diff --git a/Sources/AsyncHTTPClient/HTTPClient.swift b/Sources/AsyncHTTPClient/HTTPClient.swift
index e523a8f7d..02e450476 100644
--- a/Sources/AsyncHTTPClient/HTTPClient.swift
+++ b/Sources/AsyncHTTPClient/HTTPClient.swift
@@ -795,7 +795,8 @@ public class HTTPClient {
 
             self.poolManager.executeRequest(requestBag)
         } catch {
-            task.fail(with: error, delegateType: Delegate.self)
+            delegate.didReceiveError(task: task, error)
+            task.failInternal(with: error)
         }
 
         return task
diff --git a/Sources/AsyncHTTPClient/HTTPHandler.swift b/Sources/AsyncHTTPClient/HTTPHandler.swift
index fdca88982..8d92d8ef7 100644
--- a/Sources/AsyncHTTPClient/HTTPHandler.swift
+++ b/Sources/AsyncHTTPClient/HTTPHandler.swift
@@ -1024,9 +1024,9 @@ extension HTTPClient {
             taskDelegate?.fail(error)
         }
 
-        func fail<Delegate: HTTPClientResponseDelegate>(
-            with error: Error,
-            delegateType: Delegate.Type
+        /// Called internally only, used to fail a task from within the state machine functionality.
+        func failInternal(
+            with error: Error
         ) {
             self.promise.fail(error)
         }
diff --git a/Sources/AsyncHTTPClient/RequestBag.swift b/Sources/AsyncHTTPClient/RequestBag.swift
index d40e6ca04..f206325ee 100644
--- a/Sources/AsyncHTTPClient/RequestBag.swift
+++ b/Sources/AsyncHTTPClient/RequestBag.swift
@@ -120,7 +120,7 @@ final class RequestBag<Delegate: HTTPClientResponseDelegate & Sendable>: Sendabl
             executor.cancelRequest(self)
         case .failTaskAndCancelExecutor(let error, let executor):
             self.delegate.didReceiveError(task: self.task, error)
-            self.task.fail(with: error, delegateType: Delegate.self)
+            self.task.failInternal(with: error)
             executor.cancelRequest(self)
         case .none:
             break
@@ -181,7 +181,7 @@ final class RequestBag<Delegate: HTTPClientResponseDelegate & Sendable>: Sendabl
         switch action {
         case .failTask(let error):
             self.delegate.didReceiveError(task: self.task, error)
-            self.task.fail(with: error, delegateType: Delegate.self)
+            self.task.failInternal(with: error)
             return self.task.eventLoop.makeFailedFuture(error)
 
         case .failFuture(let error):
diff --git a/Tests/AsyncHTTPClientTests/HTTPClientTests.swift b/Tests/AsyncHTTPClientTests/HTTPClientTests.swift
index b47cbe444..307e56fd3 100644
--- a/Tests/AsyncHTTPClientTests/HTTPClientTests.swift
+++ b/Tests/AsyncHTTPClientTests/HTTPClientTests.swift
@@ -3357,6 +3357,40 @@ final class HTTPClientTests: XCTestCaseHTTPClientTestsBaseClass {
         XCTAssertNoThrow(try future.wait())
     }
 
+    func testDelegateGetsErrorsFromCreatingRequestBag() throws {
+        // We want to test that we propagate errors to the delegate from failures to construct the
+        // request bag. Those errors only come from invalid headers.
+        final class TestDelegate: HTTPClientResponseDelegate, Sendable {
+            typealias Response = Void
+            let error: NIOLockedValueBox<Error?> = .init(nil)
+            func didFinishRequest(task: HTTPClient.Task<Void>) throws {}
+            func didReceiveError(task: HTTPClient.Task<Response>, _ error: Error) {
+                self.error.withLockedValue { $0 = error }
+            }
+        }
+
+        let httpClient = HTTPClient(
+            eventLoopGroupProvider: .shared(self.clientGroup)
+        )
+
+        defer {
+            XCTAssertNoThrow(try httpClient.syncShutdown())
+        }
+
+        // 198.51.100.254 is reserved for documentation only
+        var request = try HTTPClient.Request(url: "http://198.51.100.254:65535/get")
+        request.headers.replaceOrAdd(name: "Not-ASCII", value: "not-fine\n")
+        let delegate = TestDelegate()
+
+        XCTAssertThrowsError(try httpClient.execute(request: request, delegate: delegate).wait()) {
+            XCTAssertEqualTypeAndValue($0, HTTPClientError.invalidHeaderFieldValues(["not-fine\n"]))
+            XCTAssertEqualTypeAndValue(
+                delegate.error.withLockedValue { $0 },
+                HTTPClientError.invalidHeaderFieldValues(["not-fine\n"])
+            )
+        }
+    }
+
     func testContentLengthTooLongFails() throws {
         let url = self.defaultHTTPBinURLPrefix + "post"
         XCTAssertThrowsError(