diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index f98f0afed..86f356af8 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -218,6 +218,12 @@ jobs:
 
       - uses: actions/checkout@v3
 
+      # NOTE(aznashwan): starting with Golang 1.21, the windows-2019 GitHub runner's
+      # builtin MinGW version leads to DLL loading errors during runtime.
+      - name: Upgrade MinGW on Windows 2019
+        if: matrix.os == 'windows-2019'
+        run: choco upgrade mingw
+
       - name: Make
         run: |
           make build
@@ -269,6 +275,12 @@ jobs:
 
       - run: script/setup/install-dev-tools
 
+      # NOTE(aznashwan): starting with Golang 1.21, the windows-2019 GitHub runner's
+      # builtin MinGW version leads to DLL loading errors during runtime.
+      - name: Upgrade MinGW on Windows 2019
+        if: matrix.os == 'windows-2019'
+        run: choco upgrade mingw
+
       - name: Binaries
         env:
           CGO_ENABLED: 1