diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index 071401556b..ed5ca0575d 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -283,21 +283,18 @@ jobs:
             exit $LASTEXITCODE
           }
 
+      # needs to be a separate step since terminal reload is required to bring in new env variables and PATH
+      - name: Upgrade Chocolaty
+        shell: powershell
+        run: |
+          choco upgrade -y chocolatey 2>&1
+
       - name: Install mingw
         shell: powershell
         run: |
           $VerbosePreference = 'Continue'
           # dont set $ErrorActionPreference since we want to allow choco install to fail later on
 
-          Write-Output '::group::Update chocolaty'
-          choco upgrade -y chocolatey
-          Write-Output '::endgroup::'
-
-          if ( $LASTEXITCODE ) {
-            Write-Output '::error::Could not update chocolatey.'
-            exit $LASTEXITCODE
-          }
-
           Write-Output 'Install mingw'
           # Install sometimes fails when downloading mingw zip from source-forge with:
           #  "ERROR: The remote file either doesn't exist, is unauthorized, or is forbidden for url"
@@ -314,7 +311,7 @@ jobs:
               Sleep -Seconds 60
             }
 
-            choco install -y --no-progress --stop-on-first-failure --force mingw --allow-downgrade --version 10.2.0
+            choco install -y --no-progress --stop-on-first-failure --force mingw --allow-downgrade --version 10.3.0
             Write-Output '::endgroup::'
             if ( -not $LASTEXITCODE ) {
               Write-Output "Attempt $i succeeded (exit code: $LASTEXITCODE)"
@@ -328,6 +325,9 @@ jobs:
             exit $LASTEXITCODE
           }
 
+          # verify mingw32-make was installed
+          Get-Command -CommandType Application -ErrorAction Stop mingw32-make.exe
+
       - name: Build binaries
         shell: bash
         working-directory: src/github.com/containerd/containerd