diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index f6ab5a259..95999acf0 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -291,6 +291,31 @@ jobs:
       - name: "Validate global Python install"
         run: pyston scripts/check_system_python.py --uv ./uv
 
+  system-test-alpine:
+    needs: build-binary-linux
+    name: "check system | alpine"
+    runs-on: ubuntu-latest
+    container: alpine:latest
+    steps:
+      - uses: actions/checkout@v4
+
+      - name: "Install Python"
+        run: apk add --update --no-cache python3 py3-pip
+
+      - name: "Download binary"
+        uses: actions/download-artifact@v4
+        with:
+          name: uv-linux-${{ github.sha }}
+
+      - name: "Prepare binary"
+        run: chmod +x ./uv
+
+      - name: "Print Python path"
+        run: echo $(which python3)
+
+      - name: "Validate global Python install"
+        run: python3 scripts/check_system_python.py --uv ./uv --externally-managed
+
   system-test-macos:
     needs: build-binary-macos-aarch64
     name: "check system | python on macos"
@@ -383,7 +408,7 @@ jobs:
         run: py -3.9 ./scripts/check_system_python.py --uv ./uv.exe
 
   system-test-pyenv:
-    needs: build-binary-windows
+    needs: build-binary-linux
     name: "check system | python via pyenv"
     runs-on: ubuntu-latest
     steps:
diff --git a/scripts/check_system_python.py b/scripts/check_system_python.py
index a4ba8bf6b..a29c00ba3 100755
--- a/scripts/check_system_python.py
+++ b/scripts/check_system_python.py
@@ -14,9 +14,17 @@ if __name__ == "__main__":
 
     parser = argparse.ArgumentParser(description="Check a Python interpreter.")
     parser.add_argument("--uv", help="Path to a uv binary.")
+    parser.add_argument(
+        "--externally-managed",
+        action="store_true",
+        help="Set if the Python installation has an EXTERNALLY-MANAGED marker.",
+    )
     args = parser.parse_args()
 
     uv: str = os.path.abspath(args.uv) if args.uv else "uv"
+    allow_externally_managed = (
+        ["--break-system-packages"] if args.externally_managed else []
+    )
 
     # Create a temporary directory.
     with tempfile.TemporaryDirectory() as temp_dir:
@@ -32,7 +40,7 @@ if __name__ == "__main__":
         # Install the package (`pylint`).
         logging.info("Installing the package `pylint`.")
         subprocess.run(
-            [uv, "pip", "install", "pylint", "--system"],
+            [uv, "pip", "install", "pylint", "--system"] + allow_externally_managed,
             cwd=temp_dir,
             check=True,
         )
@@ -57,7 +65,7 @@ if __name__ == "__main__":
         # Uninstall the package (`pylint`).
         logging.info("Uninstalling the package `pylint`.")
         subprocess.run(
-            [uv, "pip", "uninstall", "pylint", "--system"],
+            [uv, "pip", "uninstall", "pylint", "--system"] + allow_externally_managed,
             cwd=temp_dir,
             check=True,
         )