diff --git a/images/win/Windows2019-Readme.md b/images/win/Windows2019-Readme.md
index 59a0f8066..c550a650b 100644
--- a/images/win/Windows2019-Readme.md
+++ b/images/win/Windows2019-Readme.md
@@ -1,6 +1,6 @@
 # Microsoft Windows Server 2019 Datacenter
 - OS Version: 10.0.17763 Build 1935
-- Image Version: 20210525.0
+- Image Version: 20210531.1
 
 ## Enabled windows optional features
 - Windows Subsystem for Linux [WSLv1]
@@ -19,14 +19,14 @@
 ### Package Management
 - Chocolatey 0.10.15
 - Composer 2.0.14
-- Helm 3.5.4
+- Helm 3.6.0
 - Miniconda 4.9.2
 - NPM 6.14.13
 - NuGet 5.9.1.11
 - pip 21.1.2 (python 3.7)
-- Pipx 0.16.2.1
+- Pipx 0.16.3
 - RubyGems 2.7.6.3
-- Vcpkg  (build from master \<83f9a6c>)
+- Vcpkg  (build from master \<7bc5b8c>)
 - Yarn 1.22.10
 
 #### Environment variables
@@ -47,9 +47,9 @@
 - Bazel 4.1.0
 - Bazelisk 1.9.0
 - Cabal 3.4.0.0
-- CMake 3.20.2
+- CMake 3.20.3
 - CodeQL Action Bundle 2.5.5
-- Docker 20.10.4
+- Docker 20.10.5
 - Docker-compose 1.29.1
 - ghc 9.0.1
 - Git 2.31.1
@@ -57,7 +57,7 @@
 - Google Cloud SDK 342.0.0
 - InnoSetup 6.1.2
 - jq 1.6
-- Kind 0.11.0
+- Kind 0.11.1
 - Kubectl 1.21.1
 - Mercurial 5.0
 - Mingw-w64 8.1.0
@@ -75,8 +75,8 @@
 - zstd 1.5.0
 
 ### CLI Tools
-- Alibaba Cloud CLI 3.0.75
-- AWS CLI 2.2.5
+- Alibaba Cloud CLI 3.0.77
+- AWS CLI 2.2.7
 - AWS SAM CLI 1.23.0
 - AWS Session Manager CLI 1.2.54.0
 - Azure CLI 2.24.0
@@ -102,8 +102,8 @@
 ### Browsers and webdrivers
 - Google Chrome 91.0.4472.77
 - Chrome Driver 91.0.4472.19
-- Microsoft Edge 90.0.818.66
-- Microsoft Edge Driver 90.0.818.66
+- Microsoft Edge 91.0.864.37
+- Microsoft Edge Driver 91.0.864.37
 - Mozilla Firefox 88.0.1
 - Gecko Driver 0.29.1
 - IE Driver 3.150.1.0
@@ -218,7 +218,7 @@ Note: MSYS2 is pre-installed on image but not added to PATH.
 ### Web Servers
 | Name   | Version | ConfigFile                            | ServiceName | ServiceStatus | ListenPort |
 | ------ | ------- | ------------------------------------- | ----------- | ------------- | ---------- |
-| Apache | 2.4.47  | C:\tools\Apache24\conf\httpd.conf     | Apache      | Stopped       | 80         |
+| Apache | 2.4.48  | C:\tools\Apache24\conf\httpd.conf     | Apache      | Stopped       | 80         |
 | Nginx  | 1.21.0  | C:\tools\nginx-1.21.0\conf\nginx.conf | nginx       | Stopped       | 80         |
 
 ### Visual Studio Enterprise 2019
@@ -517,7 +517,7 @@ All other versions are saved but not installed.
 | ------------------ | ---------------- |
 | DockerMsftProvider | 1.0.0.8          |
 | MarkdownPS         | 1.9              |
-| Pester             | 3.4.0<br>5.2.1   |
+| Pester             | 3.4.0<br>5.2.2   |
 | PowerShellGet      | 1.0.0.1<br>2.2.5 |
 | PSScriptAnalyzer   | 1.19.1           |
 | PSWindowsUpdate    | 2.2.0.2          |
@@ -555,7 +555,7 @@ All other versions are saved but not installed.
 | ------------------------------------------------------------------------- | ------------------------------------------------------------------------ | ---------- |
 | mcr.microsoft.com/dotnet/framework/aspnet:4.8-windowsservercore-ltsc2019  | sha256:6c8ea03414851b5a77a951a9fc82a43e580e816b12e9d05d6a5918a76c2dd7c1  | 2021-05-11 |
 | mcr.microsoft.com/dotnet/framework/runtime:4.8-windowsservercore-ltsc2019 | sha256:c615be2cb06c4f4386f4ba424239f2172af7a3c8360ab0008131828d50fe020f  | 2021-05-11 |
-| mcr.microsoft.com/dotnet/framework/sdk:4.8-windowsservercore-ltsc2019     | sha256:9ae2cdbf93d7a50bc195ea72415afed2636b60b1d4a7028c1a9f68ada07fafec  | 2021-05-11 |
+| mcr.microsoft.com/dotnet/framework/sdk:4.8-windowsservercore-ltsc2019     | sha256:a3b51566290b6aa485de6d8ac3d8cbf008f560feda73ed1addb208166cbdd3ad  | 2021-05-25 |
 | mcr.microsoft.com/windows/nanoserver:1809                                 | sha256:7810b00b2b0ce434cf8a420627b3aba335a40e1b805e1be2e02241b7446f7a00  | 2021-05-07 |
 | mcr.microsoft.com/windows/servercore:ltsc2019                             | sha256:edd6d6de1e7252d2d434af58798db1d96762d738f60e15b24ed631f55e26681d  | 2021-05-08 |