diff --git a/scripts/azure-pipelines/windows/azure-pipelines.yml b/scripts/azure-pipelines/windows/azure-pipelines.yml
index b9bf49e227a680..f680ac2056d000 100644
--- a/scripts/azure-pipelines/windows/azure-pipelines.yml
+++ b/scripts/azure-pipelines/windows/azure-pipelines.yml
@@ -26,7 +26,7 @@ jobs:
   - script: .\bootstrap-vcpkg.bat
     displayName: 'Build vcpkg'
   - task: CmdLine@2
-    displayName: "Build vcpkg with CMake and Run Tests"
+    displayName: "Build vcpkg with CMake, with older VS, and Run Tests"
     condition: eq('${{ parameters.triplet }}', 'x86-windows')
     inputs:
       script: |
@@ -39,6 +39,10 @@ jobs:
         cmake.exe -G Ninja -DCMAKE_BUILD_TYPE=Debug -DBUILD_TESTING=ON -DVCPKG_DEVELOPMENT_WARNINGS=ON -DVCPKG_WARNINGS_AS_ERRORS=ON -DVCPKG_BUILD_FUZZING=ON -B build.x86.debug -S toolsrc
         ninja.exe -C build.x86.debug
         build.x86.debug\vcpkg-test.exe
+        cmake -G "Visual Studio 16 2019" -A Win32 -T v140 -DBUILD_TESTING=OFF -DVCPKG_DEVELOPMENT_WARNINGS=OFF -DVCPKG_WARNINGS_AS_ERRORS=ON -DVCPKG_BUILD_FUZZING=OFF -B build.x86.vs2015 -S toolsrc
+        cmake --build build.x86.vs2015
+        cmake -G "Visual Studio 16 2019" -A Win32 -T v141 -DBUILD_TESTING=OFF -DVCPKG_DEVELOPMENT_WARNINGS=OFF -DVCPKG_WARNINGS_AS_ERRORS=ON -DVCPKG_BUILD_FUZZING=OFF -B build.x86.vs2017 -S toolsrc
+        cmake --build build.x86.vs2017
       failOnStderr: true
   - task: PowerShell@2
     displayName: 'Run vcpkg end-to-end tests'