diff --git a/template/.github/workflows/ci.yaml.jinja b/template/.github/workflows/ci.yaml.jinja
index 6a19c0c2..8ee529b1 100644
--- a/template/.github/workflows/ci.yaml.jinja
+++ b/template/.github/workflows/ci.yaml.jinja
@@ -77,7 +77,13 @@ jobs:
     timeout-minutes: {% endraw %}{{ gha_medium_timeout_minutes }}{% raw %}
     env:
       UV_PYTHON: ${{ matrix.python-version }}
-    steps:
+    steps:{% endraw %}{% if use_windows_in_ci %}
+      - name: Allow long file paths
+        if: runner.os == 'Windows'
+        # Some tooling (e.g. vcrpy, syrupy) generates file names past the 260 character limit Windows
+        # defaults to. This has to happen before the checkout that writes those files.
+        run: git config --global core.longpaths true
+{% endif %}{% raw %}
       - name: Checkout code
         uses: actions/checkout@{% endraw %}{{ gha_checkout }}{% raw %}
 
@@ -170,7 +176,13 @@ jobs:
     env:
       UV_PYTHON: ${{ matrix.python-version }}
 
-    steps:
+    steps:{% endraw %}{% if use_windows_in_exe_ci %}
+      - name: Allow long file paths
+        if: runner.os == 'Windows'
+        # Some tooling (e.g. vcrpy, syrupy) generates file names past the 260 character limit Windows
+        # defaults to. This has to happen before the checkout that writes those files.
+        run: git config --global core.longpaths true
+{% endif %}{% raw %}
       - name: Checkout code
         uses: actions/checkout@{% endraw %}{{ gha_checkout }}{% raw %}
       - name: Install python tooling
diff --git a/template/.github/workflows/release.yaml.jinja b/template/.github/workflows/release.yaml.jinja
index b5341b68..dfb53f59 100644
--- a/template/.github/workflows/release.yaml.jinja
+++ b/template/.github/workflows/release.yaml.jinja
@@ -157,7 +157,13 @@ jobs:
     env:
       UV_PYTHON: ${{ matrix.python-version }}
 
-    steps:
+    steps:{% endraw %}{% if use_windows_in_ci %}
+      - name: Allow long file paths
+        if: runner.os == 'Windows'
+        # Some tooling (e.g. vcrpy, syrupy) generates file names past the 260 character limit Windows
+        # defaults to. This has to happen before the checkout that writes those files.
+        run: git config --global core.longpaths true
+{% endif %}{% raw %}
       - name: Checkout code
         uses: actions/checkout@{% endraw %}{{ gha_checkout }}{% raw %}
       - name: Setup python
@@ -313,7 +319,13 @@ jobs:
     env:
       UV_PYTHON: ${{ matrix.python-version }}
 
-    steps:
+    steps:{% endraw %}{% if use_windows_in_ci %}
+      - name: Allow long file paths
+        if: runner.os == 'Windows'
+        # Some tooling (e.g. vcrpy, syrupy) generates file names past the 260 character limit Windows
+        # defaults to. This has to happen before the checkout that writes those files.
+        run: git config --global core.longpaths true
+{% endif %}{% raw %}
       - name: Checkout code
         uses: actions/checkout@{% endraw %}{{ gha_checkout }}{% raw %}
       - name: Setup python
diff --git a/template/.github/workflows/{% if not deploy_as_executable %}publish.yaml{% endif %}.jinja b/template/.github/workflows/{% if not deploy_as_executable %}publish.yaml{% endif %}.jinja
index 3aee9a26..742ae764 100644
--- a/template/.github/workflows/{% if not deploy_as_executable %}publish.yaml{% endif %}.jinja	
+++ b/template/.github/workflows/{% if not deploy_as_executable %}publish.yaml{% endif %}.jinja	
@@ -67,7 +67,13 @@ jobs:
     env:
       UV_PYTHON: ${{ matrix.python-version }}
 
-    steps:
+    steps:{% endraw %}{% if use_windows_in_ci %}
+      - name: Allow long file paths
+        if: runner.os == 'Windows'
+        # Some tooling (e.g. vcrpy, syrupy) generates file names past the 260 character limit Windows
+        # defaults to. This has to happen before the checkout that writes those files.
+        run: git config --global core.longpaths true
+{% endif %}{% raw %}
       - name: Checkout code
         uses: actions/checkout@{% endraw %}{{ gha_checkout }}{% raw %}
 
@@ -180,7 +186,13 @@ jobs:
     env:
       UV_PYTHON: ${{ matrix.python-version }}
 
-    steps:
+    steps:{% endraw %}{% if use_windows_in_ci %}
+      - name: Allow long file paths
+        if: runner.os == 'Windows'
+        # Some tooling (e.g. vcrpy, syrupy) generates file names past the 260 character limit Windows
+        # defaults to. This has to happen before the checkout that writes those files.
+        run: git config --global core.longpaths true
+{% endif %}{% raw %}
       - name: Checkout code
         uses: actions/checkout@{% endraw %}{{ gha_checkout }}{% raw %}
       - name: Setup python
@@ -326,7 +338,13 @@ jobs:
     env:
       UV_PYTHON: ${{ matrix.python-version }}
 
-    steps:
+    steps:{% endraw %}{% if use_windows_in_ci %}
+      - name: Allow long file paths
+        if: runner.os == 'Windows'
+        # Some tooling (e.g. vcrpy, syrupy) generates file names past the 260 character limit Windows
+        # defaults to. This has to happen before the checkout that writes those files.
+        run: git config --global core.longpaths true
+{% endif %}{% raw %}
       - name: Checkout code
         uses: actions/checkout@{% endraw %}{{ gha_checkout }}{% raw %}
       - name: Setup python
diff --git a/template/.github/workflows/{% if not deploy_as_executable %}publish_to_staging.yaml{% endif %}.jinja b/template/.github/workflows/{% if not deploy_as_executable %}publish_to_staging.yaml{% endif %}.jinja
index 8d8aadc0..6a705008 100644
--- a/template/.github/workflows/{% if not deploy_as_executable %}publish_to_staging.yaml{% endif %}.jinja	
+++ b/template/.github/workflows/{% if not deploy_as_executable %}publish_to_staging.yaml{% endif %}.jinja	
@@ -41,7 +41,13 @@ jobs:
     env:
       UV_PYTHON: ${{ matrix.python-version }}
 
-    steps:
+    steps:{% endraw %}{% if use_windows_in_ci %}
+      - name: Allow long file paths
+        if: runner.os == 'Windows'
+        # Some tooling (e.g. vcrpy, syrupy) generates file names past the 260 character limit Windows
+        # defaults to. This has to happen before the checkout that writes those files.
+        run: git config --global core.longpaths true
+{% endif %}{% raw %}
       - name: Checkout code
         uses: actions/checkout@{% endraw %}{{ gha_checkout }}{% raw %}