispatch on the class itself,

From a7b24cb07c2a868a98e9fc968a649e1419a598ff Mon Sep 17 00:00:00 2001
From: Barret Schloerke <barret@posit.co>
Date: Tue, 20 May 2025 12:40:15 -0400
Subject: [PATCH 18/34] Update test-content-replay.R

---
 tests/testthat/test-content-replay.R | 53 ++++++++++++++++++++++++++--
 1 file changed, 51 insertions(+), 2 deletions(-)

diff --git a/tests/testthat/test-content-replay.R b/tests/testthat/test-content-replay.R
index a0e71f07..d7b11a5f 100644
--- a/tests/testthat/test-content-replay.R
+++ b/tests/testthat/test-content-replay.R
@@ -63,7 +63,6 @@ test_that("can round trip of ContentTool record/replay", {
   )
   chat$register_tool(tool_rnorm)
 
-  # TODO: barret - test tooldef, need to adjust replay to accept client to recontruct tooldef
   expect_record_replay(
     ContentToolRequest("ID", "tool_name", list(a = 1:2, b = "apple")),
     chat = chat
@@ -135,7 +134,7 @@ test_that("can round trip of ContentToolResult record/replay", {
     )
 
   tryCatch(
-    message(replayed@error), # re-throw error
+    signalCondition(replayed@error), # re-throw error
     error = function(e) {
       expect_equal(
         e$message,
@@ -152,3 +151,53 @@ test_that("can round trip of ContentUploaded record/replay", {
 test_that("can round trip of ContentPDF record/replay", {
   expect_record_replay(ContentPDF(type = "TYPE", data = "DATA"))
 })
+
+test_that("non-package classes are recorded/replayed by default", {
+  chat <- chat_ollama_test("Be as terse as possible; no punctuation")
+
+  LocalClass <- S7::new_class(
+    "LocalClass",
+    properties = list(
+      name = prop_string()
+    ),
+    # Make sure to unset the package being used!
+    # Within testing, it sets the package to "ellmer"
+    package = NULL
+  )
+
+  expect_record_replay(LocalClass("testname"), chat = chat)
+})
+
+
+test_that("unknown classes cause errors", {
+  chat <- chat_ollama_test("Be as terse as possible; no punctuation")
+  recorded <- contents_record(Turn("user"), chat = chat)
+  recorded$class <- "ellmer::Turn2"
+
+  expect_error(
+    contents_replay(recorded, chat = chat),
+    "Unable to find the S7 class"
+  )
+})
+
+test_that("replay classes are S7 classes", {
+  OtherName <- S7::new_class(
+    "LocalClass",
+    properties = list(
+      name = prop_string()
+    ),
+    # Make sure to unset the package being used!
+    # Within testing, it sets the package to "ellmer"
+    package = NULL
+  )
+  LocalClass <- function(name) {
+    OtherName(name = name)
+  }
+
+  chat <- chat_ollama_test("Be as terse as possible; no punctuation")
+  recorded <- contents_record(LocalClass("testname"), chat = chat)
+  expect_error(
+    contents_replay(recorded, chat = chat),
+    "is not an S7 class"
+  )
+})

From f268b963253e295890f5bc3439d8f9d604c0f1a5 Mon Sep 17 00:00:00 2001
From: Barret Schloerke <barret@posit.co>
Date: Tue, 20 May 2025 12:54:59 -0400
Subject: [PATCH 19/34] Move test helper to helper file. Rename it

---
 R/content-replay.R                     | 45 ++------------------------
 tests/testthat/helper-content-replay.R | 43 ++++++++++++++++++++++++
 tests/testthat/test-content-replay.R   | 32 +++++++++---------
 3 files changed, 61 insertions(+), 59 deletions(-)
 create mode 100644 tests/testthat/helper-content-replay.R

diff --git a/R/content-replay.R b/R/content-replay.R
index 7ea165eb..ac6eb836 100644
--- a/R/content-replay.R
+++ b/R/content-replay.R
@@ -217,7 +217,7 @@ method(contents_replay_class, S7::S7_object) <- function(
       reason = "for `contents_replay()` to restore the chat content."
     )
     cls_name <- pkg_cls[2]
-    env <- rlang::pkg_env(pkg_name)
+    env <- rlang::ns_env(pkg_name)
   } else {
     cls_name <- class_value
   }
@@ -354,7 +354,7 @@ get_cls_constructor <- function(class_value, ..., env = rlang::caller_env()) {
       pkg_name,
       reason = "for `contents_replay()` to restore the chat content."
     )
-    rlang::pkg_env(pkg_name)[[cls_name]]
+    rlang::ns_env(pkg_name)[[cls_name]]
   } else {
     cli::cli_abort(
       "Invalid class name {.val {class_value[1]}}. Expected a single (or missing) `::` separator, not multiple.",
@@ -362,44 +362,3 @@ get_cls_constructor <- function(class_value, ..., env = rlang::caller_env()) {
     )
   }
 }
-
-expect_record_replay <- function(
-  x,
-  ...,
-  chat = chat_ollama_test("Be as terse as possible; no punctuation"),
-  env = rlang::caller_env()
-) {
-  rlang::check_dots_empty()
-
-  # Simulate the full bookmarking experience:
-  # * Record the object to something serializable
-  # * Serialize the object to JSON via shiny; "bookmark"
-  # * Unserialize the object from JSON via shiny; "restore"
-  # * Replay the unserialized object to the original object
-  # * Check that the replayed object has the same class as the original object
-  # * Check that the replayed object has the same properties as the original object
-
-  obj <- contents_record(x, chat = chat)
-
-  # obj_packed <- jsonlite:::pack(obj)
-
-  # Work around Shiny's terrible JSON serialization
-  # Use `as.character()` to remove the JSON class so that it is double serialized :-/
-  marshalled <- list(
-    "my_chat" = as.character(jsonlite::serializeJSON(obj))
-  )
-
-  # Bookmark
-  serialized <- shiny:::toJSON(marshalled)
-  unserialized <- shiny:::safeFromJSON(serialized)
-
-  # obj_unpacked <- jsonlite:::unpack(unserialized)
-  unmarshalled <- jsonlite::unserializeJSON(unserialized$my_chat)
-
-  replayed <- contents_replay(unmarshalled, chat = chat, env = env)
-
-  expect_s3_class(replayed, class(x)[1])
-  expect_equal(S7::props(replayed), S7::props(x))
-
-  invisible(replayed)
-}
diff --git a/tests/testthat/helper-content-replay.R b/tests/testthat/helper-content-replay.R
new file mode 100644
index 00000000..feaa1040
--- /dev/null
+++ b/tests/testthat/helper-content-replay.R
@@ -0,0 +1,43 @@
+test_record_replay <- function(
+  x,
+  ...,
+  chat = chat_ollama_test("Be as terse as possible; no punctuation"),
+  env = rlang::caller_env()
+) {
+  rlang::check_dots_empty()
+
+  shiny__to_json <- rlang::ns_env("shiny")[["toJSON"]]
+  shiny__safe_from_json <- rlang::ns_env("shiny")[["safeFromJSON"]]
+
+  # Simulate the full bookmarking experience:
+  # * Record the object to something serializable
+  # * Serialize the object to JSON via shiny; "bookmark"
+  # * Unserialize the object from JSON via shiny; "restore"
+  # * Replay the unserialized object to the original object
+  # * Check that the replayed object has the same class as the original object
+  # * Check that the replayed object has the same properties as the original object
+
+  obj <- contents_record(x, chat = chat)
+
+  # obj_packed <- jsonlite:::pack(obj)
+
+  # Work around Shiny's terrible JSON serialization
+  # Use `as.character()` to remove the JSON class so that it is double serialized :-/
+  marshalled <- list(
+    "my_chat" = as.character(jsonlite::serializeJSON(obj))
+  )
+
+  # Bookmark
+  serialized <- shiny__to_json(marshalled)
+  unserialized <- shiny__safe_from_json(serialized)
+
+  # obj_unpacked <- jsonlite:::unpack(unserialized)
+  unmarshalled <- jsonlite::unserializeJSON(unserialized$my_chat)
+
+  replayed <- contents_replay(unmarshalled, chat = chat, env = env)
+
+  expect_s3_class(replayed, class(x)[1])
+  expect_equal(S7::props(replayed), S7::props(x))
+
+  invisible(replayed)
+}
diff --git a/tests/testthat/test-content-replay.R b/tests/testthat/test-content-replay.R
index d7b11a5f..a19496ae 100644
--- a/tests/testthat/test-content-replay.R
+++ b/tests/testthat/test-content-replay.R
@@ -1,39 +1,39 @@
 # -------------------------------------------------------------------------
 
 test_that("can round trip of Content record/replay", {
-  expect_record_replay(Content())
+  test_record_replay(Content())
 })
 
 test_that("can round trip of ContentText record/replay", {
-  expect_record_replay(ContentText("hello world"))
+  test_record_replay(ContentText("hello world"))
 })
 
 test_that("can round trip of ContentImageInline record/replay", {
-  expect_record_replay(
+  test_record_replay(
     ContentImageInline("image/png", "abcd123")
   )
 })
 
 test_that("can round trip of ContentImageRemote record/replay", {
-  expect_record_replay(
+  test_record_replay(
     ContentImageRemote("https://example.com/image.jpg", detail = "")
   )
 })
 
 test_that("can round trip of ContentJson record/replay", {
-  expect_record_replay(
+  test_record_replay(
     ContentJson(list(a = 1:2, b = "apple"))
   )
 })
 
 test_that("can round trip of ContentSql record/replay", {
-  expect_record_replay(
+  test_record_replay(
     ContentSql("SELECT * FROM mtcars")
   )
 })
 
 test_that("can round trip of ContentSuggestions record/replay", {
-  expect_record_replay(
+  test_record_replay(
     ContentSuggestions(
       c(
         "What is the total quantity sold for each product last quarter?",
@@ -45,7 +45,7 @@ test_that("can round trip of ContentSuggestions record/replay", {
 })
 
 test_that("can round trip of ContentThinking record/replay", {
-  expect_record_replay(
+  test_record_replay(
     ContentThinking("A **thought**.")
   )
 })
@@ -63,7 +63,7 @@ test_that("can round trip of ContentTool record/replay", {
   )
   chat$register_tool(tool_rnorm)
 
-  expect_record_replay(
+  test_record_replay(
     ContentToolRequest("ID", "tool_name", list(a = 1:2, b = "apple")),
     chat = chat
   )
@@ -82,9 +82,9 @@ test_that("can round trip of ToolDef record/replay", {
   )
   chat$register_tool(tool_rnorm)
 
-  expect_record_replay(tool_rnorm, chat = chat)
+  test_record_replay(tool_rnorm, chat = chat)
 
-  expect_record_replay(
+  test_record_replay(
     ContentToolRequest(
       "ID",
       "tool_name",
@@ -96,7 +96,7 @@ test_that("can round trip of ToolDef record/replay", {
 })
 
 test_that("can round trip of ContentToolResult record/replay", {
-  expect_record_replay(
+  test_record_replay(
     ContentToolResult(
       value = "VALUE",
       error = NULL,
@@ -118,7 +118,7 @@ test_that("can round trip of ContentToolResult record/replay", {
   chat$register_tool(tool_rnorm)
 
   replayed <-
-    expect_record_replay(
+    test_record_replay(
       ContentToolResult(
         value = "VALUE",
         error = try(stop("boom"), silent = TRUE),
@@ -145,11 +145,11 @@ test_that("can round trip of ContentToolResult record/replay", {
 })
 
 test_that("can round trip of ContentUploaded record/replay", {
-  expect_record_replay(ContentUploaded("https://example.com/image.jpg"))
+  test_record_replay(ContentUploaded("https://example.com/image.jpg"))
 })
 
 test_that("can round trip of ContentPDF record/replay", {
-  expect_record_replay(ContentPDF(type = "TYPE", data = "DATA"))
+  test_record_replay(ContentPDF(type = "TYPE", data = "DATA"))
 })
 
 test_that("non-package classes are recorded/replayed by default", {
@@ -165,7 +165,7 @@ test_that("non-package classes are recorded/replayed by default", {
     package = NULL
   )
 
-  expect_record_replay(LocalClass("testname"), chat = chat)
+  test_record_replay(LocalClass("testname"), chat = chat)
 })
 
 

From e9cba4093f90c1a453bc6d17c75a87501d2dab86 Mon Sep 17 00:00:00 2001
From: Barret Schloerke <barret@posit.co>
Date: Tue, 20 May 2025 13:17:06 -0400
Subject: [PATCH 20/34] Add Barret as author

---
 DESCRIPTION           | 2 ++
 man/ellmer-package.Rd | 2 ++
 2 files changed, 4 insertions(+)

diff --git a/DESCRIPTION b/DESCRIPTION
index 9052dfc5..0c658a98 100644
--- a/DESCRIPTION
+++ b/DESCRIPTION
@@ -8,6 +8,8 @@ Authors@R: c(
     person("Aaron", "Jacobs", role = "aut"),
     person("Garrick", "Aden-Buie", , "garrick@posit.co", role = "aut",
            comment = c(ORCID = "0000-0002-7111-0077")),
+    person("Barret", "Schloerke", , "barret@posit.co", role = "aut",
+           comment = c(ORCID = "0000-0001-9986-114X")),
     person("Posit Software, PBC", role = c("cph", "fnd"),
            comment = c(ROR = "03wc8by49"))
   )
diff --git a/man/ellmer-package.Rd b/man/ellmer-package.Rd
index 606bac89..f609548d 100644
--- a/man/ellmer-package.Rd
+++ b/man/ellmer-package.Rd
@@ -26,6 +26,8 @@ Authors:
 \itemize{
   \item Joe Cheng
   \item Aaron Jacobs
+  \item Garrick Aden-Buie \email{garrick@posit.co} (\href{https://orcid.org/0000-0002-7111-0077}{ORCID})
+  \item Barret Schloerke \email{barret@posit.co} (\href{https://orcid.org/0000-0001-9986-114X}{ORCID})
 }
 
 Other contributors:

From f51229eccb5aa992fe5a6fde5a9a139385f27d7d Mon Sep 17 00:00:00 2001
From: Barret Schloerke <barret@posit.co>
Date: Tue, 20 May 2025 13:17:14 -0400
Subject: [PATCH 21/34] Update _pkgdown.yml

---
 _pkgdown.yml | 1 +
 1 file changed, 1 insertion(+)

diff --git a/_pkgdown.yml b/_pkgdown.yml
index ad52a902..94a63ed4 100644
--- a/_pkgdown.yml
+++ b/_pkgdown.yml
@@ -59,6 +59,7 @@ reference:
   - title: Utilities
     contents:
       - contents_text
+      - contents_record
       - params
 
   - title: Deprecated functions

From ae4dc7ebd6ec08306ea10fef6f6c4fab276ab227 Mon Sep 17 00:00:00 2001
From: Barret Schloerke <barret@posit.co>
Date: Tue, 20 May 2025 14:14:31 -0400
Subject: [PATCH 22/34] Add news entry

---
 NEWS.md                | 6 ++++++
 R/content-replay.R     | 6 +++---
 man/contents_record.Rd | 6 +++---
 3 files changed, 12 insertions(+), 6 deletions(-)

diff --git a/NEWS.md b/NEWS.md
index ba5a9a33..9f881c70 100644
--- a/NEWS.md
+++ b/NEWS.md
@@ -1,5 +1,11 @@
 # ellmer (development version)
 
+## New features
+
+## Developer tooling
+
+* Added `contents_record()`, `contents_replay()`, and `contents_replay_class()` to record and replay `Turn` related information from a `Chat` instance (#502). For example, these methods can be used for bookmarking within `{shinychat}`.
+
 # ellmer 0.2.0
 
 ## Breaking changes
diff --git a/R/content-replay.R b/R/content-replay.R
index ac6eb836..10e61cd6 100644
--- a/R/content-replay.R
+++ b/R/content-replay.R
@@ -22,10 +22,10 @@ NULL
 #'
 #' Note, all S7 classes should have the same class name as the variable name. Ex: `FooBar <- new_class("FooBar")`, not `OtherName <- new_class("FooBar")`. This is a requirement for when replaying the object.
 #'
-#' @param content A [Turn] or [Content] object to be recorded.
+#' @param content A [Turn] or [Content] object to have its record retrieved.
 #' @param obj A basic list (from `contents_record()`) to be replayed.
 #' @param cls The class constructor to be used for replaying the object.
-#' @param chat A [Chat] object to be used for recording and replaying.
+#' @param chat A [Chat] object to be used for context.
 #' @param env The environment to find non-package classes.
 #' @param ... Not used.
 #'
@@ -36,7 +36,7 @@ NULL
 #' turn
 #' #> <Turn: user>
 #'
-#' # Get the turn record
+#' # Get the turn's record
 #' # Note: Removes all S7 class instances
 #' turn_recorded <- contents_record(turn, chat = chat)
 #' str(turn_recorded)
diff --git a/man/contents_record.Rd b/man/contents_record.Rd
index b0c243fe..99d4deb5 100644
--- a/man/contents_record.Rd
+++ b/man/contents_record.Rd
@@ -13,11 +13,11 @@ contents_replay(obj, ..., cls = NULL, chat, env = rlang::caller_env())
 contents_replay_class(cls, obj, ..., chat, env = rlang::caller_env())
 }
 \arguments{
-\item{content}{A \link{Turn} or \link{Content} object to be recorded.}
+\item{content}{A \link{Turn} or \link{Content} object to have its record retrieved.}
 
 \item{...}{Not used.}
 
-\item{chat}{A \link{Chat} object to be used for recording and replaying.}
+\item{chat}{A \link{Chat} object to be used for context.}
 
 \item{obj}{A basic list (from \code{contents_record()}) to be replayed.}
 
@@ -48,7 +48,7 @@ turn <- Turn("user")
 turn
 #> <Turn: user>
 
-# Get the turn record
+# Get the turn's record
 # Note: Removes all S7 class instances
 turn_recorded <- contents_record(turn, chat = chat)
 str(turn_recorded)

From 222738290807d350b9c8b8d63e7bd14d1da98aaa Mon Sep 17 00:00:00 2001
From: Barret Schloerke <barret@posit.co>
Date: Tue, 20 May 2025 14:17:34 -0400
Subject: [PATCH 23/34] bump version

---
 DESCRIPTION | 2 +-
 1 file changed, 1 insertion(+), 1 deletion(-)

diff --git a/DESCRIPTION b/DESCRIPTION
index 0c658a98..5d607fac 100644
--- a/DESCRIPTION
+++ b/DESCRIPTION
@@ -1,6 +1,6 @@
 Package: ellmer
 Title: Chat with Large Language Models
-Version: 0.2.0.9000
+Version: 0.2.0.9001
 Authors@R: c(
     person("Hadley", "Wickham", , "hadley@posit.co", role = c("aut", "cre"),
            comment = c(ORCID = "0000-0003-4757-117X")),

From a011e7bb24bf39bd59041313be41c832e6aa6860 Mon Sep 17 00:00:00 2001
From: Barret Schloerke <barret@posit.co>
Date: Wed, 21 May 2025 12:19:18 -0400
Subject: [PATCH 24/34] Loop over list elements when recording or replaying

---
 R/content-replay.R                   | 276 ++++++++++++++++++---------
 man/contents_record.Rd               |   6 +-
 tests/testthat/test-content-replay.R |  13 ++
 3 files changed, 199 insertions(+), 96 deletions(-)

diff --git a/R/content-replay.R b/R/content-replay.R
index 10e61cd6..1056e32a 100644
--- a/R/content-replay.R
+++ b/R/content-replay.R
@@ -70,16 +70,25 @@ contents_record <-
         )
       }
 
+      if (
+        is_list_of_s7_objects(content)
+        # (is_unnamed_list(content) || is_named_list(content)) &&
+        # all(map_lgl(content, S7_inherits))
+      ) {
+        # If the content is a list, we need to record each element
+        # and return a list of the recorded elements
+        return(lapply(content, contents_record, chat = chat))
+      }
+
       recorded <- S7::S7_dispatch()
 
-      for (name in c("version", "class", "props")) {
-        if (!name %in% names(recorded)) {
-          cli::cli_abort(
-            "Expected the recorded object to have a {.val {name}} property.",
-            call = caller_env()
-          )
-        }
+      if (!is_recorded_object(recorded)) {
+        cli::cli_abort(
+          "Expected the recorded object to be a list with at least names 'version', 'class', and 'props'.",
+          call = caller_env()
+        )
       }
+
       if (
         !is.character(recorded$class) ||
           length(recorded$class) != 1
@@ -93,46 +102,81 @@ contents_record <-
       recorded
     }
   )
+
+prop_is_read_only <- function(prop) {
+  is.function(prop$getter) && !is.function(prop$setter)
+}
+prop_type_is_func <- function(prop) {
+  all(class(prop) == class(S7::S7_function)) &&
+    prop$class == S7::S7_function$class
+}
 method(contents_record, S7::S7_object) <- function(content, ..., chat) {
-  prop_names <- S7::prop_names(content)
+  # Remove read-only properties
+  cls_props <- S7::S7_class(content)@properties
+  prop_names <- names(cls_props)[!map_lgl(cls_props, prop_is_read_only)]
+
   class_name <- class(content)[1]
-  list(
-    version = 1,
-    class = class(content)[1],
-    props = setNames(
-      lapply(prop_names, function(prop_name) {
-        prop_value <- S7::prop(prop_name, object = content)
-        if (S7_inherits(prop_value)) {
-          contents_record(prop_value, chat = chat)
-        } else {
-          prop_value
-        }
-      }),
-      prop_names
-    )
+
+  recorded_props <- setNames(
+    lapply(prop_names, function(prop_name) {
+      prop_value <- S7::prop(prop_name, object = content)
+      if (S7_inherits(prop_value)) {
+        # Recursive call to S7 object
+        contents_record(prop_value, chat = chat)
+      } else if (
+        is_list_of_s7_objects(prop_value)
+        # (is_unnamed_list(prop_value) || is_named_list(prop_value)) &&
+        #   all(map_lgl(prop_value, S7_inherits))
+      ) {
+        # Make record of each item in prop.
+        # Do not recurse forever!
+        lapply(prop_value, contents_record, chat = chat)
+      } else {
+        prop_value
+      }
+    }),
+    prop_names
   )
-}
-method(contents_record, Turn) <- function(content, ..., chat) {
+
+  # Remove non-serializable properties
+  recorded_props <- Filter(
+    function(x) {
+      !is.function(x)
+    },
+    recorded_props
+  )
+
   list(
     version = 1,
-    class = class(content)[1],
-    props = list(
-      role = content@role,
-      contents = lapply(content@contents, contents_record, chat = chat),
-      json = content@json,
-      tokens = content@tokens
-      # text = getter only!
-    )
+    class = class_name,
+    props = recorded_props
   )
 }
 
+
+# method(contents_record, Turn) <- function(content, ..., chat) {
+#   ret <- contents_record(super(content, S7::S7_object), chat = chat)
+#   ret$props$text <- NULL
+#   ret
+#   # list(
+#   #   version = 1,
+#   #   class = class(content)[1],
+#   #   props = list(
+#   #     role = content@role,
+#   #     contents = lapply(content@contents, contents_record, chat = chat),
+#   #     json = content@json,
+#   #     tokens = content@tokens
+#   #     # text = getter only!
+#   #   )
+#   # )
+# }
+
 #' @rdname contents_record
 #' @export
 # Holy "Holy Trait" dispatching, Batman!
 contents_replay <- function(
   obj,
   ...,
-  cls = NULL,
   chat,
   env = rlang::caller_env()
 ) {
@@ -150,10 +194,30 @@ contents_replay <- function(
   if (!is.list(obj)) {
     return(obj)
   }
-  if (!all(c("version", "class", "props") %in% names(obj))) {
+
+  if (!is_recorded_object(obj)) {
+    if (
+      is_list_of_recorded_objects(obj)
+      # (is_named_list(obj) || is_unnamed_list(obj)) &&
+      #   all(map_lgl(obj, is_recorded_object))
+    ) {
+      # If the object is a list, we need to replay each element
+      # and return a list of the replayed elements
+      return(lapply(obj, contents_replay, chat = chat, env = env))
+    }
     return(obj)
   }
 
+  # if (!all(c("version", "class", "props") %in% names(obj))) {
+  #   # If the object isn't a recorded object, return it as is
+  #   if (is_named_list(obj)) {
+  #     # If the object is a named list, we need to replay each element
+  #     # and return a list of the replayed elements
+  #     return(lapply(obj, contents_replay, chat = chat, env = env))
+  #   }
+  #   return(obj)
+  # }
+
   class_value <- obj$class
   if (!(is.character(class_value) && length(class_value) > 0)) {
     return(obj)
@@ -232,23 +296,26 @@ method(contents_replay_class, S7::S7_object) <- function(
 }
 
 
-method(contents_record, ToolDef) <- function(content, ..., chat) {
-  list(
-    version = 1,
-    class = class(content)[1],
-    props = list(
-      name = content@name,
-      # Do not record the function!
-      # It is not serializable and will not be neeeded after replay as the _real_ tool would be leveraged.
-      # However, keep all the other properties as the metadata could be useful.
-      fun = NULL,
-      description = content@description,
-      arguments = contents_record(content@arguments, chat = chat),
-      convert = content@convert,
-      annotations = content@annotations
-    )
-  )
-}
+# method(contents_record, ToolDef) <- function(content, ..., chat) {
+#   ret <- contents_record(super(content, S7::S7_object), chat = chat)
+#   # Do not record the function!
+#   # It is not serializable and will not be neeeded after replay as the _real_ tool would be leveraged.
+#   # However, keep all the other properties as the metadata could be useful.
+#   ret$props$fun <- NULL
+#   ret
+#   # list(
+#   #   version = 1,
+#   #   class = class(content)[1],
+#   #   props = list(
+#   #     name = content@name,
+#   #     fun = NULL,
+#   #     description = content@description,
+#   #     arguments = contents_record(content@arguments, chat = chat),
+#   #     convert = content@convert,
+#   #     annotations = content@annotations
+#   #   )
+#   # )
+# }
 method(contents_replay_class, ToolDef) <- function(
   cls,
   obj,
@@ -282,48 +349,47 @@ method(contents_replay_class, ToolDef) <- function(
 }
 
 
-method(contents_record, TypeObject) <- function(content, ..., chat) {
-  list(
-    version = 1,
-    class = class(content)[1],
-    props = list(
-      description = content@description,
-      required = content@required,
-      properties = lapply(
-        content@properties,
-        contents_record,
-        chat = chat
-      ),
-      additional_properties = content@additional_properties
-    )
-  )
-}
-method(contents_replay_class, TypeObject) <- function(
-  cls,
-  obj,
-  ...,
-  chat,
-  env = rlang::caller_env()
-) {
-  if (obj$version != 1) {
-    cli::cli_abort(
-      "Unsupported version {.val {obj$version}}.",
-      call = caller_env()
-    )
-  }
-
-  TypeObject(
-    description = obj$props$description,
-    required = obj$props$required,
-    properties = lapply(
-      obj$props$properties,
-      contents_replay,
-      chat = chat
-    ),
-    additional_properties = obj$props$additional_properties
-  )
-}
-
+# method(contents_record, TypeObject) <- function(content, ..., chat) {
+#   list(
+#     version = 1,
+#     class = class(content)[1],
+#     props = list(
+#       description = content@description,
+#       required = content@required,
+#       properties = lapply(
+#         content@properties,
+#         contents_record,
+#         chat = chat
+#       ),
+#       additional_properties = content@additional_properties
+#     )
+#   )
+# }
+# method(contents_replay_class, TypeObject) <- function(
+#   cls,
+#   obj,
+#   ...,
+#   chat,
+#   env = rlang::caller_env()
+# ) {
+#   if (obj$version != 1) {
+#     cli::cli_abort(
+#       "Unsupported version {.val {obj$version}}.",
+#       call = caller_env()
+#     )
+#   }
+
+#   TypeObject(
+#     description = obj$props$description,
+#     required = obj$props$required,
+#     properties = lapply(
+#       obj$props$properties,
+#       contents_replay,
+#       chat = chat
+#     ),
+#     additional_properties = obj$props$additional_properties
+#   )
+# }
 
 #' Retrieve the class constructor
 #'
@@ -362,3 +428,27 @@ get_cls_constructor <- function(class_value, ..., env = rlang::caller_env()) {
     )
   }
 }
+
+# is_unnamed_list <- function(x) {
+#   is.list(x) &&
+#     (all(!rlang::have_name(x)))
+# }
+
+# is_named_list <- function(x) {
+#   is.list(x) &&
+#     (all(rlang::have_name(x)))
+# }
+is_recorded_object <- function(x) {
+  is.list(x) &&
+    all(c("version", "class", "props") %in% names(x))
+}
+
+is_list_of_s7_objects <- function(x) {
+  is.list(x) &&
+    all(map_lgl(x, S7_inherits))
+}
+
+is_list_of_recorded_objects <- function(x) {
+  is.list(x) &&
+    all(map_lgl(x, is_recorded_object))
+}
diff --git a/man/contents_record.Rd b/man/contents_record.Rd
index 99d4deb5..9cfda56c 100644
--- a/man/contents_record.Rd
+++ b/man/contents_record.Rd
@@ -8,7 +8,7 @@
 \usage{
 contents_record(content, ..., chat)
 
-contents_replay(obj, ..., cls = NULL, chat, env = rlang::caller_env())
+contents_replay(obj, ..., chat, env = rlang::caller_env())
 
 contents_replay_class(cls, obj, ..., chat, env = rlang::caller_env())
 }
@@ -21,9 +21,9 @@ contents_replay_class(cls, obj, ..., chat, env = rlang::caller_env())
 
 \item{obj}{A basic list (from \code{contents_record()}) to be replayed.}
 
-\item{cls}{The class constructor to be used for replaying the object.}
-
 \item{env}{The environment to find non-package classes.}
+
+\item{cls}{The class constructor to be used for replaying the object.}
 }
 \description{
 These generic functions can be use to convert \link{Turn} contents or \link{Content}
diff --git a/tests/testthat/test-content-replay.R b/tests/testthat/test-content-replay.R
index a19496ae..5f01b380 100644
--- a/tests/testthat/test-content-replay.R
+++ b/tests/testthat/test-content-replay.R
@@ -1,5 +1,18 @@
 # -------------------------------------------------------------------------
 
+test_that("can round trip of Turn record/replay", {
+  test_record_replay(Turn("user"))
+
+  test_record_replay(Turn(
+    "user",
+    list(
+      ContentText("hello world"),
+      ContentText("hello world2")
+    )
+  ))
+})
+
+
 test_that("can round trip of Content record/replay", {
   test_record_replay(Content())
 })

From 4493487f4e06bac6079eafe88ace2bef52ace3b9 Mon Sep 17 00:00:00 2001
From: Barret Schloerke <barret@posit.co>
Date: Wed, 21 May 2025 12:45:04 -0400
Subject: [PATCH 25/34] clean up code and add test for unknown tool

---
 R/content-replay.R                   | 154 +++------------------------
 tests/testthat/test-content-replay.R |  29 ++++-
 2 files changed, 44 insertions(+), 139 deletions(-)

diff --git a/R/content-replay.R b/R/content-replay.R
index 1056e32a..082fc844 100644
--- a/R/content-replay.R
+++ b/R/content-replay.R
@@ -70,11 +70,7 @@ contents_record <-
         )
       }
 
-      if (
-        is_list_of_s7_objects(content)
-        # (is_unnamed_list(content) || is_named_list(content)) &&
-        # all(map_lgl(content, S7_inherits))
-      ) {
+      if (is_list_of_s7_objects(content)) {
         # If the content is a list, we need to record each element
         # and return a list of the recorded elements
         return(lapply(content, contents_record, chat = chat))
@@ -103,31 +99,20 @@ contents_record <-
     }
   )
 
-prop_is_read_only <- function(prop) {
-  is.function(prop$getter) && !is.function(prop$setter)
-}
-prop_type_is_func <- function(prop) {
-  all(class(prop) == class(S7::S7_function)) &&
-    prop$class == S7::S7_function$class
-}
 method(contents_record, S7::S7_object) <- function(content, ..., chat) {
-  # Remove read-only properties
+  class_name <- class(content)[1]
+
+  # Remove read-only props
   cls_props <- S7::S7_class(content)@properties
   prop_names <- names(cls_props)[!map_lgl(cls_props, prop_is_read_only)]
 
-  class_name <- class(content)[1]
-
   recorded_props <- setNames(
     lapply(prop_names, function(prop_name) {
       prop_value <- S7::prop(prop_name, object = content)
       if (S7_inherits(prop_value)) {
         # Recursive call to S7 object
         contents_record(prop_value, chat = chat)
-      } else if (
-        is_list_of_s7_objects(prop_value)
-        # (is_unnamed_list(prop_value) || is_named_list(prop_value)) &&
-        #   all(map_lgl(prop_value, S7_inherits))
-      ) {
+      } else if (is_list_of_s7_objects(prop_value)) {
         # Make record of each item in prop.
         # Do not recurse forever!
         lapply(prop_value, contents_record, chat = chat)
@@ -154,23 +139,6 @@ method(contents_record, S7::S7_object) <- function(content, ..., chat) {
 }
 
 
-# method(contents_record, Turn) <- function(content, ..., chat) {
-#   ret <- contents_record(super(content, S7::S7_object), chat = chat)
-#   ret$props$text <- NULL
-#   ret
-#   # list(
-#   #   version = 1,
-#   #   class = class(content)[1],
-#   #   props = list(
-#   #     role = content@role,
-#   #     contents = lapply(content@contents, contents_record, chat = chat),
-#   #     json = content@json,
-#   #     tokens = content@tokens
-#   #     # text = getter only!
-#   #   )
-#   # )
-# }
-
 #' @rdname contents_record
 #' @export
 # Holy "Holy Trait" dispatching, Batman!
@@ -196,28 +164,12 @@ contents_replay <- function(
   }
 
   if (!is_recorded_object(obj)) {
-    if (
-      is_list_of_recorded_objects(obj)
-      # (is_named_list(obj) || is_unnamed_list(obj)) &&
-      #   all(map_lgl(obj, is_recorded_object))
-    ) {
-      # If the object is a list, we need to replay each element
-      # and return a list of the replayed elements
+    if (is_list_of_recorded_objects(obj)) {
       return(lapply(obj, contents_replay, chat = chat, env = env))
     }
     return(obj)
   }
 
-  # if (!all(c("version", "class", "props") %in% names(obj))) {
-  #   # If the object isn't a recorded object, return it as is
-  #   if (is_named_list(obj)) {
-  #     # If the object is a named list, we need to replay each element
-  #     # and return a list of the replayed elements
-  #     return(lapply(obj, contents_replay, chat = chat, env = env))
-  #   }
-  #   return(obj)
-  # }
-
   class_value <- obj$class
   if (!(is.character(class_value) && length(class_value) > 0)) {
     return(obj)
@@ -288,34 +240,10 @@ method(contents_replay_class, S7::S7_object) <- function(
 
   # While this seems like a bit of extra work, the tracebacks are accurate
   # vs referencing an unrelated parameter name in the traceback
-  rlang::exec(
-    cls_name,
-    !!!obj_props,
-    .env = env
-  )
+  rlang::exec(cls_name, !!!obj_props, .env = env)
 }
 
 
-# method(contents_record, ToolDef) <- function(content, ..., chat) {
-#   ret <- contents_record(super(content, S7::S7_object), chat = chat)
-#   # Do not record the function!
-#   # It is not serializable and will not be neeeded after replay as the _real_ tool would be leveraged.
-#   # However, keep all the other properties as the metadata could be useful.
-#   ret$props$fun <- NULL
-#   ret
-#   # list(
-#   #   version = 1,
-#   #   class = class(content)[1],
-#   #   props = list(
-#   #     name = content@name,
-#   #     fun = NULL,
-#   #     description = content@description,
-#   #     arguments = contents_record(content@arguments, chat = chat),
-#   #     convert = content@convert,
-#   #     annotations = content@annotations
-#   #   )
-#   # )
-# }
 method(contents_replay_class, ToolDef) <- function(
   cls,
   obj,
@@ -337,60 +265,17 @@ method(contents_replay_class, ToolDef) <- function(
     return(matched_tool)
   }
 
-  # If no tool is found, return placeholder tool
-  ToolDef(
-    name = obj$props$name,
-    # fun = NULL, # fun was not serialized
-    description = obj$props$description,
-    arguments = contents_replay(obj$props$arguments, chat = chat),
-    convert = obj$props$convert,
-    annotations = obj$props$annotations
+  # If no tool is found, return placeholder tool containing the metadata
+  ret <- contents_replay_class(
+    super(cls, S7::S7_object),
+    obj,
+    chat = chat,
+    env = env
   )
+  ret
 }
 
 
-# method(contents_record, TypeObject) <- function(content, ..., chat) {
-#   list(
-#     version = 1,
-#     class = class(content)[1],
-#     props = list(
-#       description = content@description,
-#       required = content@required,
-#       properties = lapply(
-#         content@properties,
-#         contents_record,
-#         chat = chat
-#       ),
-#       additional_properties = content@additional_properties
-#     )
-#   )
-# }
-# method(contents_replay_class, TypeObject) <- function(
-#   cls,
-#   obj,
-#   ...,
-#   chat,
-#   env = rlang::caller_env()
-# ) {
-#   if (obj$version != 1) {
-#     cli::cli_abort(
-#       "Unsupported version {.val {obj$version}}.",
-#       call = caller_env()
-#     )
-#   }
-
-#   TypeObject(
-#     description = obj$props$description,
-#     required = obj$props$required,
-#     properties = lapply(
-#       obj$props$properties,
-#       contents_replay,
-#       chat = chat
-#     ),
-#     additional_properties = obj$props$additional_properties
-#   )
-# }
-
 #' Retrieve the class constructor
 #'
 #' @description
@@ -429,15 +314,10 @@ get_cls_constructor <- function(class_value, ..., env = rlang::caller_env()) {
   }
 }
 
-# is_unnamed_list <- function(x) {
-#   is.list(x) &&
-#     (all(!rlang::have_name(x)))
-# }
+prop_is_read_only <- function(prop) {
+  is.function(prop$getter) && !is.function(prop$setter)
+}
 
-# is_named_list <- function(x) {
-#   is.list(x) &&
-#     (all(rlang::have_name(x)))
-# }
 is_recorded_object <- function(x) {
   is.list(x) &&
     all(c("version", "class", "props") %in% names(x))
diff --git a/tests/testthat/test-content-replay.R b/tests/testthat/test-content-replay.R
index 5f01b380..b86c844f 100644
--- a/tests/testthat/test-content-replay.R
+++ b/tests/testthat/test-content-replay.R
@@ -66,7 +66,7 @@ test_that("can round trip of ContentThinking record/replay", {
 test_that("can round trip of ContentTool record/replay", {
   chat <- chat_ollama_test("Be as terse as possible; no punctuation")
   tool_rnorm <- tool(
-    stats::rnorm,
+    rnorm,
     "Drawn numbers from a random normal distribution",
     n = type_integer("The number of observations. Must be a positive integer."),
     mean = type_number("The mean value of the distribution."),
@@ -85,7 +85,8 @@ test_that("can round trip of ContentTool record/replay", {
 test_that("can round trip of ToolDef record/replay", {
   chat <- chat_ollama_test("Be as terse as possible; no punctuation")
   tool_rnorm <- tool(
-    stats::rnorm,
+    # Use `rnorm` to avoid loading the package... this causes the name to not be auto found
+    rnorm,
     "Drawn numbers from a random normal distribution",
     n = type_integer("The number of observations. Must be a positive integer."),
     mean = type_number("The mean value of the distribution."),
@@ -106,6 +107,30 @@ test_that("can round trip of ToolDef record/replay", {
     ),
     chat = chat
   )
+
+  recorded_tool <- contents_record(tool_rnorm, chat = chat)
+  chat_empty <- chat_ollama_test("Be as terse as possible; no punctuation")
+  replayed_tool <- contents_replay(recorded_tool, chat = chat_empty)
+
+  tool_rnorm_empty <- ToolDef(
+    # rnorm,
+    name = "rnorm",
+    description = "Drawn numbers from a random normal distribution",
+    arguments = type_object(
+      n = type_integer(
+        "The number of observations. Must be a positive integer."
+      ),
+      mean = type_number("The mean value of the distribution."),
+      sd = type_number(
+        "The standard deviation of the distribution. Must be a non-negative number."
+      )
+    ),
+  )
+
+  expect_equal(
+    replayed_tool,
+    tool_rnorm_empty
+  )
 })
 
 test_that("can round trip of ContentToolResult record/replay", {

From 4a80ad064fe9639d0f3844102bc5ed58851d6f28 Mon Sep 17 00:00:00 2001
From: Hadley Wickham <h.wickham@gmail.com>
Date: Mon, 9 Jun 2025 10:34:58 -0700
Subject: [PATCH 26/34] Switch tests to use chatgpt

---
 tests/testthat/helper-content-replay.R |  2 +-
 tests/testthat/test-content-replay.R   | 14 +++++++-------
 2 files changed, 8 insertions(+), 8 deletions(-)

diff --git a/tests/testthat/helper-content-replay.R b/tests/testthat/helper-content-replay.R
index feaa1040..9f7acfb9 100644
--- a/tests/testthat/helper-content-replay.R
+++ b/tests/testthat/helper-content-replay.R
@@ -1,7 +1,7 @@
 test_record_replay <- function(
   x,
   ...,
-  chat = chat_ollama_test("Be as terse as possible; no punctuation"),
+  chat = chat_openai_test(),
   env = rlang::caller_env()
 ) {
   rlang::check_dots_empty()
diff --git a/tests/testthat/test-content-replay.R b/tests/testthat/test-content-replay.R
index b86c844f..61874a46 100644
--- a/tests/testthat/test-content-replay.R
+++ b/tests/testthat/test-content-replay.R
@@ -64,7 +64,7 @@ test_that("can round trip of ContentThinking record/replay", {
 })
 
 test_that("can round trip of ContentTool record/replay", {
-  chat <- chat_ollama_test("Be as terse as possible; no punctuation")
+  chat <- chat_openai_test()
   tool_rnorm <- tool(
     rnorm,
     "Drawn numbers from a random normal distribution",
@@ -83,7 +83,7 @@ test_that("can round trip of ContentTool record/replay", {
 })
 
 test_that("can round trip of ToolDef record/replay", {
-  chat <- chat_ollama_test("Be as terse as possible; no punctuation")
+  chat <- chat_openai_test()
   tool_rnorm <- tool(
     # Use `rnorm` to avoid loading the package... this causes the name to not be auto found
     rnorm,
@@ -109,7 +109,7 @@ test_that("can round trip of ToolDef record/replay", {
   )
 
   recorded_tool <- contents_record(tool_rnorm, chat = chat)
-  chat_empty <- chat_ollama_test("Be as terse as possible; no punctuation")
+  chat_empty <- chat_openai_test()
   replayed_tool <- contents_replay(recorded_tool, chat = chat_empty)
 
   tool_rnorm_empty <- ToolDef(
@@ -143,7 +143,7 @@ test_that("can round trip of ContentToolResult record/replay", {
     )
   )
 
-  chat <- chat_ollama_test("Be as terse as possible; no punctuation")
+  chat <- chat_openai_test()
   tool_rnorm <- tool(
     stats::rnorm,
     "Drawn numbers from a random normal distribution",
@@ -191,7 +191,7 @@ test_that("can round trip of ContentPDF record/replay", {
 })
 
 test_that("non-package classes are recorded/replayed by default", {
-  chat <- chat_ollama_test("Be as terse as possible; no punctuation")
+  chat <- chat_openai_test()
 
   LocalClass <- S7::new_class(
     "LocalClass",
@@ -208,7 +208,7 @@ test_that("non-package classes are recorded/replayed by default", {
 
 
 test_that("unknown classes cause errors", {
-  chat <- chat_ollama_test("Be as terse as possible; no punctuation")
+  chat <- chat_openai_test()
   recorded <- contents_record(Turn("user"), chat = chat)
   recorded$class <- "ellmer::Turn2"
 
@@ -232,7 +232,7 @@ test_that("replay classes are S7 classes", {
     OtherName(name = name)
   }
 
-  chat <- chat_ollama_test("Be as terse as possible; no punctuation")
+  chat <- chat_openai_test()
   recorded <- contents_record(LocalClass("testname"), chat = chat)
   expect_error(
     contents_replay(recorded, chat = chat),

From 6feb5410071c9538a82e2902d7bf0a10b119cb3c Mon Sep 17 00:00:00 2001
From: Hadley Wickham <h.wickham@gmail.com>
Date: Mon, 9 Jun 2025 10:39:04 -0700
Subject: [PATCH 27/34] Tweak docs/style; unexport `contents_replay_class`

---
 NAMESPACE              |  1 -
 R/content-replay.R     | 89 ++++++++++--------------------------------
 man/contents_record.Rd | 55 ++++++++------------------
 3 files changed, 37 insertions(+), 108 deletions(-)

diff --git a/NAMESPACE b/NAMESPACE
index 20dc6424..d4b4b1ec 100644
--- a/NAMESPACE
+++ b/NAMESPACE
@@ -58,7 +58,6 @@ export(contents_html)
 export(contents_markdown)
 export(contents_record)
 export(contents_replay)
-export(contents_replay_class)
 export(contents_text)
 export(create_tool_def)
 export(google_upload)
diff --git a/R/content-replay.R b/R/content-replay.R
index 082fc844..42ae30f2 100644
--- a/R/content-replay.R
+++ b/R/content-replay.R
@@ -8,54 +8,32 @@ NULL
 #' Save and restore content
 #'
 #' @description
-#' These generic functions can be use to convert [Turn] contents or [Content]
-#' objects into easily serializable representations.
+#' These generic functions can be use to convert [Turn]/[Content] objects
+#' into easily serializable representations.
 #'
-#' * `contents_record()` will accept a [Turn] or [Content] related objects and return a
-#'   basic list that can be easily serialized.
-#' * `contents_replay()` will accept a basic list (from `contents_record()`) and
-#'   return a corresponding [Turn] or [Content] related object.
-#' * `contents_replay_class()` is a generic function that is dispatched from
-#'   within `contents_replay()`. `contents_replay()` will retrieve the
-#'   corresponding contructor class from within the basic list information and
-#'   use the class for dispatching.
+#' * `contents_record()` will accept a [Turn] or [Content] and return a
+#'   simple list.
+#' * `contents_replay()` will accept a simple list (from `contents_record()`)
+#'   and return a [Turn] or [Content] object.
 #'
-#' Note, all S7 classes should have the same class name as the variable name. Ex: `FooBar <- new_class("FooBar")`, not `OtherName <- new_class("FooBar")`. This is a requirement for when replaying the object.
-#'
-#' @param content A [Turn] or [Content] object to have its record retrieved.
-#' @param obj A basic list (from `contents_record()`) to be replayed.
+#' @param content A [Turn] or [Content] object to serialize.
+#' @param obj A basic list to desierialize.
 #' @param cls The class constructor to be used for replaying the object.
 #' @param chat A [Chat] object to be used for context.
 #' @param env The environment to find non-package classes.
 #' @param ... Not used.
 #'
-#' @examples
-#' \dontrun{
-#' chat <- chat_ollama(model = "llama3.2")
-#' turn <- Turn("user")
-#' turn
-#' #> <Turn: user>
+#' @examplesIf has_credentials("openai")
+#' chat <- chat_openai(model = "gpt-4.1-nano")
+#' chat$chat("Where is the capital of France?")
 #'
-#' # Get the turn's record
-#' # Note: Removes all S7 class instances
-#' turn_recorded <- contents_record(turn, chat = chat)
+#' # Serialize to a simple list
+#' turn_recorded <- contents_record(chat$get_turns(), chat = chat)
 #' str(turn_recorded)
-#' #> List of 3
-#' #>  $ version: num 1
-#' #>  $ class  : chr "ellmer::Turn"
-#' #>  $ props  :List of 4
-#' #>   ..$ role    : chr "user"
-#' #>   ..$ contents: list()
-#' #>   ..$ json    : list()
-#' #>   ..$ tokens  : num [1:2] 0 0
 #'
-#' # Restore the turn from the record
-#' # Note: This will not restore the _original_ object,
-#' # but a new object with the same properties
+#' # Deserialize back to S7 objects
 #' turn_replayed <- contents_replay(turn_recorded, chat = chat)
 #' turn_replayed
-#' #> <Turn: user>
-#' }
 #' @export
 #' @rdname contents_record
 contents_record <-
@@ -63,12 +41,7 @@ contents_record <-
     "contents_record",
     "content",
     function(content, ..., chat) {
-      if (!(R6::is.R6(chat) && inherits(chat, "Chat"))) {
-        cli::cli_abort(
-          "Expected a Chat object at `chat=`, but received {.val {chat}}.",
-          call = caller_env()
-        )
-      }
+      check_chat(chat, call = caller_env())
 
       if (is_list_of_s7_objects(content)) {
         # If the content is a list, we need to record each element
@@ -124,12 +97,7 @@ method(contents_record, S7::S7_object) <- function(content, ..., chat) {
   )
 
   # Remove non-serializable properties
-  recorded_props <- Filter(
-    function(x) {
-      !is.function(x)
-    },
-    recorded_props
-  )
+  recorded_props <- Filter(function(x) !is.function(x), recorded_props)
 
   list(
     version = 1,
@@ -142,18 +110,8 @@ method(contents_record, S7::S7_object) <- function(content, ..., chat) {
 #' @rdname contents_record
 #' @export
 # Holy "Holy Trait" dispatching, Batman!
-contents_replay <- function(
-  obj,
-  ...,
-  chat,
-  env = rlang::caller_env()
-) {
-  if (!(R6::is.R6(chat) && inherits(chat, "Chat"))) {
-    cli::cli_abort(
-      "Expected a Chat object at `chat=`, but received {.val {chat}}.",
-      call = caller_env()
-    )
-  }
+contents_replay <- function(obj, ..., chat, env = caller_env()) {
+  check_chat(chat, call = caller_env())
 
   # Find any reason to not believe `obj` is a recorded object.
   # If not a recorded object, return it as is.
@@ -199,8 +157,6 @@ contents_replay <- function(
   handler(cls, obj, chat = chat, env = env)
 }
 
-#' @rdname contents_record
-#' @export
 contents_replay_class <- new_generic(
   "contents_replay_class",
   "cls",
@@ -319,16 +275,13 @@ prop_is_read_only <- function(prop) {
 }
 
 is_recorded_object <- function(x) {
-  is.list(x) &&
-    all(c("version", "class", "props") %in% names(x))
+  is.list(x) && all(c("version", "class", "props") %in% names(x))
 }
 
 is_list_of_s7_objects <- function(x) {
-  is.list(x) &&
-    all(map_lgl(x, S7_inherits))
+  is.list(x) && all(map_lgl(x, S7_inherits))
 }
 
 is_list_of_recorded_objects <- function(x) {
-  is.list(x) &&
-    all(map_lgl(x, is_recorded_object))
+  is.list(x) && all(map_lgl(x, is_recorded_object))
 }
diff --git a/man/contents_record.Rd b/man/contents_record.Rd
index 9cfda56c..d1218de2 100644
--- a/man/contents_record.Rd
+++ b/man/contents_record.Rd
@@ -3,69 +3,46 @@
 \name{contents_record}
 \alias{contents_record}
 \alias{contents_replay}
-\alias{contents_replay_class}
 \title{Save and restore content}
 \usage{
 contents_record(content, ..., chat)
 
-contents_replay(obj, ..., chat, env = rlang::caller_env())
-
-contents_replay_class(cls, obj, ..., chat, env = rlang::caller_env())
+contents_replay(obj, ..., chat, env = caller_env())
 }
 \arguments{
-\item{content}{A \link{Turn} or \link{Content} object to have its record retrieved.}
+\item{content}{A \link{Turn} or \link{Content} object to serialize.}
 
 \item{...}{Not used.}
 
 \item{chat}{A \link{Chat} object to be used for context.}
 
-\item{obj}{A basic list (from \code{contents_record()}) to be replayed.}
+\item{obj}{A basic list to desierialize.}
 
 \item{env}{The environment to find non-package classes.}
 
 \item{cls}{The class constructor to be used for replaying the object.}
 }
 \description{
-These generic functions can be use to convert \link{Turn} contents or \link{Content}
-objects into easily serializable representations.
+These generic functions can be use to convert \link{Turn}/\link{Content} objects
+into easily serializable representations.
 \itemize{
-\item \code{contents_record()} will accept a \link{Turn} or \link{Content} related objects and return a
-basic list that can be easily serialized.
-\item \code{contents_replay()} will accept a basic list (from \code{contents_record()}) and
-return a corresponding \link{Turn} or \link{Content} related object.
-\item \code{contents_replay_class()} is a generic function that is dispatched from
-within \code{contents_replay()}. \code{contents_replay()} will retrieve the
-corresponding contructor class from within the basic list information and
-use the class for dispatching.
+\item \code{contents_record()} will accept a \link{Turn} or \link{Content} and return a
+simple list.
+\item \code{contents_replay()} will accept a simple list (from \code{contents_record()})
+and return a \link{Turn} or \link{Content} object.
 }
-
-Note, all S7 classes should have the same class name as the variable name. Ex: \code{FooBar <- new_class("FooBar")}, not \code{OtherName <- new_class("FooBar")}. This is a requirement for when replaying the object.
 }
 \examples{
-\dontrun{
-chat <- chat_ollama(model = "llama3.2")
-turn <- Turn("user")
-turn
-#> <Turn: user>
+\dontshow{if (has_credentials("openai")) (if (getRversion() >= "3.4") withAutoprint else force)(\{ # examplesIf}
+chat <- chat_openai(model = "gpt-4.1-nano")
+chat$chat("Where is the capital of France?")
 
-# Get the turn's record
-# Note: Removes all S7 class instances
-turn_recorded <- contents_record(turn, chat = chat)
+# Serialize to a simple list
+turn_recorded <- contents_record(chat$get_turns(), chat = chat)
 str(turn_recorded)
-#> List of 3
-#>  $ version: num 1
-#>  $ class  : chr "ellmer::Turn"
-#>  $ props  :List of 4
-#>   ..$ role    : chr "user"
-#>   ..$ contents: list()
-#>   ..$ json    : list()
-#>   ..$ tokens  : num [1:2] 0 0
 
-# Restore the turn from the record
-# Note: This will not restore the _original_ object,
-# but a new object with the same properties
+# Deserialize back to S7 objects
 turn_replayed <- contents_replay(turn_recorded, chat = chat)
 turn_replayed
-#> <Turn: user>
-}
+\dontshow{\}) # examplesIf}
 }

From 20b961ec20f25f8c46980ed48bc8cd3f3fadb7fa Mon Sep 17 00:00:00 2001
From: Barret Schloerke <barret@posit.co>
Date: Mon, 9 Jun 2025 14:00:11 -0400
Subject: [PATCH 28/34] doc update

Co-Authored-By: Hadley Wickham <hadley@posit.co>
---
 R/content-replay.R     | 3 +--
 man/contents_record.Rd | 3 +--
 2 files changed, 2 insertions(+), 4 deletions(-)

diff --git a/R/content-replay.R b/R/content-replay.R
index 42ae30f2..ef3d1848 100644
--- a/R/content-replay.R
+++ b/R/content-replay.R
@@ -11,8 +11,7 @@ NULL
 #' These generic functions can be use to convert [Turn]/[Content] objects
 #' into easily serializable representations.
 #'
-#' * `contents_record()` will accept a [Turn] or [Content] and return a
-#'   simple list.
+#' * `contents_record()` accept a [Turn] or [Content] and return a simple list.
 #' * `contents_replay()` will accept a simple list (from `contents_record()`)
 #'   and return a [Turn] or [Content] object.
 #'
diff --git a/man/contents_record.Rd b/man/contents_record.Rd
index d1218de2..f38a615e 100644
--- a/man/contents_record.Rd
+++ b/man/contents_record.Rd
@@ -26,8 +26,7 @@ contents_replay(obj, ..., chat, env = caller_env())
 These generic functions can be use to convert \link{Turn}/\link{Content} objects
 into easily serializable representations.
 \itemize{
-\item \code{contents_record()} will accept a \link{Turn} or \link{Content} and return a
-simple list.
+\item \code{contents_record()} accept a \link{Turn} or \link{Content} and return a simple list.
 \item \code{contents_replay()} will accept a simple list (from \code{contents_record()})
 and return a \link{Turn} or \link{Content} object.
 }

From f41cc3c2552839186ce4872ce196b264357e2702 Mon Sep 17 00:00:00 2001
From: Barret Schloerke <barret@posit.co>
Date: Mon, 9 Jun 2025 14:03:46 -0400
Subject: [PATCH 29/34] Remove prefix of `rlang::`

---
 R/content-replay.R | 22 +++++++++++-----------
 R/tools-def.R      |  2 +-
 2 files changed, 12 insertions(+), 12 deletions(-)

diff --git a/R/content-replay.R b/R/content-replay.R
index ef3d1848..b0f3788a 100644
--- a/R/content-replay.R
+++ b/R/content-replay.R
@@ -159,7 +159,7 @@ contents_replay <- function(obj, ..., chat, env = caller_env()) {
 contents_replay_class <- new_generic(
   "contents_replay_class",
   "cls",
-  function(cls, obj, ..., chat, env = rlang::caller_env()) {
+  function(cls, obj, ..., chat, env = caller_env()) {
     S7::S7_dispatch()
   }
 )
@@ -170,7 +170,7 @@ method(contents_replay_class, S7::S7_object) <- function(
   obj,
   ...,
   chat,
-  env = rlang::caller_env()
+  env = caller_env()
 ) {
   stopifnot(obj$version == 1)
 
@@ -183,19 +183,19 @@ method(contents_replay_class, S7::S7_object) <- function(
     pkg_cls <- strsplit(class_value, "::")[[1]]
     pkg_name <- pkg_cls[1]
 
-    rlang::check_installed(
+    check_installed(
       pkg_name,
       reason = "for `contents_replay()` to restore the chat content."
     )
     cls_name <- pkg_cls[2]
-    env <- rlang::ns_env(pkg_name)
+    env <- ns_env(pkg_name)
   } else {
     cls_name <- class_value
   }
 
   # While this seems like a bit of extra work, the tracebacks are accurate
   # vs referencing an unrelated parameter name in the traceback
-  rlang::exec(cls_name, !!!obj_props, .env = env)
+  exec(cls_name, !!!obj_props, .env = env)
 }
 
 
@@ -204,7 +204,7 @@ method(contents_replay_class, ToolDef) <- function(
   obj,
   ...,
   chat,
-  env = rlang::caller_env()
+  env = caller_env()
 ) {
   if (obj$version != 1) {
     cli::cli_abort(
@@ -244,23 +244,23 @@ method(contents_replay_class, ToolDef) <- function(
 #' @param env The environment to find non-package class constructors.
 #' @return The constructor function for the class.
 #' @noRd
-get_cls_constructor <- function(class_value, ..., env = rlang::caller_env()) {
-  rlang::check_dots_empty()
+get_cls_constructor <- function(class_value, ..., env = caller_env()) {
+  check_dots_empty()
 
   pkg_cls <- strsplit(class_value, "::")[[1]]
   if (length(pkg_cls) == 1) {
     # If the class is not a package class, return the object as is
     # This is the case for local S7 objects
-    rlang::eval_bare(rlang::sym(pkg_cls), env = env)
+    eval_bare(sym(pkg_cls), env = env)
   } else if (length(pkg_cls) == 2) {
     pkg_name <- pkg_cls[1]
     cls_name <- pkg_cls[2]
 
-    rlang::check_installed(
+    check_installed(
       pkg_name,
       reason = "for `contents_replay()` to restore the chat content."
     )
-    rlang::ns_env(pkg_name)[[cls_name]]
+    ns_env(pkg_name)[[cls_name]]
   } else {
     cli::cli_abort(
       "Invalid class name {.val {class_value[1]}}. Expected a single (or missing) `::` separator, not multiple.",
diff --git a/R/tools-def.R b/R/tools-def.R
index 5192eff1..5e746ff7 100644
--- a/R/tools-def.R
+++ b/R/tools-def.R
@@ -264,7 +264,7 @@ tool_reject <- function(
 ) {
   check_string(reason)
 
-  rlang::abort(
+  abort(
     paste("Tool call rejected.", reason),
     class = "ellmer_tool_reject"
   )

From 81dbaa617f0c6a2fcaaaff57379c7d8945803a02 Mon Sep 17 00:00:00 2001
From: Barret Schloerke <barret@posit.co>
Date: Mon, 9 Jun 2025 14:18:27 -0400
Subject: [PATCH 30/34] Remove unnecessary arg to `cli_abort()`. Add snapshot
 of error.

---
 R/content-replay.R                      | 20 ++++++--------------
 tests/testthat/_snaps/content-replay.md | 16 ++++++++++++++++
 tests/testthat/test-content-replay.R    |  4 ++++
 3 files changed, 26 insertions(+), 14 deletions(-)
 create mode 100644 tests/testthat/_snaps/content-replay.md

diff --git a/R/content-replay.R b/R/content-replay.R
index b0f3788a..909d4ded 100644
--- a/R/content-replay.R
+++ b/R/content-replay.R
@@ -52,8 +52,7 @@ contents_record <-
 
       if (!is_recorded_object(recorded)) {
         cli::cli_abort(
-          "Expected the recorded object to be a list with at least names 'version', 'class', and 'props'.",
-          call = caller_env()
+          "Expected the recorded object to be a list with at least names 'version', 'class', and 'props'."
         )
       }
 
@@ -62,8 +61,7 @@ contents_record <-
           length(recorded$class) != 1
       ) {
         cli::cli_abort(
-          "Expected the recorded object to have a single $class name, containing `::` if the class is from a package.",
-          call = caller_env()
+          "Expected the recorded object to have a single $class name, containing `::` if the class is from a package."
         )
       }
 
@@ -135,16 +133,12 @@ contents_replay <- function(obj, ..., chat, env = caller_env()) {
   cls <- get_cls_constructor(class_value[1], env = env)
 
   if (is.null(cls)) {
-    cli::cli_abort(
-      "Unable to find the S7 class: {.val {class_value[1]}}.",
-      call = caller_env()
-    )
+    cli::cli_abort("Unable to find the S7 class: {.val {class_value[1]}}.")
   }
 
   if (!S7_inherits(cls)) {
     cli::cli_abort(
-      "The object returned for {.val {class_value[1]}} is not an S7 class.",
-      call = caller_env()
+      "The object returned for {.val {class_value[1]}} is not an S7 class."
     )
   }
 
@@ -208,8 +202,7 @@ method(contents_replay_class, ToolDef) <- function(
 ) {
   if (obj$version != 1) {
     cli::cli_abort(
-      "Unsupported version {.val {obj$version}}.",
-      call = caller_env()
+      "Unsupported version {.val {obj$version}}."
     )
   }
 
@@ -263,8 +256,7 @@ get_cls_constructor <- function(class_value, ..., env = caller_env()) {
     ns_env(pkg_name)[[cls_name]]
   } else {
     cli::cli_abort(
-      "Invalid class name {.val {class_value[1]}}. Expected a single (or missing) `::` separator, not multiple.",
-      call = caller_env()
+      "Invalid class name {.val {class_value[1]}}. Expected a single (or missing) `::` separator, not multiple."
     )
   }
 }
diff --git a/tests/testthat/_snaps/content-replay.md b/tests/testthat/_snaps/content-replay.md
new file mode 100644
index 00000000..2d847891
--- /dev/null
+++ b/tests/testthat/_snaps/content-replay.md
@@ -0,0 +1,16 @@
+# unknown classes cause errors
+
+    Code
+      contents_replay(recorded, chat = chat)
+    Condition
+      Error in `contents_replay()`:
+      ! Unable to find the S7 class: "ellmer::Turn2".
+
+# replay classes are S7 classes
+
+    Code
+      contents_replay(recorded, chat = chat)
+    Condition
+      Error in `contents_replay()`:
+      ! The object returned for "LocalClass" is not an S7 class.
+
diff --git a/tests/testthat/test-content-replay.R b/tests/testthat/test-content-replay.R
index 61874a46..5d0f0308 100644
--- a/tests/testthat/test-content-replay.R
+++ b/tests/testthat/test-content-replay.R
@@ -216,6 +216,8 @@ test_that("unknown classes cause errors", {
     contents_replay(recorded, chat = chat),
     "Unable to find the S7 class"
   )
+
+  expect_snapshot(contents_replay(recorded, chat = chat), error = TRUE)
 })
 
 test_that("replay classes are S7 classes", {
@@ -238,4 +240,6 @@ test_that("replay classes are S7 classes", {
     contents_replay(recorded, chat = chat),
     "is not an S7 class"
   )
+
+  expect_snapshot(contents_replay(recorded, chat = chat), error = TRUE)
 })

From 9bbab27abf3bcea8f4c262343376bfbe03512df5 Mon Sep 17 00:00:00 2001
From: Barret Schloerke <barret@posit.co>
Date: Mon, 9 Jun 2025 14:30:23 -0400
Subject: [PATCH 31/34] Move `cls` assertions inside `get_cls_constructor()`

---
 R/content-replay.R                      | 25 ++++++++++++-------------
 tests/testthat/_snaps/content-replay.md |  4 ++--
 2 files changed, 14 insertions(+), 15 deletions(-)

diff --git a/R/content-replay.R b/R/content-replay.R
index 909d4ded..f1d89be4 100644
--- a/R/content-replay.R
+++ b/R/content-replay.R
@@ -131,17 +131,6 @@ contents_replay <- function(obj, ..., chat, env = caller_env()) {
   }
 
   cls <- get_cls_constructor(class_value[1], env = env)
-
-  if (is.null(cls)) {
-    cli::cli_abort("Unable to find the S7 class: {.val {class_value[1]}}.")
-  }
-
-  if (!S7_inherits(cls)) {
-    cli::cli_abort(
-      "The object returned for {.val {class_value[1]}} is not an S7 class."
-    )
-  }
-
   # Manually retrieve the handler for the class as we dispatch on the class itself,
   # not on an instance
   # An error will be thrown if a method is not found,
@@ -244,7 +233,7 @@ get_cls_constructor <- function(class_value, ..., env = caller_env()) {
   if (length(pkg_cls) == 1) {
     # If the class is not a package class, return the object as is
     # This is the case for local S7 objects
-    eval_bare(sym(pkg_cls), env = env)
+    cls <- eval_bare(sym(pkg_cls), env = env)
   } else if (length(pkg_cls) == 2) {
     pkg_name <- pkg_cls[1]
     cls_name <- pkg_cls[2]
@@ -253,12 +242,22 @@ get_cls_constructor <- function(class_value, ..., env = caller_env()) {
       pkg_name,
       reason = "for `contents_replay()` to restore the chat content."
     )
-    ns_env(pkg_name)[[cls_name]]
+    cls <- ns_env(pkg_name)[[cls_name]]
   } else {
     cli::cli_abort(
       "Invalid class name {.val {class_value[1]}}. Expected a single (or missing) `::` separator, not multiple."
     )
   }
+  if (is.null(cls)) {
+    cli::cli_abort("Unable to find the S7 class: {.val {class_value[1]}}.")
+  }
+
+  if (!S7_inherits(cls)) {
+    cli::cli_abort(
+      "The object returned for {.val {class_value[1]}} is not an S7 class."
+    )
+  }
+  cls
 }
 
 prop_is_read_only <- function(prop) {
diff --git a/tests/testthat/_snaps/content-replay.md b/tests/testthat/_snaps/content-replay.md
index 2d847891..d2dc4f0a 100644
--- a/tests/testthat/_snaps/content-replay.md
+++ b/tests/testthat/_snaps/content-replay.md
@@ -3,7 +3,7 @@
     Code
       contents_replay(recorded, chat = chat)
     Condition
-      Error in `contents_replay()`:
+      Error in `get_cls_constructor()`:
       ! Unable to find the S7 class: "ellmer::Turn2".
 
 # replay classes are S7 classes
@@ -11,6 +11,6 @@
     Code
       contents_replay(recorded, chat = chat)
     Condition
-      Error in `contents_replay()`:
+      Error in `get_cls_constructor()`:
       ! The object returned for "LocalClass" is not an S7 class.
 

From 9f52544eb67a8c28dab74dbf5839b5d3c5f45afe Mon Sep 17 00:00:00 2001
From: Barret Schloerke <barret@posit.co>
Date: Mon, 9 Jun 2025 14:45:11 -0400
Subject: [PATCH 32/34] Remove non-exported param docs

---
 R/content-replay.R     | 1 -
 man/contents_record.Rd | 2 --
 2 files changed, 3 deletions(-)

diff --git a/R/content-replay.R b/R/content-replay.R
index f1d89be4..7525f5b4 100644
--- a/R/content-replay.R
+++ b/R/content-replay.R
@@ -17,7 +17,6 @@ NULL
 #'
 #' @param content A [Turn] or [Content] object to serialize.
 #' @param obj A basic list to desierialize.
-#' @param cls The class constructor to be used for replaying the object.
 #' @param chat A [Chat] object to be used for context.
 #' @param env The environment to find non-package classes.
 #' @param ... Not used.
diff --git a/man/contents_record.Rd b/man/contents_record.Rd
index f38a615e..b7f2a925 100644
--- a/man/contents_record.Rd
+++ b/man/contents_record.Rd
@@ -19,8 +19,6 @@ contents_replay(obj, ..., chat, env = caller_env())
 \item{obj}{A basic list to desierialize.}
 
 \item{env}{The environment to find non-package classes.}
-
-\item{cls}{The class constructor to be used for replaying the object.}
 }
 \description{
 These generic functions can be use to convert \link{Turn}/\link{Content} objects

From 3465cb444c7a424894d8a16b6f3b2b3086dc6064 Mon Sep 17 00:00:00 2001
From: Barret Schloerke <barret@posit.co>
Date: Mon, 9 Jun 2025 16:05:31 -0400
Subject: [PATCH 33/34] Only support (and enforce) ellmer s7 objects.

---
 R/content-replay.R     | 153 +++++++++++++++--------------------------
 man/contents_record.Rd |   4 +-
 2 files changed, 55 insertions(+), 102 deletions(-)

diff --git a/R/content-replay.R b/R/content-replay.R
index 7525f5b4..881a2859 100644
--- a/R/content-replay.R
+++ b/R/content-replay.R
@@ -2,7 +2,6 @@
 #' @include turns.R
 #' @include tools-def.R
 #' @include content.R
-
 NULL
 
 #' Save and restore content
@@ -18,7 +17,6 @@ NULL
 #' @param content A [Turn] or [Content] object to serialize.
 #' @param obj A basic list to desierialize.
 #' @param chat A [Chat] object to be used for context.
-#' @param env The environment to find non-package classes.
 #' @param ... Not used.
 #'
 #' @examplesIf has_credentials("openai")
@@ -41,12 +39,6 @@ contents_record <-
     function(content, ..., chat) {
       check_chat(chat, call = caller_env())
 
-      if (is_list_of_s7_objects(content)) {
-        # If the content is a list, we need to record each element
-        # and return a list of the recorded elements
-        return(lapply(content, contents_record, chat = chat))
-      }
-
       recorded <- S7::S7_dispatch()
 
       if (!is_recorded_object(recorded)) {
@@ -64,6 +56,12 @@ contents_record <-
         )
       }
 
+      if (!grepl("ellmer::", recorded$class, fixed = TRUE)) {
+        cli::cli_abort(
+          "Only S7 classes from the `ellmer` package are currently supported. Received: {.val {recorded$class}}."
+        )
+      }
+
       recorded
     }
   )
@@ -79,11 +77,10 @@ method(contents_record, S7::S7_object) <- function(content, ..., chat) {
     lapply(prop_names, function(prop_name) {
       prop_value <- S7::prop(prop_name, object = content)
       if (S7_inherits(prop_value)) {
-        # Recursive call to S7 object
+        # Recursive record for S7 objects
         contents_record(prop_value, chat = chat)
       } else if (is_list_of_s7_objects(prop_value)) {
-        # Make record of each item in prop.
-        # Do not recurse forever!
+        # Make record of each item in list
         lapply(prop_value, contents_record, chat = chat)
       } else {
         prop_value
@@ -106,42 +103,57 @@ method(contents_record, S7::S7_object) <- function(content, ..., chat) {
 #' @rdname contents_record
 #' @export
 # Holy "Holy Trait" dispatching, Batman!
-contents_replay <- function(obj, ..., chat, env = caller_env()) {
+contents_replay <- function(obj, ..., chat) {
   check_chat(chat, call = caller_env())
 
   # Find any reason to not believe `obj` is a recorded object.
   # If not a recorded object, return it as is.
   # If it is a recorded s7 object, dispatch on the discovered class.
 
-  if (!is.list(obj)) {
-    return(obj)
+  if (!is_recorded_object(obj)) {
+    cli::cli_abort(
+      "Expected the object to be a list with at least names 'version', 'class', and 'props'."
+    )
   }
 
-  if (!is_recorded_object(obj)) {
-    if (is_list_of_recorded_objects(obj)) {
-      return(lapply(obj, contents_replay, chat = chat, env = env))
-    }
-    return(obj)
+  class_name <- obj$class
+  if (!(is.character(class_name) && length(class_name) == 1)) {
+    cli::cli_abort(
+      "Expected the replay object's `'class'` value to be a single character."
+    )
+  }
+
+  cls_name <- strsplit(class_name, "::")[[1]][2]
+  if (!grepl("ellmer::", class_name, fixed = TRUE)) {
+    cli::cli_abort(
+      "Only S7 classes from the `ellmer` package are currently supported."
+    )
+  }
+
+  cls <- pkg_env("ellmer")[[cls_name]]
+
+  if (is.null(cls)) {
+    cli::cli_abort("Unable to find the S7 class: {.val {class_name}}.")
   }
 
-  class_value <- obj$class
-  if (!(is.character(class_value) && length(class_value) > 0)) {
-    return(obj)
+  if (!S7_inherits(cls)) {
+    cli::cli_abort(
+      "The object returned for {.val {class_name}} is not an S7 class."
+    )
   }
 
-  cls <- get_cls_constructor(class_value[1], env = env)
   # Manually retrieve the handler for the class as we dispatch on the class itself,
   # not on an instance
   # An error will be thrown if a method is not found,
   # however we have a fallback for the `S7::S7_object` (the root base class)
   handler <- S7::method(contents_replay_class, cls)
-  handler(cls, obj, chat = chat, env = env)
+  handler(cls, obj, chat = chat)
 }
 
 contents_replay_class <- new_generic(
   "contents_replay_class",
   "cls",
-  function(cls, obj, ..., chat, env = caller_env()) {
+  function(cls, obj, ..., chat) {
     S7::S7_dispatch()
   }
 )
@@ -151,42 +163,34 @@ method(contents_replay_class, S7::S7_object) <- function(
   cls,
   obj,
   ...,
-  chat,
-  env = caller_env()
+  chat
 ) {
   stopifnot(obj$version == 1)
 
-  obj_props <- lapply(obj$props, contents_replay, chat = chat)
-
-  class_value <- obj$class[1]
-  if (grepl("::", class_value, fixed = TRUE)) {
-    # If the class is a package class, use the package name to find the constructor
-    # This allows use to reach into private namespaces within the package
-    pkg_cls <- strsplit(class_value, "::")[[1]]
-    pkg_name <- pkg_cls[1]
-
-    check_installed(
-      pkg_name,
-      reason = "for `contents_replay()` to restore the chat content."
-    )
-    cls_name <- pkg_cls[2]
-    env <- ns_env(pkg_name)
-  } else {
-    cls_name <- class_value
-  }
+  obj_props <- map(obj$props, function(prop_value) {
+    if (is_list_of_recorded_objects(prop_value)) {
+      # If the prop is a list of recorded objects, replay each one
+      map(prop_value, contents_replay, chat = chat)
+    } else if (is_recorded_object(prop_value)) {
+      # If the prop is a recorded object, replay it
+      contents_replay(prop_value, chat = chat)
+    } else {
+      prop_value
+    }
+  })
 
+  class_name <- obj$class[1]
+  cls_name <- strsplit(class_name, "::")[[1]][2]
   # While this seems like a bit of extra work, the tracebacks are accurate
   # vs referencing an unrelated parameter name in the traceback
-  exec(cls_name, !!!obj_props, .env = env)
+  exec(cls_name, !!!obj_props, .env = ns_env("ellmer"))
 }
 
-
 method(contents_replay_class, ToolDef) <- function(
   cls,
   obj,
   ...,
-  chat,
-  env = caller_env()
+  chat
 ) {
   if (obj$version != 1) {
     cli::cli_abort(
@@ -205,60 +209,11 @@ method(contents_replay_class, ToolDef) <- function(
   ret <- contents_replay_class(
     super(cls, S7::S7_object),
     obj,
-    chat = chat,
-    env = env
+    chat = chat
   )
   ret
 }
 
-
-#' Retrieve the class constructor
-#'
-#' @description
-#' The class for S7 Classes are stored as "package::class" in the recorded object.
-#' However, it does not mean that the class constructor is exported in the namespace.
-#' Therefore, this function will reach into the package environment to retrieve the constructor.
-#' If the class is not a _package_ class, it will return the object as is given the `env`.
-#'
-#' @param class_value The single string representing the `package::class` to retrieve the constructor.
-#' @param ... Not used.
-#' @param env The environment to find non-package class constructors.
-#' @return The constructor function for the class.
-#' @noRd
-get_cls_constructor <- function(class_value, ..., env = caller_env()) {
-  check_dots_empty()
-
-  pkg_cls <- strsplit(class_value, "::")[[1]]
-  if (length(pkg_cls) == 1) {
-    # If the class is not a package class, return the object as is
-    # This is the case for local S7 objects
-    cls <- eval_bare(sym(pkg_cls), env = env)
-  } else if (length(pkg_cls) == 2) {
-    pkg_name <- pkg_cls[1]
-    cls_name <- pkg_cls[2]
-
-    check_installed(
-      pkg_name,
-      reason = "for `contents_replay()` to restore the chat content."
-    )
-    cls <- ns_env(pkg_name)[[cls_name]]
-  } else {
-    cli::cli_abort(
-      "Invalid class name {.val {class_value[1]}}. Expected a single (or missing) `::` separator, not multiple."
-    )
-  }
-  if (is.null(cls)) {
-    cli::cli_abort("Unable to find the S7 class: {.val {class_value[1]}}.")
-  }
-
-  if (!S7_inherits(cls)) {
-    cli::cli_abort(
-      "The object returned for {.val {class_value[1]}} is not an S7 class."
-    )
-  }
-  cls
-}
-
 prop_is_read_only <- function(prop) {
   is.function(prop$getter) && !is.function(prop$setter)
 }
diff --git a/man/contents_record.Rd b/man/contents_record.Rd
index b7f2a925..f8c9d3d5 100644
--- a/man/contents_record.Rd
+++ b/man/contents_record.Rd
@@ -7,7 +7,7 @@
 \usage{
 contents_record(content, ..., chat)
 
-contents_replay(obj, ..., chat, env = caller_env())
+contents_replay(obj, ..., chat)
 }
 \arguments{
 \item{content}{A \link{Turn} or \link{Content} object to serialize.}
@@ -17,8 +17,6 @@ contents_replay(obj, ..., chat, env = caller_env())
 \item{chat}{A \link{Chat} object to be used for context.}
 
 \item{obj}{A basic list to desierialize.}
-
-\item{env}{The environment to find non-package classes.}
 }
 \description{
 These generic functions can be use to convert \link{Turn}/\link{Content} objects

From eefd37f4f4b422d012d8c5b3f71028aa8b383b92 Mon Sep 17 00:00:00 2001
From: Barret Schloerke <barret@posit.co>
Date: Mon, 9 Jun 2025 16:07:24 -0400
Subject: [PATCH 34/34] Update test for (now unsupported) local s7 class

Also remove now _difficult to test_ "returns non-s7 object" from `contents_replay()`
---
 tests/testthat/_snaps/content-replay.md | 23 ++++++++++++++++-------
 tests/testthat/test-content-replay.R    | 19 ++++++++++++++++---
 2 files changed, 32 insertions(+), 10 deletions(-)

diff --git a/tests/testthat/_snaps/content-replay.md b/tests/testthat/_snaps/content-replay.md
index d2dc4f0a..4846271c 100644
--- a/tests/testthat/_snaps/content-replay.md
+++ b/tests/testthat/_snaps/content-replay.md
@@ -1,16 +1,25 @@
-# unknown classes cause errors
+# non-ellmer classes are recorded/replayed by default
 
     Code
-      contents_replay(recorded, chat = chat)
+      contents_record(LocalClass("testname"), chat = chat)
     Condition
-      Error in `get_cls_constructor()`:
-      ! Unable to find the S7 class: "ellmer::Turn2".
+      Error in `contents_record()`:
+      ! Only S7 classes from the `ellmer` package are currently supported. Received: "LocalClass".
 
-# replay classes are S7 classes
+---
+
+    Code
+      contents_replay(list(version = 1, class = "testpkg::LocalClass", props = list(
+        name = "testname")), chat = chat)
+    Condition
+      Error in `contents_replay()`:
+      ! Only S7 classes from the `ellmer` package are currently supported.
+
+# unknown classes cause errors
 
     Code
       contents_replay(recorded, chat = chat)
     Condition
-      Error in `get_cls_constructor()`:
-      ! The object returned for "LocalClass" is not an S7 class.
+      Error in `contents_replay()`:
+      ! Unable to find the S7 class: "ellmer::Turn2".
 
diff --git a/tests/testthat/test-content-replay.R b/tests/testthat/test-content-replay.R
index 5d0f0308..b72a872e 100644
--- a/tests/testthat/test-content-replay.R
+++ b/tests/testthat/test-content-replay.R
@@ -190,7 +190,7 @@ test_that("can round trip of ContentPDF record/replay", {
   test_record_replay(ContentPDF(type = "TYPE", data = "DATA"))
 })
 
-test_that("non-package classes are recorded/replayed by default", {
+test_that("non-ellmer classes are not recorded/replayed by default", {
   chat <- chat_openai_test()
 
   LocalClass <- S7::new_class(
@@ -203,10 +203,23 @@ test_that("non-package classes are recorded/replayed by default", {
     package = NULL
   )
 
-  test_record_replay(LocalClass("testname"), chat = chat)
+  expect_snapshot(
+    contents_record(LocalClass("testname"), chat = chat),
+    error = TRUE
+  )
+  expect_snapshot(
+    contents_replay(
+      list(
+        version = 1,
+        class = "testpkg::LocalClass",
+        props = list(name = "testname")
+      ),
+      chat = chat
+    ),
+    error = TRUE
+  )
 })
 
-
 test_that("unknown classes cause errors", {
   chat <- chat_openai_test()
   recorded <- contents_record(Turn("user"), chat = chat)