diff --git a/.flake8 b/.flake8
new file mode 100644
index 000000000..ed8440b87
--- /dev/null
+++ b/.flake8
@@ -0,0 +1,16 @@
+[flake8]
+ignore = W503, C901, ANN101
+max-line-length = 88
+exclude = cookiecutter
+per-file-ignores =
+    # Don't require docstrings or type annotations in tests
+    # tests/*:D100,D102,D103,DAR,ANN
+    # Don't require docstrings conventions or type annotations in SDK samples
+    # samples/*:ANN,DAR
+    # Don't require docstrings conventions or type annotations in private modules
+    singer_sdk/helpers/_*.py:ANN,DAR,D105
+    # Don't require docstrings conventions in "meta" code
+    # singer_sdk/helpers/_classproperty.py:D105
+max-complexity = 10
+docstring-convention = google
+allow-star-arg-any = true
diff --git a/.github/workflows/constraints.txt b/.github/workflows/constraints.txt
index 16d1c013e..407d9fafc 100644
--- a/.github/workflows/constraints.txt
+++ b/.github/workflows/constraints.txt
@@ -2,3 +2,5 @@ pip==22.1.2
 poetry==1.1.13
 virtualenv==20.15.1
 changelog-cli==0.7.1
+nox==2022.1.7
+nox-poetry==1.0.1
diff --git a/.github/workflows/test.yml b/.github/workflows/test.yml
index b2ab35cb9..cbf78a875 100644
--- a/.github/workflows/test.yml
+++ b/.github/workflows/test.yml
@@ -8,20 +8,25 @@ on:
   workflow_dispatch:
     inputs: {}
 
+env:
+  FORCE_COLOR: "1"
+
 jobs:
   tests:
-    name: Test on ${{ matrix.python-version }} (${{ matrix.tox-env }}) / ${{ matrix.os }}
+    name: Test on ${{ matrix.python-version }} (${{ matrix.session }}) / ${{ matrix.os }}
     runs-on: ${{ matrix.os }}
+    env:
+      NOXSESSION: ${{ matrix.session }}
     strategy:
       fail-fast: false
       matrix:
         include:
-        - { tox-env: py, python-version: "3.7", os: "ubuntu-latest" }
-        - { tox-env: py, python-version: "3.8", os: "ubuntu-latest" }
-        - { tox-env: py, python-version: "3.9", os: "ubuntu-latest" }
-        - { tox-env: py, python-version: "3.10", os: "ubuntu-latest" }
-        - { tox-env: doctest, python-version: "3.10", os: "ubuntu-latest" }
-        - { tox-env: mypy, python-version: "3.8", os: "ubuntu-latest" }
+        - { session: tests,   python-version: "3.7",  os: "ubuntu-latest" }
+        - { session: tests,   python-version: "3.8",  os: "ubuntu-latest" }
+        - { session: tests,   python-version: "3.9",  os: "ubuntu-latest" }
+        - { session: tests,   python-version: "3.10", os: "ubuntu-latest" }
+        - { session: doctest, python-version: "3.10", os: "ubuntu-latest" }
+        - { session: mypy,    python-version: "3.8",  os: "ubuntu-latest" }
 
     steps:
     - name: Check out the repository
@@ -39,7 +44,8 @@ jobs:
       with:
         python-version: ${{ matrix.python-version }}
         architecture: x64
-        cache: 'poetry'
+        cache: 'pip'
+        cache-dependency-path: 'poetry.lock'
 
     - name: Upgrade pip
       env:
@@ -48,17 +54,20 @@ jobs:
         pip install pip
         pip --version
 
-    - name: Install Dependencies
+    - name: Install Nox
+      env:
+        PIP_CONSTRAINT: .github/workflows/constraints.txt
       run: |
-        poetry env use "${{ matrix.python-version }}"
-        poetry install
+        pipx install --pip-args=--constraint=.github/workflows/constraints.txt nox
+        pipx inject --pip-args=--constraint=.github/workflows/constraints.txt nox nox-poetry
+        nox --version
 
-    - name: Run tox
+    - name: Run Nox
       run: |
-        poetry run tox -e ${{ matrix.tox-env }} --${{ matrix.doctest && ' --doctest-modules singer_sdk' }}
+        nox --python=${{ matrix.python-version }}
 
     - name: Upload coverage data
-      if: always() && (matrix.tox-env == 'py')
+      if: always() && (matrix.session == 'tests')
       uses: actions/upload-artifact@v3.1.0
       with:
         name: coverage-data
@@ -93,7 +102,8 @@ jobs:
       with:
         python-version: '3.10'
         architecture: x64
-        cache: 'poetry'
+        cache: 'pip'
+        cache-dependency-path: 'poetry.lock'
 
     - name: Upgrade pip
       env:
@@ -102,14 +112,17 @@ jobs:
         pip install pip
         pip --version
 
-    - name: Install Dependencies
+    - name: Install Nox
+      env:
+        PIP_CONSTRAINT: .github/workflows/constraints.txt
       run: |
-        poetry env use "3.10"
-        poetry install
+        pipx install --pip-args=--constraint=.github/workflows/constraints.txt nox
+        pipx inject --pip-args=--constraint=.github/workflows/constraints.txt nox nox-poetry
+        nox --version
 
-    - name: Run tox
+    - name: Run Nox
       run: |
-        poetry run tox -e py -- -m "external"
+        nox -s tests -p 3.10 -- -m "external"
 
   coverage:
     name: Coverage
@@ -128,7 +141,8 @@ jobs:
       uses: actions/setup-python@v4.0.0
       with:
         python-version: '3.10'
-        cache: 'poetry'
+        cache: 'pip'
+        cache-dependency-path: 'poetry.lock'
 
     - name: Upgrade pip
       run: |
@@ -140,18 +154,21 @@ jobs:
       with:
         name: coverage-data
 
-    - name: Install Dependencies
+    - name: Install Nox
+      env:
+        PIP_CONSTRAINT: .github/workflows/constraints.txt
       run: |
-        poetry env use "3.10"
-        poetry install
+        pipx install --pip-args=--constraint=.github/workflows/constraints.txt nox
+        pipx inject --pip-args=--constraint=.github/workflows/constraints.txt nox nox-poetry
+        nox --version
 
     - name: Combine coverage data and display human readable report
       run: |
-        poetry run tox -e combine_coverage
+        nox --session=coverage
 
     - name: Create coverage report
       run: |
-        poetry run tox -e coverage_artifact -- xml
+        nox --session=coverage -- xml
 
     - name: Upload coverage report
       uses: codecov/codecov-action@v3.1.0
diff --git a/docs/CONTRIBUTING.md b/docs/CONTRIBUTING.md
index b0bc5589e..b310e3005 100644
--- a/docs/CONTRIBUTING.md
+++ b/docs/CONTRIBUTING.md
@@ -15,7 +15,7 @@ Contributors are expected to follow our [Code of Conduct](https://docs.meltano.c
 ## Setting up Prereqs
 
 Make sure [`poetry`](https://python-poetry.org/docs/),
-[`pre-commit`](https://pre-commit.com/) and [`tox`](https://tox.wiki/en/latest/)
+[`pre-commit`](https://pre-commit.com/) and [`nox`](https://nox.thea.codes/en/stable/)
 are installed. You can use [`pipx`](https://pypa.github.io/pipx/) to install
 all of them. To install `pipx`:
 
@@ -29,7 +29,8 @@ With `pipx` installed, you globally add the required tools:
 ```bash
 pipx install poetry
 pipx install pre-commit
-pipx install tox
+pipx install nox
+pipx install nox-poetry
 ```
 
 Now you can use Poetry to install package dependencies:
@@ -55,18 +56,18 @@ First clone, then...
     - `poetry install -E docs`
 1. The project has `pre-commit` hooks. Install them with:
     - `pre-commit install`
-1. Most development tasks you might need should be covered by `tox` environments. You can use `tox -l` to list all available tasks.
+1. Most development tasks you might need should be covered by `nox` sessions. You can use `nox -l` to list all available tasks.
 For example:
 
-    - Run unit tests: `tox -e py`.
+    - Run unit tests: `nox -r`.
 
       We use `coverage` for code coverage metrics.
 
-    - Run pre-commit hooks: `tox -e pre-commit`.
+    - Run pre-commit hooks: `pre-commit run --all`.
 
       We use `black`, `flake8`, `isort`, `mypy` and `pyupgrade`. The project-wide max line length is `88`.
 
-    - Build documentation: `tox -e docs`
+    - Build documentation: `nox -rs docs`
 
       We use `sphinx` to build documentation.
 
@@ -84,22 +85,16 @@ To run tests:
 
 ```bash
 # Run just the core and cookiecutter tests (no external creds required):
-tox -e py
+nox -rs tests
 
 # Run all tests (external creds required):
-tox -e py -- -m "external"
-```
-
-To gather and display coverage metrics:
-
-```bash
-tox -e combine_coverage
+nox -rs tests -- -m "external"
 ```
 
 To view the code coverage report in HTML format:
 
 ```bash
-tox -e coverage_artifact -- html && open ./htmlcov/index.html
+nox -rs coverage -- html && open ./htmlcov/index.html
 ```
 
 ## Testing Updates to Docs
@@ -113,7 +108,7 @@ To build the docs:
 
 ```bash
 # Build docs
-tox -e docs
+nox -rs docs
 
 # Open in the local browser:
 open build/index.html
diff --git a/noxfile.py b/noxfile.py
new file mode 100644
index 000000000..07f6e2b52
--- /dev/null
+++ b/noxfile.py
@@ -0,0 +1,128 @@
+"""Nox configuration."""
+
+from __future__ import annotations
+
+import os
+import shutil
+import sys
+from pathlib import Path
+from textwrap import dedent
+
+import nox
+
+try:
+    from nox_poetry import Session, session
+except ImportError:
+    message = f"""\
+    Nox failed to import the 'nox-poetry' package.
+    Please install it using the following command:
+    {sys.executable} -m pip install nox-poetry"""
+    raise SystemExit(dedent(message)) from None
+
+package = "singer_sdk"
+python_versions = ["3.10", "3.9", "3.8", "3.7"]
+main_python_version = "3.10"
+locations = "singer_sdk", "tests", "noxfile.py", "docs/conf.py"
+nox.options.sessions = (
+    "mypy",
+    "tests",
+    "doctest",
+)
+
+
+@session(python=python_versions)
+def mypy(session: Session) -> None:
+    """Check types with mypy."""
+    args = session.posargs or ["singer_sdk"]
+    session.install(".")
+    session.install(
+        "mypy",
+        "sqlalchemy2-stubs",
+        "types-python-dateutil",
+        "types-requests",
+    )
+    session.run("mypy", *args)
+    if not session.posargs:
+        session.run("mypy", f"--python-executable={sys.executable}", "noxfile.py")
+
+
+@session(python=python_versions)
+def tests(session: Session) -> None:
+    """Execute pytest tests and compute coverage."""
+    session.install(".")
+    session.install(
+        "coverage[toml]",
+        "pytest",
+        "freezegun",
+        "pandas",
+        "pyarrow",
+        "requests-mock",
+        # Cookiecutter tests
+        "black",
+        "cookiecutter",
+        "PyYAML",
+        "darglint",
+        "flake8",
+        "flake8-annotations",
+        "flake8-docstrings",
+        "mypy",
+    )
+
+    try:
+        session.run(
+            "coverage",
+            "run",
+            "--parallel",
+            "-m",
+            "pytest",
+            "-x",
+            "-v",
+            *session.posargs,
+        )
+    finally:
+        if session.interactive:
+            session.notify("coverage", posargs=[])
+
+
+@session(python=python_versions)
+def doctest(session: Session) -> None:
+    """Run examples with xdoctest."""
+    if session.posargs:
+        args = [package, *session.posargs]
+    else:
+        args = [package]
+        if "FORCE_COLOR" in os.environ:
+            args.append("--xdoctest-colored=1")
+
+    session.install(".")
+    session.install("pytest", "xdoctest[colors]")
+    session.run("pytest", "--xdoctest", *args)
+
+
+@session(python=main_python_version)
+def coverage(session: Session) -> None:
+    """Generate coverage report."""
+    args = session.posargs or ["report"]
+
+    session.install("coverage[toml]")
+
+    if not session.posargs and any(Path().glob(".coverage.*")):
+        session.run("coverage", "combine")
+
+    session.run("coverage", *args)
+
+
+@session(name="docs", python=main_python_version)
+def docs(session: Session) -> None:
+    """Build the documentation."""
+    args = session.posargs or ["docs", "build", "-W"]
+    if not session.posargs and "FORCE_COLOR" in os.environ:
+        args.insert(0, "--color")
+
+    session.install(".[docs]")
+
+    build_dir = Path("build")
+    if build_dir.exists():
+        shutil.rmtree(build_dir)
+
+    session.run("sphinx-build", *args)
diff --git a/poetry.lock b/poetry.lock
index 056da3790..8a6a42ccd 100644
--- a/poetry.lock
+++ b/poetry.lock
@@ -225,14 +225,6 @@ category = "main"
 optional = false
 python-versions = ">=3.5"
 
-[[package]]
-name = "distlib"
-version = "0.3.4"
-description = "Distribution utilities"
-category = "dev"
-optional = false
-python-versions = "*"
-
 [[package]]
 name = "docutils"
 version = "0.16"
@@ -241,18 +233,6 @@ category = "main"
 optional = true
 python-versions = ">=2.7, !=3.0.*, !=3.1.*, !=3.2.*, !=3.3.*, !=3.4.*"
 
-[[package]]
-name = "filelock"
-version = "3.4.1"
-description = "A platform independent file lock."
-category = "dev"
-optional = false
-python-versions = ">=3.6"
-
-[package.extras]
-docs = ["furo (>=2021.8.17b43)", "sphinx (>=4.1)", "sphinx-autodoc-typehints (>=1.12)"]
-testing = ["covdefaults (>=1.2.0)", "coverage (>=4)", "pytest (>=4)", "pytest-cov", "pytest-timeout (>=1.4.2)"]
-
 [[package]]
 name = "flake8"
 version = "3.9.2"
@@ -1083,14 +1063,6 @@ category = "dev"
 optional = false
 python-versions = "*"
 
-[[package]]
-name = "toml"
-version = "0.10.2"
-description = "Python Library for Tom's Obvious, Minimal Language"
-category = "dev"
-optional = false
-python-versions = ">=2.6, !=3.0.*, !=3.1.*, !=3.2.*"
-
 [[package]]
 name = "tomli"
 version = "1.2.3"
@@ -1099,29 +1071,6 @@ category = "dev"
 optional = false
 python-versions = ">=3.6"
 
-[[package]]
-name = "tox"
-version = "3.25.1"
-description = "tox is a generic virtualenv management and test command line tool"
-category = "dev"
-optional = false
-python-versions = "!=3.0.*,!=3.1.*,!=3.2.*,!=3.3.*,!=3.4.*,>=2.7"
-
-[package.dependencies]
-colorama = {version = ">=0.4.1", markers = "platform_system == \"Windows\""}
-filelock = ">=3.0.0"
-importlib-metadata = {version = ">=0.12", markers = "python_version < \"3.8\""}
-packaging = ">=14"
-pluggy = ">=0.12.0"
-py = ">=1.4.17"
-six = ">=1.14.0"
-toml = ">=0.9.4"
-virtualenv = ">=16.0.0,<20.0.0 || >20.0.0,<20.0.1 || >20.0.1,<20.0.2 || >20.0.2,<20.0.3 || >20.0.3,<20.0.4 || >20.0.4,<20.0.5 || >20.0.5,<20.0.6 || >20.0.6,<20.0.7 || >20.0.7"
-
-[package.extras]
-docs = ["pygments-github-lexers (>=0.0.5)", "sphinx (>=2.0.0)", "sphinxcontrib-autoprogram (>=0.1.5)", "towncrier (>=18.5.0)"]
-testing = ["flaky (>=3.4.0)", "freezegun (>=0.3.11)", "pytest (>=4.0.0)", "pytest-cov (>=2.5.1)", "pytest-mock (>=1.10.0)", "pytest-randomly (>=1.0.0)", "psutil (>=5.6.1)", "pathlib2 (>=2.3.3)"]
-
 [[package]]
 name = "typed-ast"
 version = "1.4.3"
@@ -1179,37 +1128,36 @@ secure = ["pyOpenSSL (>=0.14)", "cryptography (>=1.3.4)", "idna (>=2.0.0)", "cer
 socks = ["PySocks (>=1.5.6,!=1.5.7,<2.0)"]
 
 [[package]]
-name = "virtualenv"
-version = "20.13.0"
-description = "Virtual Python Environment builder"
+name = "viztracer"
+version = "0.15.3"
+description = "A debugging and profiling tool that can trace and visualize python code execution"
 category = "dev"
 optional = false
-python-versions = "!=3.0.*,!=3.1.*,!=3.2.*,!=3.3.*,!=3.4.*,>=2.7"
+python-versions = ">=3.6"
 
 [package.dependencies]
-distlib = ">=0.3.1,<1"
-filelock = ">=3.2,<4"
-importlib-metadata = {version = ">=0.12", markers = "python_version < \"3.8\""}
-platformdirs = ">=2,<3"
-six = ">=1.9.0,<2"
+objprint = ">=0.1.3"
 
 [package.extras]
-docs = ["proselint (>=0.10.2)", "sphinx (>=3)", "sphinx-argparse (>=0.2.5)", "sphinx-rtd-theme (>=0.4.3)", "towncrier (>=21.3)"]
-testing = ["coverage (>=4)", "coverage-enable-subprocess (>=1)", "flaky (>=3)", "pytest (>=4)", "pytest-env (>=0.6.2)", "pytest-freezegun (>=0.4.1)", "pytest-mock (>=2)", "pytest-randomly (>=1)", "pytest-timeout (>=1)", "packaging (>=20.0)"]
+full = ["rich", "orjson"]
 
 [[package]]
-name = "viztracer"
-version = "0.15.3"
-description = "A debugging and profiling tool that can trace and visualize python code execution"
+name = "xdoctest"
+version = "1.0.0"
+description = "A rewrite of the builtin doctest module"
 category = "dev"
 optional = false
-python-versions = ">=3.6"
+python-versions = "*"
 
 [package.dependencies]
-objprint = ">=0.1.3"
+six = "*"
 
 [package.extras]
-full = ["rich", "orjson"]
+all = ["ipython", "ipython", "pygments", "pygments", "attrs", "cmake", "codecov", "colorama", "debugpy", "ipykernel", "ipykernel", "jedi", "jinja2", "jupyter-client", "jupyter-client", "jupyter-core", "nbconvert", "ninja", "pybind11", "pytest-cov", "pytest-cov", "pytest-cov", "pytest-cov", "pytest", "pytest", "pytest", "pytest", "pytest", "pytest", "scikit-build", "six", "typing"]
+jupyter = ["ipython", "ipython", "attrs", "debugpy", "ipykernel", "ipykernel", "jedi", "jinja2", "jupyter-client", "jupyter-client", "jupyter-core", "nbconvert"]
+optional = ["ipython", "ipython", "pygments", "pygments", "attrs", "colorama", "debugpy", "ipykernel", "ipykernel", "jedi", "jinja2", "jupyter-client", "jupyter-client", "jupyter-core", "nbconvert"]
+colors = ["pygments", "pygments", "colorama"]
+tests = ["cmake", "codecov", "ninja", "pybind11", "pytest-cov", "pytest-cov", "pytest-cov", "pytest-cov", "pytest", "pytest", "pytest", "pytest", "pytest", "pytest", "scikit-build", "typing"]
 
 [[package]]
 name = "zipp"
@@ -1229,7 +1177,7 @@ docs = ["sphinx", "sphinx-rtd-theme", "sphinx-copybutton", "myst-parser"]
 [metadata]
 lock-version = "1.1"
 python-versions = "<3.11,>=3.7.1"
-content-hash = "147d7faee6e61be7bd0bbcd905d44bad509b7ed2f3b7917d965141d1f87fd559"
+content-hash = "324f962f66d674b1fa00bf8ab64be671585e3ac6741352649228826b0ec1e2e9"
 
 [metadata.files]
 alabaster = [
@@ -1439,18 +1387,10 @@ decorator = [
     {file = "decorator-5.1.1-py3-none-any.whl", hash = "sha256:b8c3f85900b9dc423225913c5aace94729fe1fa9763b38939a95226f02d37186"},
     {file = "decorator-5.1.1.tar.gz", hash = "sha256:637996211036b6385ef91435e4fae22989472f9d571faba8927ba8253acbc330"},
 ]
-distlib = [
-    {file = "distlib-0.3.4-py2.py3-none-any.whl", hash = "sha256:6564fe0a8f51e734df6333d08b8b94d4ea8ee6b99b5ed50613f731fd4089f34b"},
-    {file = "distlib-0.3.4.zip", hash = "sha256:e4b58818180336dc9c529bfb9a0b58728ffc09ad92027a3f30b7cd91e3458579"},
-]
 docutils = [
     {file = "docutils-0.16-py2.py3-none-any.whl", hash = "sha256:0c5b78adfbf7762415433f5515cd5c9e762339e23369dbe8000d84a4bf4ab3af"},
     {file = "docutils-0.16.tar.gz", hash = "sha256:c2de3a60e9e7d07be26b7f2b00ca0309c207e06c100f9cc2a94931fc75a478fc"},
 ]
-filelock = [
-    {file = "filelock-3.4.1-py3-none-any.whl", hash = "sha256:a4bc51381e01502a30e9f06dd4fa19a1712eab852b6fb0f84fd7cce0793d8ca3"},
-    {file = "filelock-3.4.1.tar.gz", hash = "sha256:0f12f552b42b5bf60dba233710bf71337d35494fc8bdd4fd6d9f6d082ad45e06"},
-]
 flake8 = [
     {file = "flake8-3.9.2-py2.py3-none-any.whl", hash = "sha256:bf8fd333346d844f616e8d47905ef3a3384edae6b4e9beb0c5101e25e3110907"},
     {file = "flake8-3.9.2.tar.gz", hash = "sha256:07528381786f2a6237b061f6e96610a4167b226cb926e2aa2b6b1d78057c576b"},
@@ -2038,18 +1978,10 @@ text-unidecode = [
     {file = "text-unidecode-1.3.tar.gz", hash = "sha256:bad6603bb14d279193107714b288be206cac565dfa49aa5b105294dd5c4aab93"},
     {file = "text_unidecode-1.3-py2.py3-none-any.whl", hash = "sha256:1311f10e8b895935241623731c2ba64f4c455287888b18189350b67134a822e8"},
 ]
-toml = [
-    {file = "toml-0.10.2-py2.py3-none-any.whl", hash = "sha256:806143ae5bfb6a3c6e736a764057db0e6a0e05e338b5630894a5f779cabb4f9b"},
-    {file = "toml-0.10.2.tar.gz", hash = "sha256:b3bda1d108d5dd99f4a20d24d9c348e91c4db7ab1b749200bded2f839ccbe68f"},
-]
 tomli = [
     {file = "tomli-1.2.3-py3-none-any.whl", hash = "sha256:e3069e4be3ead9668e21cb9b074cd948f7b3113fd9c8bba083f48247aab8b11c"},
     {file = "tomli-1.2.3.tar.gz", hash = "sha256:05b6166bff487dc068d322585c7ea4ef78deed501cc124060e0f238e89a9231f"},
 ]
-tox = [
-    {file = "tox-3.25.1-py2.py3-none-any.whl", hash = "sha256:c38e15f4733683a9cc0129fba078633e07eb0961f550a010ada879e95fb32632"},
-    {file = "tox-3.25.1.tar.gz", hash = "sha256:c138327815f53bc6da4fe56baec5f25f00622ae69ef3fe4e1e385720e22486f9"},
-]
 typed-ast = [
     {file = "typed_ast-1.4.3-cp35-cp35m-manylinux1_i686.whl", hash = "sha256:2068531575a125b87a41802130fa7e29f26c09a2833fea68d9a40cf33902eba6"},
     {file = "typed_ast-1.4.3-cp35-cp35m-manylinux1_x86_64.whl", hash = "sha256:c907f561b1e83e93fad565bac5ba9c22d96a54e7ea0267c708bffe863cbe4075"},
@@ -2102,10 +2034,6 @@ urllib3 = [
     {file = "urllib3-1.26.8-py2.py3-none-any.whl", hash = "sha256:000ca7f471a233c2251c6c7023ee85305721bfdf18621ebff4fd17a8653427ed"},
     {file = "urllib3-1.26.8.tar.gz", hash = "sha256:0e7c33d9a63e7ddfcb86780aac87befc2fbddf46c58dbb487e0855f7ceec283c"},
 ]
-virtualenv = [
-    {file = "virtualenv-20.13.0-py2.py3-none-any.whl", hash = "sha256:339f16c4a86b44240ba7223d0f93a7887c3ca04b5f9c8129da7958447d079b09"},
-    {file = "virtualenv-20.13.0.tar.gz", hash = "sha256:d8458cf8d59d0ea495ad9b34c2599487f8a7772d796f9910858376d1600dd2dd"},
-]
 viztracer = [
     {file = "viztracer-0.15.3-cp310-cp310-macosx_10_15_x86_64.whl", hash = "sha256:1ae9c70ea45f6d56faab89f46e387e31c5e20484b024cbf8cb4542140f131060"},
     {file = "viztracer-0.15.3-cp310-cp310-manylinux_2_17_aarch64.manylinux2014_aarch64.whl", hash = "sha256:5799fc9c284047030f6de1448ef9681782ffb49f4e54ce3f9d890dd214436991"},
@@ -2144,6 +2072,11 @@ viztracer = [
     {file = "viztracer-0.15.3-cp39-cp39-win_amd64.whl", hash = "sha256:4280b59d699ed5aec175eb3c825e494779b6501d59cc6281195efe4ab4bfa812"},
     {file = "viztracer-0.15.3.tar.gz", hash = "sha256:f28de150304c300b27b3335993e0bdc47f5a7ba7b6f8c43dc54c4e74efa32cd6"},
 ]
+xdoctest = [
+    {file = "xdoctest-1.0.0-py2-none-any.whl", hash = "sha256:0b0b5958e0ac0a28c5496f96b7f0adbeb0ea7e0c0a227de1ce3bc79ddb1a4f00"},
+    {file = "xdoctest-1.0.0-py3-none-any.whl", hash = "sha256:76f44dc74515ff4bdf3cc3e91a2e408cf5699cfa03367634efaadf138c7b132d"},
+    {file = "xdoctest-1.0.0.tar.gz", hash = "sha256:7ebba7e71457e6e7cf86c463699575e52b1c9cc32ee2ee5e72256d6cd3aaeb2d"},
+]
 zipp = [
     {file = "zipp-3.6.0-py3-none-any.whl", hash = "sha256:9fe5ea21568a0a70e50f273397638d39b03353731e6cbbb3fd8502a33fec40bc"},
     {file = "zipp-3.6.0.tar.gz", hash = "sha256:71c644c5369f4a6e07636f0aa966270449561fcea2e3d6747b8d23efaa9d7832"},
diff --git a/pyproject.toml b/pyproject.toml
index 8c8b2eb32..ad3afab95 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -56,13 +56,13 @@ docs = ["sphinx", "sphinx-rtd-theme", "sphinx-copybutton", "myst-parser"]
 [tool.poetry.dev-dependencies]
 # snowflake-connector-python = "2.0.4" # Removed: Too many version conflicts!
 pytest = "^7.1.2"
+xdoctest = "^1.0.0"
 mypy = "^0.961"
 cookiecutter = "^2.1.1"
 PyYAML = "^6.0"
 pyarrow = "^8.0.0"
 pandas = ">=1.2.0"
 numpy = ">=1.20.0"
-tox = "^3.25.1"
 freezegun = "^1.2.1"
 viztracer = "^0.15.3"
 requests-mock = "^1.9.3"
@@ -104,6 +104,25 @@ version_files = [
     "cookiecutter/target-template/{{cookiecutter.target_id}}/pyproject.toml:singer-sdk",
 ]
 
+[tool.coverage.run]
+source = ["singer_sdk"]
+omit = [
+    "tests/*",
+    "samples/*",
+    "singer_sdk/helpers/_compat.py",
+]
+
+[tool.coverage.report]
+exclude_lines = [
+    "pragma: no cover",
+    "def __repr__",
+    "raise AssertionError",
+    "raise NotImplementedError",
+    "if __name__ == .__main__.:",
+    '''class .*\bProtocol\):''',
+]
+fail_under = 85
+
 [build-system]
 requires = ["poetry-core>=1.0.0"]
 build-backend = "poetry.core.masonry.api"
diff --git a/tox.ini b/tox.ini
index cf749cfa2..68c5c5bf3 100644
--- a/tox.ini
+++ b/tox.ini
@@ -66,37 +66,3 @@ commands =
 [testenv:coverage_artifact]
 commands =
     poetry run coverage {posargs:xml}
-
-[flake8]
-ignore = W503, C901, ANN101
-max-line-length = 88
-exclude = cookiecutter
-per-file-ignores =
-    # Don't require docstrings or type annotations in tests
-    tests/*:D100,D102,D103,DAR,ANN
-    # Don't require docstrings conventions or type annotations in SDK samples
-    samples/*:ANN,DAR
-    # Don't require docstrings conventions or type annotations in private modules
-    singer_sdk/helpers/_*.py:ANN,DAR,D105
-    # Don't require docstrings conventions in "meta" code
-    singer_sdk/helpers/_classproperty.py:D105
-max-complexity = 10
-docstring-convention = google
-allow-star-arg-any = true
-
-[coverage:run]
-source = singer_sdk
-omit =
-    tests/*
-    samples/*
-    singer_sdk/helpers/_compat.py
-
-[coverage:report]
-exclude_lines =
-    pragma: no cover
-    def __repr__
-    raise AssertionError
-    raise NotImplementedError
-    if __name__ == .__main__.:
-    class .*\bProtocol\):
-fail_under = 85