diff --git a/.github/workflows/tests.yml b/.github/workflows/tests.yml
index e019ec50..dfb28b82 100644
--- a/.github/workflows/tests.yml
+++ b/.github/workflows/tests.yml
@@ -61,12 +61,24 @@ jobs:
 
       - name: Install and configure Poetry
         uses: snok/install-poetry@v1
+        if: !startswith(matrix.python-version, 'pypy') || matrix.os != 'windows-latest'
         with:
           version: 1.1.11
           virtualenvs-create: true
           virtualenvs-in-project: true
           installer-parallel: true
 
+      - name: Install and configure Poetry (PyPy on Windows)
+        if: startswith(matrix.python-version, 'pypy') && matrix.os == 'windows-latest'
+        env:
+          POETRY_VERSION: 1.1.11
+        run: |
+          set -eu
+          pip install 'poetry==$POETRY_VERSION'
+          poetry config virtualenvs.create true
+          poetry config virtualenvs.in-project true
+          poetry config installer.parallel true
+
       - name: Setup redis
         if: ${{ matrix.os != 'windows-latest' }}
         uses: shogo82148/actions-setup-redis@v1