diff --git a/.github/workflows/windows.yml b/.github/workflows/windows.yml
index 63089b951..339c63723 100644
--- a/.github/workflows/windows.yml
+++ b/.github/workflows/windows.yml
@@ -20,6 +20,17 @@ jobs:
         uses: ruby/setup-ruby@v1
         with:
           ruby-version: ${{ matrix.ruby }}
+
+      # ucrt and mswin have the dev version Ruby.
+      # It introduce checksum mismatches for bundled gems. So remove them before `bundle install`
+      - name: Purge gem caches
+        run: |
+          ruby -e '
+            exit if "${{ matrix.ruby }}" != "ucrt" && "${{ matrix.ruby }}" != "mswin"
+            bundled_gems = Dir.glob("D:/ruby-${{ matrix.ruby }}/lib/ruby/gems/*/cache/*.gem")
+              .map { |path| File.basename(path, ".gem")[/^(.+)-[^-]+$/, 1] }
+            system "gem uninstall #{bundled_gems.join(" ")}", exception: true
+          '
       - name: bundle install
         run: |
           bundle config set without profilers libs
diff --git a/Gemfile.lock b/Gemfile.lock
index 83608be8f..07475164d 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -196,4 +196,4 @@ DEPENDENCIES
   test-unit
 
 BUNDLED WITH
-   2.5.16
+   2.6.3
diff --git a/steep/Gemfile.lock b/steep/Gemfile.lock
index 4e1645b41..c7587ef85 100644
--- a/steep/Gemfile.lock
+++ b/steep/Gemfile.lock
@@ -76,4 +76,4 @@ DEPENDENCIES
   steep (~> 1.9.2)
 
 BUNDLED WITH
-   2.5.16
+   2.6.3