diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index fba12055..e069e0a1 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -149,7 +149,7 @@ jobs:
         ./linux-container-ci.sh ${{ env.BUILDER_VERSION }} aws-crt-${{ env.LINUX_BASE_IMAGE }} build downstream -p ${{ env.PACKAGE_NAME }}
 
   windows:
-    runs-on: windows-2022 # latest
+    runs-on: windows-2025 # latest
     steps:
     - uses: aws-actions/configure-aws-credentials@v4
       with:
@@ -160,8 +160,8 @@ jobs:
         python -c "from urllib.request import urlretrieve; urlretrieve('${{ env.BUILDER_HOST }}/${{ env.BUILDER_SOURCE }}/${{ env.BUILDER_VERSION }}/builder.pyz?run=${{ env.RUN }}', 'builder.pyz')"
         python builder.pyz build -p ${{ env.PACKAGE_NAME }}
 
-  windows-vc14:
-    runs-on: windows-2019 # windows-2019 is last env with Visual Studio 2015 (v14.0)
+  windows-vc17:
+    runs-on: windows-2025 # latest
     strategy:
       matrix:
         arch: [x86, x64]
@@ -173,10 +173,10 @@ jobs:
     - name: Build ${{ env.PACKAGE_NAME }} + consumers
       run: |
         python -c "from urllib.request import urlretrieve; urlretrieve('${{ env.BUILDER_HOST }}/${{ env.BUILDER_SOURCE }}/${{ env.BUILDER_VERSION }}/builder.pyz?run=${{ env.RUN }}', 'builder.pyz')"
-        python builder.pyz build -p ${{ env.PACKAGE_NAME }} --target windows-${{ matrix.arch }} --compiler msvc-14
+        python builder.pyz build -p ${{ env.PACKAGE_NAME }} --target windows-${{ matrix.arch }} --compiler msvc-17
 
   windows-shared-libs:
-    runs-on: windows-2022 # latest
+    runs-on: windows-2025 # latest
     steps:
     - uses: aws-actions/configure-aws-credentials@v4
       with:
@@ -188,7 +188,7 @@ jobs:
         python builder.pyz build -p ${{ env.PACKAGE_NAME }} --cmake-extra=-DBUILD_SHARED_LIBS=ON
 
   windows-app-verifier:
-    runs-on: windows-2022 # latest
+    runs-on: windows-2025 # latest
     steps:
     - uses: aws-actions/configure-aws-credentials@v4
       with:
@@ -267,7 +267,7 @@ jobs:
         python3 builder.pyz build -p aws-c-http --cmake-extra=-DENABLE_LOCALHOST_INTEGRATION_TESTS=ON --cmake-extra=-DAWS_USE_APPLE_NETWORK_FRAMEWORK=${{ matrix.eventloop == 'dispatch_queue' && 'ON' || 'OFF' }} --config Debug
 
   localhost-test-win:
-    runs-on: windows-2022 # latest
+    runs-on: windows-2025 # latest
     steps:
     - uses: aws-actions/configure-aws-credentials@v4
       with: