diff --git a/.github/workflows/ci.yaml b/.github/workflows/ci.yaml
index 23d16ffadb9..f33671d5391 100644
--- a/.github/workflows/ci.yaml
+++ b/.github/workflows/ci.yaml
@@ -294,8 +294,7 @@ jobs:
           mkdir site-packages
           target/release/rustpython --install-pip ensurepip --user
           target/release/rustpython -m pip install six
-      - if: runner.os != 'Windows'
-        name: Check that ensurepip succeeds.
+      - name: Check that ensurepip succeeds.
         run: |
           target/release/rustpython -m ensurepip
           target/release/rustpython -c "import pip"
diff --git a/Lib/ensurepip/_bundled/pip-25.2-py3-none-any.whl b/Lib/ensurepip/_bundled/pip-25.2-py3-none-any.whl
index e14bb3f37c0..4db7e720718 100644
Binary files a/Lib/ensurepip/_bundled/pip-25.2-py3-none-any.whl and b/Lib/ensurepip/_bundled/pip-25.2-py3-none-any.whl differ