[ci] Fix broken Windows PyPy tests (#17347)

Workaround for https://github.com/actions/setup-python/issues/1348

Authored by: bashonly

.github/workflows/challenge-tests.yml

@@ -43,24 +43,29 @@ jobs:
     - uses: actions/checkout@9c091bb21b7c1c1d1991bb908d89e4e9dddfe3e0  # v7.0.0
       with:
         persist-credentials: false
+
     - name: Set up Python ${{ matrix.python-version }}
       uses: actions/setup-python@ece7cb06caefa5fff74198d8649806c4678c61a1  # v6.3.0
       with:
         python-version: ${{ matrix.python-version }}
         allow-prereleases: true
+
     - name: Install Deno
       uses: denoland/setup-deno@667a34cdef165d8d2b2e98dde39547c9daac7282  # v2.0.4
       with:
         deno-version: '2.3.0'  # minimum supported version
+
     - name: Install Bun
       uses: oven-sh/setup-bun@0c5077e51419868618aeaa5fe8019c62421857d6  # v2.2.0
       with:
         bun-version: '1.2.11'  # minimum supported version
         no-cache: true
+
     - name: Install Node
       uses: actions/setup-node@48b55a011bda9f5d6aeb4c2d9c7362e8dae4041e  # v6.4.0
       with:
         node-version: '22.0'  # minimum supported version
+
     - name: Install QuickJS (Linux)
       if: matrix.os == 'ubuntu-latest'
       shell: bash
@@ -68,6 +73,7 @@ jobs:
         wget "https://bellard.org/quickjs/binary_releases/quickjs-linux-x86_64-${QJS_VERSION}.zip" -O quickjs.zip
         unzip quickjs.zip qjs
         sudo install qjs /usr/local/bin/qjs
+
     - name: Install QuickJS (Windows)
       if: matrix.os == 'windows-latest'
       shell: pwsh
@@ -76,12 +82,22 @@ jobs:
         $PSNativeCommandUseErrorActionPreference = $true
         Invoke-WebRequest "https://bellard.org/quickjs/binary_releases/quickjs-win-x86_64-${Env:QJS_VERSION}.zip" -OutFile quickjs.zip
         unzip quickjs.zip
-    - name: Install test requirements
+
-      shell: bash
+    - name: Install test requirements (cpython)
+      if: ${{ !startsWith(matrix.python-version, 'pypy') }}
       run: |
         python -m pip install -U --require-hashes -r "bundle/requirements/pip.txt"
         python -m pip install -U --require-hashes -r "bundle/requirements/test.txt"
         python -m pip install -U --require-hashes -r "bundle/requirements/default.txt"
+
+    - name: Install test requirements (PyPy)
+      if: ${{ startsWith(matrix.python-version, 'pypy') }}
+      run: |
+        # Upgrading/downgrading pip on Windows with actions/setup-python's PyPy can cause breakage
+        # See https://github.com/actions/setup-python/issues/1348
+        python -m pip install -U --require-hashes -r "bundle/requirements/test.txt"
+        python -m pip install -U --require-hashes -r "bundle/requirements/default.txt"
+
     - name: Run tests
       timeout-minutes: 15
       shell: bash

.github/workflows/core.yml

@@ -85,7 +85,8 @@ jobs:
     - name: Install test requirements (PyPy)
       if: ${{ startsWith(matrix.python-version, 'pypy') }}
       run: |
-        python -m pip install -U --require-hashes -r "bundle/requirements/pip.txt"
+        # Upgrading/downgrading pip on Windows with actions/setup-python's PyPy can cause breakage
+        # See https://github.com/actions/setup-python/issues/1348
         python -m pip install -U --require-hashes -r "bundle/requirements/test.txt"
         python -m pip install -U --require-hashes -r "bundle/requirements/default.txt"