diff --git a/eng/pipelines/daily-verification.yml b/eng/pipelines/daily-verification.yml
index 96dcea129..c7a332a67 100644
--- a/eng/pipelines/daily-verification.yml
+++ b/eng/pipelines/daily-verification.yml
@@ -3,8 +3,8 @@ jobs:
   - job:
     displayName: Daily vcpkg PR
     pool:
-      name: azsdk-pool-mms-win-2019-general
-      vmImage: MMS2019
+      name: azsdk-pool-mms-win-2022-general
+      vmImage: MMS2022
 
     variables:
       # The branch in the azure-sdk/vcpkg repo that is updated daily with the
diff --git a/eng/pipelines/templates/jobs/archetype-sdk-client.yml b/eng/pipelines/templates/jobs/archetype-sdk-client.yml
index 3081c4a55..0f4755c6d 100644
--- a/eng/pipelines/templates/jobs/archetype-sdk-client.yml
+++ b/eng/pipelines/templates/jobs/archetype-sdk-client.yml
@@ -68,8 +68,8 @@ jobs:
       - job:
         displayName: Create API Review for ${{ artifact.name }}
         pool:
-          name: azsdk-pool-mms-win-2019-general
-          vmImage: MMS2019
+          name: azsdk-pool-mms-win-2022-general
+          vmImage: MMS2022
         steps:
           - task: Powershell@2
             inputs:
@@ -110,8 +110,8 @@ jobs:
 
     - job: GenerateReleaseArtifacts
       pool:
-        name: azsdk-pool-mms-win-2019-general
-        vmImage: MMS2019
+        name: azsdk-pool-mms-win-2022-general
+        vmImage: MMS2022
       variables:
         VCPKG_DEFAULT_TRIPLET: 'x64-windows-static'
         Package.EnableSBOMSigning: true
diff --git a/eng/pipelines/templates/jobs/ci.tests.yml b/eng/pipelines/templates/jobs/ci.tests.yml
index bb49b1b3e..ef3fe9463 100644
--- a/eng/pipelines/templates/jobs/ci.tests.yml
+++ b/eng/pipelines/templates/jobs/ci.tests.yml
@@ -259,7 +259,7 @@ jobs:
 
       # Use the job name to create the artifact name for MAP file publishing.
       # Attempts are also noted starting with 1
-      # "Validate Windows2019_UWP_debug_x86" -> "Windows2019_UWP_debug_x86_attempt_1"
+      # "Validate windows2022_UWP_debug_x86" -> "windows2022_UWP_debug_x86_attempt_1"
       - pwsh: |
           $artifactName = "$(Agent.JobName)_attempt_$(System.JobAttempt)"
           $parts = $artifactName -split ' '
diff --git a/eng/pipelines/templates/stages/archetype-cpp-release.yml b/eng/pipelines/templates/stages/archetype-cpp-release.yml
index aaf9eeb9f..5cf118da3 100644
--- a/eng/pipelines/templates/stages/archetype-cpp-release.yml
+++ b/eng/pipelines/templates/stages/archetype-cpp-release.yml
@@ -21,8 +21,8 @@ stages:
             environment: github
 
             pool:
-              name: azsdk-pool-mms-win-2019-general
-              vmImage: MMS2019
+              name: azsdk-pool-mms-win-2022-general
+              vmImage: MMS2022
 
             strategy:
               runOnce:
@@ -62,8 +62,8 @@ stages:
               dependsOn: TagRepository
 
               pool:
-                name: azsdk-pool-mms-win-2019-general
-                vmImage: MMS2019
+                name: azsdk-pool-mms-win-2022-general
+                vmImage: MMS2022
 
               strategy:
                 runOnce:
@@ -92,8 +92,8 @@ stages:
               # This step requires the tag step
               dependsOn: TagRepository
               pool:
-                name: azsdk-pool-mms-win-2019-general
-                vmImage: MMS2019
+                name: azsdk-pool-mms-win-2022-general
+                vmImage: MMS2022
 
               variables:
                 VcpkgPrRepoOwner: Microsoft
@@ -219,8 +219,8 @@ stages:
               environment: github
 
               pool:
-                name: azsdk-pool-mms-win-2019-general
-                vmImage: MMS2019
+                name: azsdk-pool-mms-win-2022-general
+                vmImage: MMS2022
 
               strategy:
                 runOnce:
@@ -247,8 +247,8 @@ stages:
           displayName: Publish to vcpkg daily branch
 
           pool:
-            name: azsdk-pool-mms-win-2019-general
-            vmImage: MMS2019
+            name: azsdk-pool-mms-win-2022-general
+            vmImage: MMS2022
 
           steps:
             - checkout: self
diff --git a/eng/pipelines/templates/stages/platform-matrix-cmakegenerate.json b/eng/pipelines/templates/stages/platform-matrix-cmakegenerate.json
index c6b27adda..073dfd6db 100644
--- a/eng/pipelines/templates/stages/platform-matrix-cmakegenerate.json
+++ b/eng/pipelines/templates/stages/platform-matrix-cmakegenerate.json
@@ -9,8 +9,8 @@
         "VCPKG_DEFAULT_TRIPLET": "x64-linux"
       },
       "Windows": {
-        "Pool": "azsdk-pool-mms-win-2019-general",
-        "OSVmImage": "MMS2019",
+        "Pool": "azsdk-pool-mms-win-2022-general",
+        "OSVmImage": "MMS2022",
         "VCPKG_DEFAULT_TRIPLET": "x64-windows"
       },
       "Mac": {
diff --git a/eng/pipelines/templates/stages/platform-matrix-cmakesourcegenerate.json b/eng/pipelines/templates/stages/platform-matrix-cmakesourcegenerate.json
index 07e9fbc21..f7f1b581e 100644
--- a/eng/pipelines/templates/stages/platform-matrix-cmakesourcegenerate.json
+++ b/eng/pipelines/templates/stages/platform-matrix-cmakesourcegenerate.json
@@ -2,8 +2,8 @@
   "matrix": {
     "OSConfig": {
       "Windows": {
-        "Pool": "azsdk-pool-mms-win-2019-general",
-        "OSVmImage": "MMS2019",
+        "Pool": "azsdk-pool-mms-win-2022-general",
+        "OSVmImage": "MMS2022",
         "CmakeEnvArg": ""
       },
       "Linux": {
diff --git a/eng/pipelines/templates/stages/platform-matrix-live.json b/eng/pipelines/templates/stages/platform-matrix-live.json
index e2e7f2a80..e65f4e6bc 100644
--- a/eng/pipelines/templates/stages/platform-matrix-live.json
+++ b/eng/pipelines/templates/stages/platform-matrix-live.json
@@ -73,6 +73,11 @@
           "Pool": "azsdk-pool-mms-win-2019-general",
           "OSVmImage": "MMS2019",
           "CMAKE_GENERATOR": "Visual Studio 16 2019"
+        },
+        "Win2022": {
+          "Pool": "azsdk-pool-mms-win-2022-general",
+          "OSVmImage": "MMS2022",
+          "CMAKE_GENERATOR": "Visual Studio 17 2022"
         }
       },
       "BuildConfig": {
@@ -191,4 +196,4 @@
       }
     }
   ]
-}
\ No newline at end of file
+}
diff --git a/eng/pipelines/templates/stages/platform-matrix.json b/eng/pipelines/templates/stages/platform-matrix.json
index 8c6315f64..f0d4f0f2d 100644
--- a/eng/pipelines/templates/stages/platform-matrix.json
+++ b/eng/pipelines/templates/stages/platform-matrix.json
@@ -29,11 +29,29 @@
       }
     },
     {
-      "StaticConfigs": {
-        "Win2019": {
+      "StaticConfigs": { 
+        "Win2019_x64_Release": {
           "OSVmImage": "MMS2019",
           "Pool": "azsdk-pool-mms-win-2019-general",
-          "CMAKE_GENERATOR": "Visual Studio 16 2019"
+          "CMAKE_GENERATOR": "Visual Studio 16 2019",
+          "CMAKE_GENERATOR_PLATFORM": "x64",
+          "VCPKG_DEFAULT_TRIPLET": "x64-windows-static",
+          "BuildArgs": "--parallel 8 --config Release"
+        }
+      }, 
+      "BuildSettings": {
+        "Curl": {
+          "CmakeArgs": " -DBUILD_TRANSPORT_CURL=ON"
+        },
+        "WinHttp": { }
+      }
+    },
+    {
+      "StaticConfigs": {
+        "Win2022": {
+          "OSVmImage": "MMS2022",
+          "Pool": "azsdk-pool-mms-win-2022-general",
+          "CMAKE_GENERATOR": "Visual Studio 17 2022"
         }
       },
       "TargetPlatform": {
@@ -61,7 +79,7 @@
       "StaticConfigs": {
         "Win2022": {
           "OSVmImage": "windows-2022",
-          "Pool": "Azure Pipelines",
+          "Pool": "azsdk-pool-mms-win-2022-general",
           "RunProxyTests": true,
           "CMAKE_GENERATOR": "Visual Studio 17 2022"
         }
@@ -86,11 +104,11 @@
     },
     {
       "StaticConfigs": {
-        "Win2019": {
+        "Win2022": {
           "VcpkgInstall": "openssl",
-          "OSVmImage": "MMS2019",
-          "Pool": "azsdk-pool-mms-win-2019-general",
-          "CMAKE_GENERATOR": "Visual Studio 16 2019",
+          "OSVmImage": "MMS2022",
+          "Pool": "azsdk-pool-mms-win-2022-general",
+          "CMAKE_GENERATOR": "Visual Studio 17 2022",
           "PublishMapFiles": "true"
         }
       },
diff --git a/eng/scripts/Get-BinarySizes.ps1 b/eng/scripts/Get-BinarySizes.ps1
index 563574074..bebb6c474 100644
--- a/eng/scripts/Get-BinarySizes.ps1
+++ b/eng/scripts/Get-BinarySizes.ps1
@@ -48,10 +48,11 @@ function getTargetOs {
         return $OsVMImage
     }
 
-    if ($OsVMImage -eq "MMS2019") {
+    if ($OsVMImage -match "^MMS2019$|^win-2019$") {
         return "win-2019"
     }
-    if ($OsVMImage -eq "windows-2022") {
+
+    if ($OsVMImage -match "^MMS2022$|^win-2022$") {
         return "win-2022"
     }
 
@@ -88,11 +89,11 @@ function getToolChain {
         return "AppleClang 12"
     }
 
-    if ($OSVmImage -eq "MMS2019") {
+    if ($OSVmImage -match "MMS\d{4}") {
         return "MSVC"
     }
 
-	if ($OSVmImage -eq "windows-2022") {
+	if ($OSVmImage -match "windows-\d{4}") {
         return "MSVC17"
     }
 
@@ -116,7 +117,7 @@ function getTargetPlatform {
         return "macos"
     }
 
-    if ($OSVmImage -eq 'MMS2019' -or $OsVMImage -eq "windows-2022") {
+    if ($OSVmImage -match 'MMS\d{4}' -or $OsVMImage -match "windows-\d{4}") {
         if (!$env:CMAKE_SYSTEM_NAME -and !$CmakeArgs.Contains('WindowsStore')) {
             return 'win32'
         } elseif ($env:CMAKE_SYSTEM_NAME -eq 'WindowsStore' -or $CmakeArgs.Contains('WindowsStore')) {