diff --git a/images/windows/Windows2019-Readme.md b/images/windows/Windows2019-Readme.md
index c59ad5984..ca189832b 100644
--- a/images/windows/Windows2019-Readme.md
+++ b/images/windows/Windows2019-Readme.md
@@ -1,15 +1,13 @@
 | Announcements |
 |-|
+| [[Windows ,Ubuntu, MacOs ] Breaking change: Updating  Azure PowerShell Module version as 12.5.x   from  2025-07-04](https://github.com/actions/runner-images/issues/12333) |
 | [[Windows & Ubuntu] .NET 6 will be removed from the images on  2025-08-01.](https://github.com/actions/runner-images/issues/12241) |
-| [[Ubuntu 22.04 and Windows 2022] Default Nodejs version will be set to 20 on 2025-06-02](https://github.com/actions/runner-images/issues/12143) |
 | [The Windows 2019 Actions runner image will begin deprecation on 2025-06-01 and will be fully unsupported by 2025-06-30](https://github.com/actions/runner-images/issues/12045) |
-| [[Windows, Ubuntu] Python 3.8.x will be removed from 2025-06-06](https://github.com/actions/runner-images/issues/12034) |
-| [[Windows 19 and 22] Ruby version 3.0 will be removed from Windows images on 2025-06-06 and 3.3 will be set as default.](https://github.com/actions/runner-images/issues/12033) |
 | [Windows Server 2025 is now available](https://github.com/actions/runner-images/issues/11228) |
 ***
 # Windows Server 2019
 - OS Version: 10.0.17763 Build 7322
-- Image Version: 20250602.2.0
+- Image Version: 20250609.1.0
 
 ## Windows features
 - Windows Subsystem for Linux (WSLv1): Enabled
@@ -18,13 +16,13 @@
 
 ### Language and Runtime
 - Bash 5.2.37(1)-release
-- Go 1.24.3
+- Go 1.24.4
 - Julia 1.11.5
 - Kotlin 2.1.10
 - LLVM 18.1.8
 - Node 18.20.8
 - Perl 5.32.1
-- PHP 8.4.7
+- PHP 8.4.8
 - Python 3.9.13
 - Ruby 3.3.8
 
@@ -38,7 +36,7 @@
 - pip 25.1.1 (python 3.9)
 - Pipx 1.7.1
 - RubyGems 3.5.22
-- Vcpkg (build from commit 181f538ff1)
+- Vcpkg (build from commit 984f9232b2)
 - Yarn 1.22.22
 
 #### Environment variables
@@ -50,8 +48,8 @@
 ### Project Management
 - Ant 1.10.15
 - Gradle 8.14
-- Maven 3.9.9
-- sbt 1.11.0
+- Maven 3.9.10
+- sbt 1.11.2
 
 ### Tools
 - 7zip 24.09
@@ -62,14 +60,14 @@
 - Bicep 0.36.1
 - Cabal 3.14.2.0
 - CMake 3.31.6
-- CodeQL Action Bundle 2.21.3
+- CodeQL Action Bundle 2.21.4
 - Docker 27.5.1
 - Docker Compose v2 2.32.2
 - Docker-wincred 0.9.3
 - ghc 9.12.2
 - Git 2.49.0.windows.1
 - Git LFS 3.6.1
-- Google Cloud CLI 524.0.0
+- Google Cloud CLI 525.0.0
 - ImageMagick 7.1.1-47
 - InnoSetup 6.4.0
 - jq 1.7.1
@@ -84,7 +82,7 @@
 - OpenSSL 1.1.1w
 - Packer 1.12.0
 - Parcel 2.15.2
-- Pulumi 3.173.0
+- Pulumi 3.175.0
 - R 4.4.2
 - Service Fabric SDK 10.1.2493.9590
 - Stack 3.5.1
@@ -98,11 +96,11 @@
 - Ninja 1.12.1
 
 ### CLI Tools
-- Alibaba Cloud CLI 3.0.280
-- AWS CLI 2.27.26
-- AWS SAM CLI 1.139.0
+- Alibaba Cloud CLI 3.0.282
+- AWS CLI 2.27.31
+- AWS SAM CLI 1.140.0
 - AWS Session Manager CLI 1.2.707.0
-- Azure CLI 2.73.0
+- Azure CLI 2.74.0
 - Azure DevOps CLI extension 1.0.1
 - Cloud Foundry CLI 8.14.0
 - GitHub CLI 2.74.0
@@ -114,7 +112,7 @@
 - Rustup 1.28.2
 
 #### Packages
-- bindgen 0.71.1
+- bindgen 0.72.0
 - cargo-audit 0.21.2
 - cargo-outdated 0.17.0
 - cbindgen 0.29.0
@@ -124,8 +122,8 @@
 ### Browsers and Drivers
 - Google Chrome 137.0.7151.69
 - Chrome Driver 137.0.7151.68
-- Microsoft Edge 137.0.3296.52
-- Microsoft Edge Driver 137.0.3296.52
+- Microsoft Edge 137.0.3296.68
+- Microsoft Edge Driver 137.0.3296.68
 - Mozilla Firefox 139.0.1
 - Gecko Driver 0.36.0
 - IE Driver 4.14.0.0
@@ -171,8 +169,8 @@ Note: MSYS2 is pre-installed on image but not added to PATH.
 
 #### Go
 - 1.22.12
-- 1.23.9
-- 1.24.3
+- 1.23.10
+- 1.24.4
 
 #### Node.js
 - 18.20.8
@@ -180,12 +178,11 @@ Note: MSYS2 is pre-installed on image but not added to PATH.
 - 22.16.0
 
 #### Python
-- 3.8.10
 - 3.9.13
 - 3.10.11
 - 3.11.9
 - 3.12.10
-- 3.13.3
+- 3.13.4
 
 #### PyPy
 - 2.7.18 [PyPy 7.3.19]
@@ -508,7 +505,7 @@ Note: MSYS2 is pre-installed on image but not added to PATH.
 
 #### Powershell Modules
 - Az: 12.1.0
-- AWSPowershell: 4.1.832
+- AWSPowershell: 4.1.836
 - DockerMsftProvider: 1.0.0.8
 - MarkdownPS: 1.10
 - Microsoft.Graph: 2.28.0