diff --git a/.github/workflows/msys.yml b/.github/workflows/msys.yml
index 84e202e69..f6f787648 100644
--- a/.github/workflows/msys.yml
+++ b/.github/workflows/msys.yml
@@ -25,6 +25,11 @@ jobs:
             mingw-w64-x86_64-ninja
             mingw-w64-x86_64-meson
             mingw-w64-x86_64-cmake
+            mingw-w64-x86_64-python-pip
+
+      - name: Irrational Python things
+        run: |
+          MSYSTEM= pip install --upgrade certifi
 
       - name: Build Aegisub
         run: |