diff --git a/.github/workflows/bundle-audit.yml b/.github/workflows/bundle-audit.yml
index 400da2af6..aeeb6feb4 100644
--- a/.github/workflows/bundle-audit.yml
+++ b/.github/workflows/bundle-audit.yml
@@ -15,7 +15,7 @@ jobs:
     timeout-minutes: 90
     strategy:
       fail-fast: false
-    runs-on: windows-2019
+    runs-on: windows-2022
     steps:
       - name: Set up Ruby
         uses: ruby/setup-ruby@v1
diff --git a/.github/workflows/windows.yml b/.github/workflows/windows.yml
index 6653c0627..8b76ad7a0 100644
--- a/.github/workflows/windows.yml
+++ b/.github/workflows/windows.yml
@@ -14,7 +14,7 @@ jobs:
     timeout-minutes: 90
     strategy:
       fail-fast: false
-    runs-on: windows-2019
+    runs-on: windows-2022
     steps:
       - name: Set up Ruby
         uses: ruby/setup-ruby@v1
@@ -41,7 +41,7 @@ jobs:
   check_package_size:
     name: Check Package Size
     needs: build
-    runs-on: windows-2019
+    runs-on: windows-2022
     steps:
       - uses: actions/checkout@v4
       - uses: actions/download-artifact@v4
@@ -55,7 +55,7 @@ jobs:
   installation_test:
     name: Installation Test
     needs: build
-    runs-on: windows-2019
+    runs-on: windows-2022
     steps:
       - uses: actions/checkout@v4
       - uses: actions/download-artifact@v4
@@ -75,7 +75,7 @@ jobs:
   update_from_v4_test:
     name: Migration From v4 Test
     needs: build
-    runs-on: windows-2019
+    runs-on: windows-2022
     steps:
       - uses: actions/checkout@v4
       - uses: actions/download-artifact@v4
@@ -94,7 +94,7 @@ jobs:
   update_from_v5_test:
     name: Update From v5 Test
     needs: build
-    runs-on: windows-2019
+    runs-on: windows-2022
     steps:
       - uses: actions/checkout@v4
       - uses: actions/download-artifact@v4
@@ -113,7 +113,7 @@ jobs:
   serverspec_test:
     name: Serverspec Test
     needs: build
-    runs-on: windows-2019
+    runs-on: windows-2022
     steps:
       - uses: actions/checkout@v4
       - uses: actions/download-artifact@v4
diff --git a/fluent-package/msi/Dockerfile b/fluent-package/msi/Dockerfile
index 0bd687a4f..f140c34e0 100644
--- a/fluent-package/msi/Dockerfile
+++ b/fluent-package/msi/Dockerfile
@@ -16,7 +16,7 @@
 
 # The latest chocolatey requires .net 4.8, and wixtoolset requires .net 3.5,
 # To satisfy both of them without reboot, use sdk image.
-ARG FROM=mcr.microsoft.com/dotnet/framework/sdk:3.5-windowsservercore-ltsc2019
+ARG FROM=mcr.microsoft.com/dotnet/framework/sdk:3.5-windowsservercore-ltsc2022
 FROM ${FROM}
 
 # Launch the following command as if cmd /S /C ...