diff --git a/.github/workflows/cookiecutter-e2e.yml b/.github/workflows/cookiecutter-e2e.yml
index 4dad4de4e..bd1e59290 100644
--- a/.github/workflows/cookiecutter-e2e.yml
+++ b/.github/workflows/cookiecutter-e2e.yml
@@ -18,32 +18,32 @@ env:
 
 jobs:
   lint:
-    name: Lint ${{ matrix.cookiecutter }}, Replay ${{ matrix.replay }} on ${{ matrix.python-version }} ${{ matrix.python-version }} / ${{ matrix.os }}
+    name: Cookiecutter E2E ${{ matrix.python-version }} ${{ matrix.python-version }} / ${{ matrix.os }}
     runs-on: ${{ matrix.os }}
     strategy:
       fail-fast: true
       matrix:
         include:
-          - { cookiecutter: "tap-template", replay: "tap-graphql-jwt.json", python-version: "3.9",  os: "ubuntu-latest" }
-          - { cookiecutter: "tap-template", replay: "tap-rest-api_key-github.json", python-version: "3.9",  os: "ubuntu-latest" }
-          - { cookiecutter: "tap-template", replay: "tap-rest-basic_auth.json", python-version: "3.9",  os: "ubuntu-latest" }
-          - { cookiecutter: "tap-template", replay: "tap-rest-bearer_token.json", python-version: "3.9",  os: "ubuntu-latest" }
-          - { cookiecutter: "tap-template", replay: "tap-rest-custom.json", python-version: "3.9",  os: "ubuntu-latest" }
-          - { cookiecutter: "tap-template", replay: "tap-rest-jwt.json", python-version: "3.9",  os: "ubuntu-latest" }
-          - { cookiecutter: "tap-template", replay: "tap-rest-oauth2.json", python-version: "3.9",  os: "ubuntu-latest" }
-          - { cookiecutter: "tap-template", replay: "tap-other-custom.json", python-version: "3.9",  os: "ubuntu-latest" }
-          - { cookiecutter: "tap-template", replay: "tap-sql-custom.json", python-version: "3.9",  os: "ubuntu-latest" }
-          - { cookiecutter: "target-template", replay: "target-per_record.json", python-version: "3.9",  os: "ubuntu-latest" }
+          - { python-version: "3.10",  os: "ubuntu-latest" }
 
     steps:
     - name: Check out the repository
-      uses: actions/checkout@v3.4.0
+      uses: actions/checkout@v3.3.0
 
+    - name: Install Poetry & Tox
+      env:
+        PIP_CONSTRAINT: .github/workflows/constraints.txt
+      run: |
+        pipx install poetry
+        poetry --version
+        pipx install tox
     - name: Setup Python ${{ matrix.python-version }}
       uses: actions/setup-python@v4.5.0
       with:
         python-version: ${{ matrix.python-version }}
         architecture: x64
+        cache: 'pip'
+        cache-dependency-path: 'poetry.lock'
 
     - name: Upgrade pip
       env:
@@ -52,32 +52,25 @@ jobs:
         pip install pip
         pip --version
 
-    - name: Install Poetry, Tox & Cookiecutter
+    - name: Install Nox
       env:
         PIP_CONSTRAINT: .github/workflows/constraints.txt
       run: |
-        pipx install poetry
-        pipx install cookiecutter
-        pipx install tox
+        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: Build cookiecutter project
-      env:
-        CC_TEMPLATE: cookiecutter/${{ matrix.cookiecutter }}
-        REPLAY_FILE: e2e-tests/cookiecutters/${{ matrix.replay }}
+    - name: Run Nox
       run: |
-        chmod +x ./e2e-tests/cookiecutters/test_cookiecutter.sh
-        ./e2e-tests/cookiecutters/test_cookiecutter.sh $CC_TEMPLATE $REPLAY_FILE 0
-
-    - uses: actions/upload-artifact@v3
+        nox --python=${{ matrix.python-version }} --session=test_cookiecutter
+    - name: Upload build artifacts
+      if: always()
+      uses: actions/upload-artifact@v3
       with:
-        name: ${{ matrix.replay }}
         path: |
-          ${{ env.CC_TEST_OUTPUT }}/
-          !${{ env.CC_TEST_OUTPUT }}/.mypy_cache/
-
-    - name: Run lint
-      env:
-        REPLAY_FILE: e2e-tests/cookiecutters/${{ matrix.replay }}
-      run: |
-        cd $CC_TEST_OUTPUT
-        poetry run tox -e lint
+          /tmp/tap-*
+          /tmp/target-*
+          !/tmp/tap-*/.mypy_cache/
+          !/tmp/target-*/.mypy_cache/
+          !/tmp/tap-*/.tox/
+          !/tmp/target-*/.tox/
diff --git a/e2e-tests/cookiecutters/test_cookiecutter.sh b/e2e-tests/cookiecutters/test_cookiecutter.sh
deleted file mode 100755
index a8a33afde..000000000
--- a/e2e-tests/cookiecutters/test_cookiecutter.sh
+++ /dev/null
@@ -1,58 +0,0 @@
-#!/bin/bash
-CC_BUILD_PATH=/tmp
-TAP_TEMPLATE=$(realpath $1)
-REPLAY_FILE=$(realpath $2)
-SDK_DIR=$(realpath $1/../..)
-CC_OUTPUT_DIR=$(basename $REPLAY_FILE .json) # name of replay file without .json
-RUN_LINT=${3:-1}
-
-usage() {
-    echo "test_cookiecutter.sh [tap_template] [replay_file.json]"
-    echo
-    echo "Uses the tap template to build an empty cookiecutter, and runs the lint task on the created test project"
-    echo ""
-    if [[ $# -eq 1 ]]; then
-        echo "ERROR: $1"
-    fi
-}
-
-if [[ ! -d $TAP_TEMPLATE ]]; then
-    usage "Tap template folder not found"
-    exit 1
-fi
-if [[ ! -f $REPLAY_FILE ]]; then
-    usage "Replay file not found"
-    exit 1
-fi
-
-CC_TEST_OUTPUT=$CC_BUILD_PATH/$CC_OUTPUT_DIR
-if [[ -d "$CC_TEST_OUTPUT" ]]; then
-    rm -fr "$CC_TEST_OUTPUT"
-fi
-
-if [[ -f $GITHUB_ENV ]]; then
-    echo CC_TEST_OUTPUT=$CC_BUILD_PATH/$CC_OUTPUT_DIR >> $GITHUB_ENV
-fi
-
-cookiecutter --replay-file $REPLAY_FILE $TAP_TEMPLATE -o $CC_BUILD_PATH &&
-    cd $CC_TEST_OUTPUT &&
-    pwd &&
-    sed -i.bak "s|singer-sdk =.*|singer-sdk = \{ path = \"$SDK_DIR\", develop = true \}|" pyproject.toml &&
-    poetry lock &&
-    poetry install
-
-if [[ $? -ne 0 ]]; then
-    exit $?
-fi
-
-# before linting, auto-fix what can be autofixed
-LIBRARY_NAME=$(ls * -d | egrep "tap|target")
-poetry run black $LIBRARY_NAME &&
-    poetry run isort $LIBRARY_NAME &&
-    poetry run flake8 $LIBRARY_NAME &&
-    poetry run mypy $LIBRARY_NAME
-##
-
-if [[ $RUN_LINT -eq 1 ]] && [[ $? -eq 0 ]]; then
-    poetry run tox -e lint
-fi
diff --git a/noxfile.py b/noxfile.py
index 995402f81..45c0c5974 100644
--- a/noxfile.py
+++ b/noxfile.py
@@ -2,9 +2,11 @@
 
 from __future__ import annotations
 
+import glob
 import os
 import shutil
 import sys
+import tempfile
 from pathlib import Path
 from textwrap import dedent
 
@@ -27,6 +29,7 @@
     "mypy",
     "tests",
     "doctest",
+    "test_cookiecutter",
 )
 test_dependencies = [
     "coverage[toml]",
@@ -170,3 +173,73 @@ def docs_serve(session: Session) -> None:
         shutil.rmtree(build_dir)
 
     session.run("sphinx-autobuild", *args)
+
+
+@nox.parametrize("replay_file_path", glob.glob("./e2e-tests/cookiecutters/*.json"))
+@session(python=main_python_version)
+def test_cookiecutter(session: Session, replay_file_path) -> None:
+    """Uses the tap template to build an empty cookiecutter.
+
+    Runs the lint task on the created test project.
+    """
+    args = session.posargs or ["1"]
+
+    cc_build_path = tempfile.gettempdir()
+    folder_base_path = "./cookiecutter"
+
+    target_folder = (
+        "tap-template"
+        if Path(replay_file_path).name.startswith("tap")
+        else "target-template"
+    )
+    tap_template = Path(folder_base_path + "/" + target_folder).resolve()
+    replay_file = Path(replay_file_path).resolve()
+
+    if not Path(tap_template).exists():
+        return
+
+    if not Path(replay_file).is_file():
+        return
+
+    sdk_dir = Path(Path(tap_template).parent).parent
+    cc_output_dir = Path(replay_file_path).name.replace(".json", "")
+    cc_test_output = cc_build_path + "/" + cc_output_dir
+
+    if Path(cc_test_output).exists():
+        session.run("rm", "-fr", cc_test_output, external=True)
+
+    session.install(".")
+    session.install("cookiecutter", "pythonsed")
+
+    session.run(
+        "cookiecutter",
+        "--replay-file",
+        str(replay_file),
+        str(tap_template),
+        "-o",
+        cc_build_path,
+    )
+    session.chdir(cc_test_output)
+
+    session.run(
+        "pythonsed",
+        "-i.bak",
+        's|singer-sdk =.*|singer-sdk = \\{ path = "'
+        + str(sdk_dir)
+        + '", develop = true \\}|',
+        "pyproject.toml",
+    )
+    session.run("poetry", "lock", external=True)
+    session.run("poetry", "install", external=True)
+
+    for path in glob.glob(f"{Path.cwd()}/*", recursive=True):
+        if Path(path).name.startswith("tap") or Path(
+            path,
+        ).name.startswith("target"):
+            library_name = Path(path).name
+
+    for argument in ["black", "isort", "flake8", "mypy"]:
+        session.run("poetry", "run", argument, library_name, external=True)
+
+    if int(args[0]) == 1:
+        session.run("poetry", "run", "tox", "-e", "lint", external=True)