diff --git a/images/linux/Ubuntu1604-README.md b/images/linux/Ubuntu1604-README.md
index c06b5d7b..57198a44 100644
--- a/images/linux/Ubuntu1604-README.md
+++ b/images/linux/Ubuntu1604-README.md
@@ -1,11 +1,13 @@
 | Announcements |
 |-|
+| [Default Node.JS will be switched to 14.x on all platforms ](https://github.com/actions/virtual-environments/issues/1953) |
+| [[macOS] Default Python will be upgraded to 3.9](https://github.com/actions/virtual-environments/issues/1929) |
 | [.NET 5.0 will become a default .NET version on November, 10](https://github.com/actions/virtual-environments/issues/1891) |
 | [[Ubuntu] [Windows] Boost 1.69.0 will be deprecated on November, 10](https://github.com/actions/virtual-environments/issues/1847) |
 | [Ubuntu-latest workflows will use Ubuntu-20.04](https://github.com/actions/virtual-environments/issues/1816) |
 ***
 # Ubuntu 16.04.7 LTS
-- Image Version: 20201026.1
+- Image Version: 20201102.0
 
 ## Installed Software
 ### Language and Runtime
@@ -14,7 +16,7 @@
 - Clang 6.0.0, 8.0.0, 9.0.1
 - Erlang 11.1
 - Mono 6.12.0.90
-- Node 12.19.0
+- Node 14.15.0
 - Python 2.7.12
 - Python3 3.5.2
 - PowerShell 7.0.3
@@ -24,8 +26,8 @@
 
 ### Package Management
 - Gem 3.1.4
-- Helm 3.3.4
-- Homebrew 2.5.6
+- Helm 3.4.0
+- Homebrew 2.5.8
 - Miniconda 4.8.3
 - Npm 6.14.8
 - Pip 8.1.1
@@ -48,7 +50,7 @@
 - Bazel 3.7.0
 - Bazelisk 1.7.3
 - CMake 3.17.0
-- CodeQL Action Bundle 2.3.0
+- CodeQL Action Bundle 2.3.1+202010222007
 - curl 7.47.0
 - Docker Compose 1.27.4
 - Docker-Buildx 0.4.2
@@ -56,21 +58,21 @@
 - Git 2.29.0
 - Git LFS 2.12.0
 - Git-ftp 1.0.2
-- Google Cloud SDK 315.0.0
+- Google Cloud SDK 316.0.0
 - Haveged 1.9.1
-- Heroku 7.46.2
+- Heroku 7.47.0
 - HHVM (HipHop VM) 4.56.1
 - jq 1.5
 - Kind 0.9.0
 - Kubectl 1.19.3
-- Kustomize 3.8.5
+- Kustomize 3.8.6
 - Leiningen 2.9.4
 - m4 1.4.17
 - Mercurial 4.4.1
-- Minikube 1.14.1
-- Newman 5.2.0
+- Minikube 1.14.2
+- Newman 5.2.1
 - nvm 0.36.0
-- Packer 1.6.4
+- Packer 1.6.5
 - PhantomJS 2.1.1
 - Pulumi 2.12.1
 - R 4.0.3
@@ -86,14 +88,14 @@
 
 ### CLI Tools
 - Alibaba Cloud CLI 3.0.60
-- AWS CLI 1.18.164
+- AWS CLI 1.18.169
 - AWS CLI Session manager plugin 1.2.7.0
-- AWS SAM CLI 1.6.2
-- Azure CLI (azure-cli) 2.13.0
+- AWS SAM CLI 1.7.0
+- Azure CLI (azure-cli) 2.14.0
 - Azure CLI (azure-devops) 0.18.0
-- GitHub CLI 1.1.0
+- GitHub CLI 1.2.0
 - Hub CLI 2.14.2
-- Netlify CLI 2.65.7
+- Netlify CLI 2.67.2
 - oc CLI 4.5.0
 - ORAS CLI 0.8.1
 - Vercel CLI 20.1.2
@@ -109,8 +111,8 @@
 ### PHP
 | Tool     | Version                                   |
 | -------- | ----------------------------------------- |
-| PHP      | 5.6.40 7.0.33 7.1.33 7.2.34 7.3.23 7.4.11 |
-| Composer | 2.0.2                                     |
+| PHP      | 5.6.40 7.0.33 7.1.33 7.2.34 7.3.24 7.4.12 |
+| Composer | 2.0.4                                     |
 | PHPUnit  | 7.5.20                                    |
 
 ### Haskell
@@ -126,16 +128,16 @@
 
 #### Packages
 - Bindgen 0.55.1
-- Cargo audit 0.12.1
-- Cargo outdated 0.9.11
+- Cargo audit 0.13.1
+- Cargo outdated 0.9.13
 - Cargo clippy 0.0.212
 - Cbindgen 0.15.0
 - Rustfmt 1.4.20
 
 ### Browsers and Drivers
-- Google Chrome 86.0.4240.111
+- Google Chrome 86.0.4240.183
 - ChromeDriver 86.0.4240.22
-- Mozilla Firefox 81.0.2
+- Mozilla Firefox 82.0
 - Geckodriver 0.27.0
 
 ### .NET Core SDK
@@ -150,7 +152,7 @@
 - sqlite3 3.11.0
 
 #### MySQL
-- MySQL 5.7.31
+- MySQL 5.7.32
 - MySQL Server (user:root password:root)
 - MS SQL Server Client Tools
 
@@ -178,9 +180,9 @@
 
 #### Node.js
 - 8.17.0
-- 10.22.1
+- 10.23.0
 - 12.19.0
-- 14.14.0
+- 14.15.0
 
 #### Go
 - 1.11.13
diff --git a/images/linux/scripts/SoftwareReport/SoftwareReport.Common.psm1 b/images/linux/scripts/SoftwareReport/SoftwareReport.Common.psm1
index 1989caf4..15a19653 100644
--- a/images/linux/scripts/SoftwareReport/SoftwareReport.Common.psm1
+++ b/images/linux/scripts/SoftwareReport/SoftwareReport.Common.psm1
@@ -240,6 +240,17 @@ function Get-CachedDockerImages {
     return $images
 }
 
+function Get-CachedDockerImagesTableData {
+    return (sudo docker images --digests --format "*{{.Repository}}:{{.Tag}}|{{.Digest}} |{{.CreatedAt}}").Split("*")     | Where-Object { $_ } |  ForEach-Object {
+      $parts=$_.Split("|")
+      [PSCustomObject] @{
+             "Repository:Tag" = $parts[0]
+              "Digest" = $parts[1]
+              "Created" = $parts[2].split(' ')[0]
+         }
+    }
+}
+
 function Get-AptPackages {
     $toolsetJson = Get-ToolsetContent
     $apt = $toolsetJson.apt
@@ -252,4 +263,4 @@ function Get-PipxVersion {
     $result -match "(?<version>\d+\.\d+\.\d+\.?\d*)" | Out-Null
     $pipxVersion = $Matches.Version
     return "Pipx $pipxVersion"
-}
\ No newline at end of file
+}
diff --git a/images/linux/scripts/SoftwareReport/SoftwareReport.Generator.ps1 b/images/linux/scripts/SoftwareReport/SoftwareReport.Generator.ps1
index df77ea23..9cf57034 100644
--- a/images/linux/scripts/SoftwareReport/SoftwareReport.Generator.ps1
+++ b/images/linux/scripts/SoftwareReport/SoftwareReport.Generator.ps1
@@ -224,7 +224,8 @@ $markdown += Build-AndroidTable | New-MDTable
 $markdown += New-MDNewLine
 
 $markdown += New-MDHeader "Cached Docker images" -Level 3
-$markdown += New-MDList -Style Unordered -Lines @(Get-CachedDockerImages)
+$markdown += Get-CachedDockerImagesTableData | New-MDTable
+$markdown += New-MDNewLine
 
 $markdown += New-MDHeader "Installed apt packages" -Level 3
 $markdown += New-MDList -Style Unordered -Lines @(Get-AptPackages)
diff --git a/images/linux/scripts/base/apt.sh b/images/linux/scripts/base/apt.sh
index 1efbb672..cf221452 100644
--- a/images/linux/scripts/base/apt.sh
+++ b/images/linux/scripts/base/apt.sh
@@ -1,9 +1,5 @@
 #!/bin/bash -e
 
-export DEBIAN_FRONTEND=noninteractive
-apt-get -yq update
-apt-get -yq dist-upgrade
-
 # Stop and disable apt-daily upgrade services;
 systemctl stop apt-daily.timer
 systemctl disable apt-daily.timer
@@ -16,7 +12,7 @@ systemctl disable apt-daily-upgrade.service
 sudo sed -i 's/APT::Periodic::Update-Package-Lists "1"/APT::Periodic::Update-Package-Lists "0"/' /etc/apt/apt.conf.d/20auto-upgrades
 
 # Enable retry logic for apt up to 10 times
-echo "APT::Acquire::Retries \"10\";" > /etc/apt/apt.conf.d/80-retries 
+echo "APT::Acquire::Retries \"10\";" > /etc/apt/apt.conf.d/80-retries
 
 # Configure apt to always assume Y
 echo "APT::Get::Assume-Yes \"true\";" > /etc/apt/apt.conf.d/90assumeyes
diff --git a/images/linux/scripts/base/repos.sh b/images/linux/scripts/base/repos.sh
index 9005d32a..a489c62a 100644
--- a/images/linux/scripts/base/repos.sh
+++ b/images/linux/scripts/base/repos.sh
@@ -16,4 +16,7 @@ curl -L https://packages.microsoft.com/keys/microsoft.asc | apt-key add -
 
 curl https://packages.microsoft.com/keys/microsoft.asc | gpg --dearmor > microsoft.gpg
 mv microsoft.gpg /etc/apt/trusted.gpg.d/microsoft.gpg
-apt-get update
\ No newline at end of file
+
+# update
+apt-get -yq update
+apt-get -yq dist-upgrade
diff --git a/images/linux/scripts/installers/azpowershell.sh b/images/linux/scripts/installers/azpowershell.sh
index 13253b5f..f18492c5 100644
--- a/images/linux/scripts/installers/azpowershell.sh
+++ b/images/linux/scripts/installers/azpowershell.sh
@@ -18,6 +18,10 @@ pwsh -Command "Update-Module -Name PowerShellGet -Force"
 # Install Azure CLI (instructions taken from https://docs.microsoft.com/en-us/cli/azure/install-azure-cli)
 for version in ${versions[@]}; do
     pwsh -Command "Save-Module -Name Az -LiteralPath /usr/share/az_$version -RequiredVersion $version -Force -Verbose"
+    if isUbuntu20; then
+        rm -rf "/usr/share/az_$version/Az.Accounts"
+        pwsh -Command "Save-Module -Name Az.Accounts -LiteralPath /usr/share/az_$version -RequiredVersion 1.9.5 -Force -Verbose"
+    fi
 done
 
 # Run tests to determine that the software installed as expected
diff --git a/images/linux/scripts/installers/powershellcore.sh b/images/linux/scripts/installers/powershellcore.sh
index 4f700fbc..0ac52072 100644
--- a/images/linux/scripts/installers/powershellcore.sh
+++ b/images/linux/scripts/installers/powershellcore.sh
@@ -9,8 +9,7 @@ source $HELPER_SCRIPTS/os.sh
 
 # Install Powershell
 if isUbuntu20 ; then
-    dotnet tool install --tool-path /opt/microsoft/powershell/7 powershell
-    ln -s /opt/microsoft/powershell/7/pwsh /usr/bin/pwsh
+    snap install powershell --classic --channel=edge/useedge
 fi
 
 if isUbuntu16 || isUbuntu18 ; then
diff --git a/images/linux/toolsets/toolset-1604.json b/images/linux/toolsets/toolset-1604.json
index 1136ae92..1c5ff532 100644
--- a/images/linux/toolsets/toolset-1604.json
+++ b/images/linux/toolsets/toolset-1604.json
@@ -42,8 +42,6 @@
             "arch": "x64",
             "platform" : "linux",
             "versions": [
-                "1.11.*",
-                "1.12.*",
                 "1.13.*",
                 "1.14.*",
                 "1.15.*"
@@ -57,7 +55,6 @@
             "platform_version": "16.04",
             "arch": "x64",
             "versions": [
-                "1.69.0",
                 "1.72.0"
             ]
         }
diff --git a/images/linux/toolsets/toolset-1804.json b/images/linux/toolsets/toolset-1804.json
index de611ebc..226dd190 100644
--- a/images/linux/toolsets/toolset-1804.json
+++ b/images/linux/toolsets/toolset-1804.json
@@ -42,8 +42,6 @@
             "arch": "x64",
             "platform" : "linux",
             "versions": [
-                "1.11.*",
-                "1.12.*",
                 "1.13.*",
                 "1.14.*",
                 "1.15.*"
@@ -57,7 +55,6 @@
             "platform_version": "18.04",
             "arch": "x64",
             "versions": [
-                "1.69.0",
                 "1.72.0"
             ]
         }
diff --git a/images/linux/ubuntu1604.json b/images/linux/ubuntu1604.json
index a519b30d..6168f4bf 100644
--- a/images/linux/ubuntu1604.json
+++ b/images/linux/ubuntu1604.json
@@ -72,6 +72,9 @@
         {
             "type": "shell",
             "script": "{{template_dir}}/scripts/base/apt.sh",
+            "environment_vars": [
+                "DEBIAN_FRONTEND=noninteractive"
+            ],
             "execute_command": "sudo sh -c '{{ .Vars }} {{ .Path }}'"
         },
         {
diff --git a/images/linux/ubuntu1804.json b/images/linux/ubuntu1804.json
index 977464e3..6fc3f813 100644
--- a/images/linux/ubuntu1804.json
+++ b/images/linux/ubuntu1804.json
@@ -75,6 +75,9 @@
         {
             "type": "shell",
             "script": "{{template_dir}}/scripts/base/apt.sh",
+            "environment_vars": [
+                "DEBIAN_FRONTEND=noninteractive"
+            ],
             "execute_command": "sudo sh -c '{{ .Vars }} {{ .Path }}'"
         },
         {
diff --git a/images/linux/ubuntu2004.json b/images/linux/ubuntu2004.json
index 54bc6fb5..bde4024c 100644
--- a/images/linux/ubuntu2004.json
+++ b/images/linux/ubuntu2004.json
@@ -74,9 +74,20 @@
             ],
             "execute_command": "sudo sh -c '{{ .Vars }} {{ .Path }}'"
         },
+        {
+            "type": "shell",
+            "expect_disconnect": true,
+            "scripts": [
+                "{{template_dir}}/scripts/base/reboot.sh"
+            ],
+            "execute_command": "/bin/sh -c '{{ .Vars }} {{ .Path }}'"
+        },
         {
             "type": "shell",
             "script": "{{template_dir}}/scripts/base/apt.sh",
+            "environment_vars": [
+                "DEBIAN_FRONTEND=noninteractive"
+            ],
             "execute_command": "sudo sh -c '{{ .Vars }} {{ .Path }}'"
         },
         {
diff --git a/images/macos/provision/core/node.sh b/images/macos/provision/core/node.sh
index 59e727ce..194437a9 100644
--- a/images/macos/provision/core/node.sh
+++ b/images/macos/provision/core/node.sh
@@ -27,8 +27,8 @@ if is_Less_Catalina; then
   npm install -g appcenter-cli@^1.0.0
 else
   # Install Node.JS 12 for macOS >= 10.15
-  brew install node@12
-  brew link node@12 --force
+  brew install node@14
+  brew link node@14 --force
 
   for module in ${node_modules[@]}; do
     echo "Install $module"
diff --git a/images/macos/provision/core/rust.sh b/images/macos/provision/core/rust.sh
index de82c7b4..89e70537 100644
--- a/images/macos/provision/core/rust.sh
+++ b/images/macos/provision/core/rust.sh
@@ -11,7 +11,8 @@ CARGO_HOME=$HOME/.cargo
 source $CARGO_HOME/env
 
 echo Install common tools...
+rustup component add rustfmt clippy
 cargo install bindgen cbindgen cargo-audit cargo-outdated
 
 echo Cleanup Cargo registry cached data...
-rm -rf $CARGO_HOME/registry/*
\ No newline at end of file
+rm -rf $CARGO_HOME/registry/*
diff --git a/images/macos/provision/core/xcode-tools.sh b/images/macos/provision/core/xcode-tools.sh
index 773b07a9..5c491708 100755
--- a/images/macos/provision/core/xcode-tools.sh
+++ b/images/macos/provision/core/xcode-tools.sh
@@ -77,6 +77,7 @@ runFirstLaunch $DEFAULT_XCODE_VERSION
 if is_Catalina; then
     ln -sf /Applications/Xcode_11.2.1.app /Applications/Xcode_11.2.app
     ln -sf /Applications/Xcode_11.3.1.app /Applications/Xcode_11.3.app
+    ln -sf /Applications/Xcode_11.4.1.app /Applications/Xcode_11.4.app
 fi
 
 echo "Setting Xcode ${DEFAULT_XCODE_VERSION} as default"
diff --git a/images/macos/tests/Node.Tests.ps1 b/images/macos/tests/Node.Tests.ps1
index 7fde021d..65005eb6 100644
--- a/images/macos/tests/Node.Tests.ps1
+++ b/images/macos/tests/Node.Tests.ps1
@@ -4,7 +4,7 @@ Import-Module "$PSScriptRoot/../helpers/Tests.Helpers.psm1"
 Describe "Node.JS" {
     BeforeAll {
         $os = Get-OSVersion
-        $expectedNodeVersion = if ($os.IsHigherThanMojave) { "v12.*" } else { "v8.*" }
+        $expectedNodeVersion = if ($os.IsHigherThanMojave) { "v14.*" } else { "v8.*" }
     }
 
     It "Node.JS is installed" {
@@ -29,7 +29,7 @@ Describe "NVM" {
         $nvmPath = Join-Path $env:HOME ".nvm" "nvm.sh"
         $nvmInitCommand = ". $nvmPath > /dev/null 2>&1 || true"
     }
-    
+
     It "Nvm is installed" {
         $nvmPath | Should -Exist
         "$nvmInitCommand && nvm --version" | Should -ReturnZeroExitCode
@@ -43,7 +43,7 @@ Describe "NVM" {
             param (
                 [string] $NvmVersion
             )
-            
+
             "$nvmInitCommand && nvm ls $($NvmVersion)" | Should -ReturnZeroExitCode
         }
     }
diff --git a/images/macos/toolsets/toolset-10.15.json b/images/macos/toolsets/toolset-10.15.json
index 11a7e016..79f6d9eb 100644
--- a/images/macos/toolsets/toolset-10.15.json
+++ b/images/macos/toolsets/toolset-10.15.json
@@ -2,7 +2,7 @@
     "xcode": {
         "default": "12",
         "versions": [
-            "12.2_beta", "12.1", "12", "11.7", "11.6", "11.5", "11.4.1", "11.4", "11.3.1", "11.2.1", "11.1", "11", "10.3"
+            "12.2_beta", "12.1", "12", "11.7", "11.6", "11.5", "11.4.1", "11.3.1", "11.2.1", "10.3"
         ]
     },
     "xamarin": {
@@ -168,8 +168,6 @@
             "arch": "x64",
             "platform" : "darwin",
             "versions": [
-                "1.11.*",
-                "1.12.*",
                 "1.13.*",
                 "1.14.*",
                 "1.15.*"
diff --git a/images/win/scripts/Installers/Configure-Shell.ps1 b/images/win/scripts/Installers/Configure-Shell.ps1
deleted file mode 100644
index 61b30bf3..00000000
--- a/images/win/scripts/Installers/Configure-Shell.ps1
+++ /dev/null
@@ -1,23 +0,0 @@
-# Create shells folder
-$shellPath = "C:\shells"
-New-Item -Path $shellPath -ItemType Directory | Out-Null
-
-# sh and bash <--> C:\msys64\usr\bin\bash.exe
-New-Item -ItemType SymbolicLink -Path "$shellPath\bash.exe" -Target "C:\msys64\bin\bash.exe" | Out-Null
-New-Item -ItemType SymbolicLink -Path "$shellPath\sh.exe" -Target "C:\msys64\bin\sh.exe" | Out-Null
-
-# WSL is available on Windows Server 2019
-if (Test-IsWin19)
-{
-    # winbash <--> C:\Windows\System32\bash.exe
-    New-Item -ItemType SymbolicLink -Path "$shellPath\winbash.exe" -Target "$env:SystemRoot\System32\bash.exe" | Out-Null
-}
-
-# gitbash <--> C:\Program Files\Git\bin\bash.exe
-New-Item -ItemType SymbolicLink -Path "$shellPath\gitbash.exe" -Target "$env:ProgramFiles\Git\bin\bash.exe" | Out-Null
-
-# msysbash <--> C:\msys64\usr\bin\bash.exe
-New-Item -ItemType SymbolicLink -Path "$shellPath\msysbash.exe" -Target "C:\msys64\usr\bin\bash.exe" | Out-Null
-
-# Add shells to PATH
-Add-MachinePathItem $shellPath
\ No newline at end of file
diff --git a/images/win/scripts/Installers/Finalize-VM.ps1 b/images/win/scripts/Installers/Finalize-VM.ps1
index d0bb3d26..8e29dbe2 100644
--- a/images/win/scripts/Installers/Finalize-VM.ps1
+++ b/images/win/scripts/Installers/Finalize-VM.ps1
@@ -33,4 +33,8 @@ Remove-Item $profile.AllUsersAllHosts -Force
 
 # Clean yarn and npm cache
 yarn cache clean
-npm cache clean --force
\ No newline at end of file
+npm cache clean --force
+
+# allow msi to write to temp folder
+# see https://github.com/actions/virtual-environments/issues/1704
+icacls "C:\Windows\Temp" /q /c /t /grant Users:F /T
diff --git a/images/win/scripts/Installers/Install-Git.ps1 b/images/win/scripts/Installers/Install-Git.ps1
index 6c89250e..27a61969 100644
--- a/images/win/scripts/Installers/Install-Git.ps1
+++ b/images/win/scripts/Installers/Install-Git.ps1
@@ -26,7 +26,7 @@ Install-Binary  -Url $downloadUrl `
                     "/SP-", `
                     "/CLOSEAPPLICATIONS", `
                     "/RESTARTAPPLICATIONS", `
-                    "/o:PathOption=Cmd", `
+                    "/o:PathOption=CmdTools", `
                     "/o:BashTerminalOption=ConHost", `
                     "/o:EnableSymlinks=Enabled", `
                     "/COMPONENTS=gitlfs")
@@ -36,5 +36,15 @@ Choco-Install -PackageName hub
 # Disable GCM machine-wide
 [Environment]::SetEnvironmentVariable("GCM_INTERACTIVE", "Never", [System.EnvironmentVariableTarget]::Machine)
 
+Add-MachinePathItem "C:\Program Files\Git\bin"
+
+if (Test-IsWin16) {
+    $env:Path += ";$env:ProgramFiles\Git\usr\bin\"
+}
+
+# Add well-known SSH host keys to ssh_known_hosts
+ssh-keyscan -t rsa github.com >> "C:\Program Files\Git\etc\ssh\ssh_known_hosts"
+ssh-keyscan -t rsa ssh.dev.azure.com >> "C:\Program Files\Git\etc\ssh\ssh_known_hosts"
+
 Invoke-PesterTests -TestFile "Git" -TestName "Git"
 Invoke-PesterTests -TestFile "CLI.Tools" -TestName "Hub CLI"
diff --git a/images/win/scripts/Installers/Install-Mingw64.ps1 b/images/win/scripts/Installers/Install-Mingw64.ps1
index 2b999f45..b6c86048 100644
--- a/images/win/scripts/Installers/Install-Mingw64.ps1
+++ b/images/win/scripts/Installers/Install-Mingw64.ps1
@@ -7,7 +7,7 @@ Choco-Install -PackageName mingw
 
 # Make a copy of mingw32-make.exe to make.exe, which is a more discoverable name
 # and so the same command line can be used on Windows as on macOS and Linux
-$path = Get-Command mingw32-make.exe -CommandType All | Where-Object { $_.Path.Contains("C:\ProgramData\Chocolatey") } | Get-Item
+$path = where.exe mingw32-make.exe | Get-Item
 Copy-Item -Path $path -Destination (Join-Path $path.Directory 'make.exe')
 
 Invoke-PesterTests -TestFile "Tools" -TestName "Mingw64"
diff --git a/images/win/scripts/Installers/Install-Msys2.ps1 b/images/win/scripts/Installers/Install-Msys2.ps1
index 26a61e39..f0da3850 100644
--- a/images/win/scripts/Installers/Install-Msys2.ps1
+++ b/images/win/scripts/Installers/Install-Msys2.ps1
@@ -9,19 +9,35 @@
 
 $dash = "-" * 40
 
-# Downloading msys2
-$msys2Release = "https://api.github.com/repos/msys2/msys2-installer/releases/latest"
-$msys2Uri = ((Invoke-RestMethod $msys2Release).assets | Where-Object {
-  $_.name -match "x86_64" -and $_.name.EndsWith("sfx.exe") }).browser_download_url
-$msys2File = Start-DownloadWithRetry -Url $msys2Uri
+$origPath = $env:PATH
+$gitPath  = "$env:ProgramFiles\Git"
 
-# extract sfx.exe to C:\
+$msys2_release = "https://api.github.com/repos/msys2/msys2-installer/releases/latest"
+
+$msys2Uri = ((Invoke-RestMethod $msys2_release).assets | Where-Object {
+  $_.name -match "x86_64" -and $_.name.EndsWith("tar.xz") }).browser_download_url
+
+# Download the latest msys2 x86_64, filename includes release date
+Write-Host "Starting msys2 download using $($msys2Uri.split('/')[-1])"
+$msys2File = Start-DownloadWithRetry -Url $msys2Uri
+Write-Host "Finished download"
+
+# nix style path for tar
+$msys2FileU = "/$msys2File".replace(':', '').replace('\', '/')
+
+# Git tar needs exe's from mingw64\bin
+$env:PATH = "$gitPath\usr\bin;$gitPath\mingw64\bin;$origPath"
+
+$tar = "$gitPath\usr\bin\tar.exe"
+
+# extract tar.xz to C:\
 Write-Host "Starting msys2 extraction"
-& $msys2File -y -oC:\
+&$tar -xJf $msys2FileU -C /c/
+Remove-Item $msys2File
 Write-Host "Finished extraction"
 
 # Add msys2 bin tools folders to PATH temporary
-$env:PATH = "C:\msys64\mingw64\bin;C:\msys64\usr\bin;$env:PATH"
+$env:PATH = "C:\msys64\mingw64\bin;C:\msys64\usr\bin;$origPath"
 
 Write-Host "`n$dash bash pacman-key --init"
 bash.exe -c "pacman-key --init 2>&1"
@@ -57,10 +73,6 @@ Write-Host "`n$dash Install mingw32 packages"
 $pre = "mingw-w64-i686-"
 pacman.exe -S --noconfirm --needed --noprogressbar $tools32.replace('___', $pre).split(' ')
 
-# install openssh
-Write-Host "`n$dash Install openssh package"
-pacman.exe -S --noconfirm --needed --noprogressbar openssh
-
 # clean all packages to decrease image size
 Write-Host "`n$dash Clean packages"
 pacman.exe -Scc --noconfirm
@@ -76,29 +88,4 @@ pacman.exe -Q | grep -v ^mingw-w64-
 
 Write-Host "`nMSYS2 installation completed"
 
-# Environment
-# add C:\msys64\mingw64\bin and C:\msys64\usr\bin to PATH
-# C:\msys64\mingw64\bin add after C:\Windows\System32 to not replace built-in tar.exe
-$regEnvKey = 'HKLM:\SYSTEM\CurrentControlSet\Control\Session Manager\Environment\'
-$pathValue = Get-ItemPropertyValue -Path $regEnvKey -Name 'Path'
-$pathValue += ";C:\msys64\mingw64\bin;C:\msys64\usr\bin"
-Set-ItemProperty -Path $regEnvKey -Name 'Path' -Value $pathValue
-
-# Add well-known SSH host keys to ssh_known_hosts to Msys2
-ssh-keyscan -t rsa github.com >> "C:\msys64\etc\ssh\ssh_known_hosts"
-ssh-keyscan -t rsa ssh.dev.azure.com >> "C:\msys64\etc\ssh\ssh_known_hosts"
-
-# Add well-known SSH host keys to ssh_known_hosts to Git
-if (Test-Path "C:\Program Files\Git\etc\ssh")
-{
-  ssh-keyscan -t rsa github.com >> "C:\Program Files\Git\etc\ssh\ssh_known_hosts"
-  ssh-keyscan -t rsa ssh.dev.azure.com >> "C:\Program Files\Git\etc\ssh\ssh_known_hosts"
-}
-
-# Copy bash wrapper from git
-$wrapperPath = "C:\msys64\bin"
-New-Item -Path $wrapperPath -ItemType Directory -Force | Out-Null
-Copy-Item -Path "$env:ProgramFiles\Git\bin\bash.exe" -Destination $wrapperPath
-Copy-Item -Path "$env:ProgramFiles\Git\bin\sh.exe" -Destination $wrapperPath
-
 Invoke-PesterTests -TestFile "MSYS2"
diff --git a/images/win/scripts/Installers/Install-Pipx.ps1 b/images/win/scripts/Installers/Install-Pipx.ps1
new file mode 100644
index 00000000..a78cf456
--- /dev/null
+++ b/images/win/scripts/Installers/Install-Pipx.ps1
@@ -0,0 +1,14 @@
+#   Set custom directorys for pipx
+$env:PIPX_BIN_DIR = "${env:ProgramFiles(x86)}\pipx_bin"
+$env:PIPX_HOME = "${env:ProgramFiles(x86)}\pipx"
+
+#   Install pipx
+pip install pipx
+
+#   Set environment variables
+Add-MachinePathItem "${env:PIPX_BIN_DIR}"
+Set-SystemVariable -SystemVariable PIPX_BIN_DIR -Value $env:PIPX_BIN_DIR
+Set-SystemVariable -SystemVariable PIPX_HOME -Value $env:PIPX_HOME
+
+#   Test pipx
+Invoke-PesterTests -TestFile "Tools" -TestName "Pipx"
\ No newline at end of file
diff --git a/images/win/scripts/Installers/Install-PipxPackages.ps1 b/images/win/scripts/Installers/Install-PipxPackages.ps1
new file mode 100644
index 00000000..e83f5add
--- /dev/null
+++ b/images/win/scripts/Installers/Install-PipxPackages.ps1
@@ -0,0 +1,12 @@
+$pipxToolset = (Get-ToolsetContent).pipx
+foreach($tool in $pipxToolset) {
+    if ($tool.python) {
+        $pythonPath = (Get-Item  -Path "${env:AGENT_TOOLSDIRECTORY}\Python\${tool.python}.*\x64\python-${tool.python}*").FullName
+        Write-Host "Install ${tool.package} into python ${tool.python}"
+        pipx install $tool.package --python $pythonPath
+    } else {
+        Write-Host "Install ${tool.package} into default python"
+        pipx install $tool.package
+    }
+}
+Invoke-PesterTests -TestFile "PipxPackages"
\ No newline at end of file
diff --git a/images/win/scripts/Installers/Install-YAMLLint.ps1 b/images/win/scripts/Installers/Install-YAMLLint.ps1
deleted file mode 100644
index 1ebc09a3..00000000
--- a/images/win/scripts/Installers/Install-YAMLLint.ps1
+++ /dev/null
@@ -1,3 +0,0 @@
-pip install yamllint
-
-Invoke-PesterTests -TestFile "Tools" -TestName "yamllint"
\ No newline at end of file
diff --git a/images/win/scripts/SoftwareReport/SoftwareReport.Common.psm1 b/images/win/scripts/SoftwareReport/SoftwareReport.Common.psm1
index 0ca95ee7..be9603f6 100644
--- a/images/win/scripts/SoftwareReport/SoftwareReport.Common.psm1
+++ b/images/win/scripts/SoftwareReport/SoftwareReport.Common.psm1
@@ -262,6 +262,17 @@ function Get-CachedDockerImages {
     return (docker images --digests --format "* {{.Repository}}:{{.Tag}}").Split("*") | Where-Object { $_ }
 }
 
+function Get-CachedDockerImagesTableData {
+    return (docker images --digests --format "*{{.Repository}}:{{.Tag}}|{{.Digest}} |{{.CreatedAt}}").Split("*")     | Where-Object { $_ } |  ForEach-Object {
+      $parts=$_.Split("|")
+      [PSCustomObject] @{
+             "Repository:Tag" = $parts[0]
+              "Digest" = $parts[1]
+              "Created" = $parts[2].split(' ')[0]
+         }
+    }
+}
+
 function Get-PacmanVersion {
     $msys2BinDir = "C:\msys64\usr\bin"
     $pacmanPath = Join-Path $msys2BinDir "pacman.exe"
@@ -271,13 +282,11 @@ function Get-PacmanVersion {
     return "- Pacman $pacmanVersion"
 }
 
-function Get-ShellTarget {
-    $shells = Get-ChildItem C:\shells -File | Select-Object @{n="Name";e={
-        $name = $_.Name
-        if ($name -eq 'bash.exe') {"$name (Default)"} else {$name}}},@{n="Target";e={@($_.Target)[0]}} | Sort-Object Name
-    $shells | New-MDTable -Columns ([ordered]@{Name = "left"; Target = "left";})
-}
-
 function Get-YAMLLintVersion {
     yamllint --version
-}
\ No newline at end of file
+}
+
+function Get-PipxVersion {
+    $pipxVersion = pipx --version
+    return "Pipx $pipxVersion"
+}
diff --git a/images/win/scripts/SoftwareReport/SoftwareReport.Generator.ps1 b/images/win/scripts/SoftwareReport/SoftwareReport.Generator.ps1
index 06e1054d..91c19dc6 100644
--- a/images/win/scripts/SoftwareReport/SoftwareReport.Generator.ps1
+++ b/images/win/scripts/SoftwareReport/SoftwareReport.Generator.ps1
@@ -59,7 +59,8 @@ $markdown += New-MDList -Style Unordered -Lines @(
     (Get-RubyGemsVersion),
     (Get-HelmVersion),
     (Get-ComposerVersion),
-    (Get-NugetVersion)
+    (Get-NugetVersion),
+    (Get-PipxVersion)
 )
 
 $markdown += New-MDHeader "Project Management" -Level 3
@@ -142,22 +143,14 @@ $markdown += New-MDList -Style Unordered -Lines @(
     (Get-SeleniumWebDriverVersion -Driver "iexplorer")
 )
 
-$markdown += New-MDHeader "Shells" -Level 3
-$markdown += Get-ShellTarget
-$markdown += New-MDNewLine
-
 $markdown += New-MDHeader "MSYS2" -Level 3
 $markdown += Get-PacmanVersion
 $markdown += New-MDNewLine
-$markdown += New-MDHeader "Notes:" -Level 5
 $markdown += @'
 ```
 Location: C:\msys64
 
-1. MSYS2 is pre-installed on image
-2. C:\msys64\mingw64\bin is added to PATH and has lower precedence than C:\Windows\System32
-3. C:\msys64\usr\bin is added to PATH and has lower precedence than C:\Windows\System32
-4. Default bash.exe shell is set to the C:\msys64\usr\bin\bash.exe
+Note: MSYS2 is pre-installed on image but not added to PATH.
 ```
 '@
 $markdown += New-MDNewLine
@@ -243,6 +236,7 @@ $markdown += New-MDNewLine
 
 # Docker images section
 $markdown += New-MDHeader "Cached Docker images" -Level 3
-$markdown += New-MDList -Style Unordered -Lines @(Get-CachedDockerImages)
+$markdown += Get-CachedDockerImagesTableData | New-MDTable
+$markdown += New-MDNewLine
 
-$markdown | Out-File -FilePath "C:\InstalledSoftware.md"
\ No newline at end of file
+$markdown | Out-File -FilePath "C:\InstalledSoftware.md"
diff --git a/images/win/scripts/Tests/Git.Tests.ps1 b/images/win/scripts/Tests/Git.Tests.ps1
index e7675ee0..8dd159fa 100644
--- a/images/win/scripts/Tests/Git.Tests.ps1
+++ b/images/win/scripts/Tests/Git.Tests.ps1
@@ -1,5 +1,5 @@
 Describe "Git" {
-    $gitTools = 'git', 'git-lfs'
+    $gitTools = 'bash', 'awk', 'git', 'git-lfs'
     $gitTestCases = $gitTools | ForEach-Object {
         @{
             toolName = $_
diff --git a/images/win/scripts/Tests/PipxPackages.Tests.ps1 b/images/win/scripts/Tests/PipxPackages.Tests.ps1
new file mode 100644
index 00000000..41041078
--- /dev/null
+++ b/images/win/scripts/Tests/PipxPackages.Tests.ps1
@@ -0,0 +1,7 @@
+Describe "PipxPackages" {
+    $pipxToolset = (Get-ToolsetContent).pipx
+    $testCases = $pipxToolset | ForEach-Object { @{package = $_.package; cmd = $_.cmd} }
+    It "<package>" -TestCases $testCases {
+        "$cmd" | Should -ReturnZeroExitCode
+    }
+}
\ No newline at end of file
diff --git a/images/win/scripts/Tests/Shell.Tests.ps1 b/images/win/scripts/Tests/Shell.Tests.ps1
deleted file mode 100644
index 084f40ca..00000000
--- a/images/win/scripts/Tests/Shell.Tests.ps1
+++ /dev/null
@@ -1,50 +0,0 @@
-Describe "Shell" {
-    $shellTestCases = @(
-        @{Name = "C:\shells\bash.exe"; Target = "C:\msys64\bin\bash.exe"},
-        @{Name = "C:\shells\sh.exe"; Target = "C:\msys64\bin\sh.exe"},
-        @{Name = "C:\shells\gitbash.exe"; Target = "$env:ProgramFiles\Git\bin\bash.exe"},
-        @{Name = "C:\shells\msysbash.exe"; Target = "C:\msys64\usr\bin\bash.exe"}
-    )
-
-    $pathTestCases = @(
-        @{Path = "C:\shells"},
-        @{Path = "C:\msys64\mingw64\bin"},
-        @{Path = "C:\msys64\usr\bin"}
-    )
-
-    $IsWin16 = Test-IsWin16
-
-    It "Default bash.exe from MSYS2" {
-        (Get-Command bash).Path | Should -BeExactly "C:\shells\bash.exe"
-    }
-
-    It "Default sh.exe from MSYS2" {
-        (Get-Command sh).Path | Should -BeExactly "C:\shells\sh.exe"
-    }
-
-    It "Folder C:\shells exists" {
-        "C:\shells" | Should -Exist
-    }
-
-    It "C:\Windows\System32 before C:\msys64\mingw64\bin and C:\msys64\usr\bin" {
-        $path = $env:Path.Split(";").ToLower()
-        $indexOfSystem32 = $path.IndexOf("c:\windows\system32")
-
-        $path.IndexOf("c:\msys64\mingw64\bin") | Should -BeGreaterThan $indexOfSystem32
-        $path.IndexOf("c:\msys64\usr\bin") | Should -BeGreaterThan $indexOfSystem32
-    }
-
-    It "C:\shells\winbash.exe target to $env:SystemRoot\System32\bash.exe" -Skip:$IsWin16 {
-        $Name = "C:\shells\winbash.exe"
-        $Target = "$env:SystemRoot\System32\bash.exe"
-        (Get-Item $Name).Target | Should -BeExactly $Target
-    }
-
-    It "<Name> target to <Target>" -TestCases $shellTestCases {
-        (Get-Item $Name).Target | Should -BeExactly $Target
-    }
-
-    It "<Path> is in PATH" -TestCases $pathTestCases {
-        $env:Path.Split(";") | Should -Contain $Path
-    }
-}
\ No newline at end of file
diff --git a/images/win/scripts/Tests/Tools.Tests.ps1 b/images/win/scripts/Tests/Tools.Tests.ps1
index cbb0609a..a0024532 100644
--- a/images/win/scripts/Tests/Tools.Tests.ps1
+++ b/images/win/scripts/Tests/Tools.Tests.ps1
@@ -214,12 +214,6 @@ Describe "ServiceFabricSDK" {
     }
 }
 
-Describe "yamllint" {
-    It "yamllint" {
-        "yamllint --version" | Should -ReturnZeroExitCode
-    }
-}
-
 Describe "Svn" {
     It "svn" {
         "svn --version --quiet" | Should -ReturnZeroExitCode
@@ -269,3 +263,9 @@ Describe "Zstd" {
         "zstd -V" | Should -ReturnZeroExitCode
     }
 }
+
+Describe "Pipx" {
+    It "Pipx" {
+        "pipx --version" | Should -ReturnZeroExitCode
+    }
+}
diff --git a/images/win/toolsets/toolset-2016.json b/images/win/toolsets/toolset-2016.json
index fef0a3fc..f5d30694 100644
--- a/images/win/toolsets/toolset-2016.json
+++ b/images/win/toolsets/toolset-2016.json
@@ -73,7 +73,6 @@
             "platform" : "win32",
             "toolset": "msvc14.1",
             "versions": [
-                "1.69.0",
                 "1.72.0"
             ]
         }
@@ -238,5 +237,11 @@
             "mcr.microsoft.com/dotnet/framework/runtime:4.8-windowsservercore-ltsc2016",
             "microsoft/aspnetcore-build:1.0-2.0"
         ]
-    }
+    },
+    "pipx": [
+        {
+            "package": "yamllint",
+            "cmd": "yamllint --version"
+        }
+    ]
 }
diff --git a/images/win/toolsets/toolset-2019.json b/images/win/toolsets/toolset-2019.json
index c76c9701..ebb7aa82 100644
--- a/images/win/toolsets/toolset-2019.json
+++ b/images/win/toolsets/toolset-2019.json
@@ -66,16 +66,6 @@
             ],
             "default": "1.14.*"
         },
-        {
-            "name": "Boost",
-            "url" : "https://raw.githubusercontent.com/actions/boost-versions/main/versions-manifest.json",
-            "arch": "x86_64",
-            "platform" : "win32",
-            "toolset": "msvc14.1",
-            "versions": [
-                "1.69.0"
-            ]
-        },
         {
             "name": "Boost",
             "url" : "https://raw.githubusercontent.com/actions/boost-versions/main/versions-manifest.json",
@@ -290,5 +280,11 @@
             "mcr.microsoft.com/dotnet/framework/runtime:4.8-windowsservercore-ltsc2019",
             "microsoft/aspnetcore-build:1.0-2.0"
         ]
-    }
+    },
+    "pipx": [
+        {
+            "package": "yamllint",
+            "cmd": "yamllint --version"
+        }
+    ]
 }
diff --git a/images/win/windows2016.json b/images/win/windows2016.json
index 8c1314d6..120e7ac9 100644
--- a/images/win/windows2016.json
+++ b/images/win/windows2016.json
@@ -235,8 +235,9 @@
                 "{{ template_dir }}/scripts/Installers/Install-PyPy.ps1",
                 "{{ template_dir }}/scripts/Installers/Install-Toolset.ps1",
                 "{{ template_dir }}/scripts/Installers/Configure-Toolset.ps1",
-                "{{ template_dir }}/scripts/Installers/Install-YAMLLint.ps1",
-                "{{ template_dir }}/scripts/Installers/Update-AndroidSDK.ps1"
+                "{{ template_dir }}/scripts/Installers/Update-AndroidSDK.ps1",
+                "{{ template_dir }}/scripts/Installers/Install-Pipx.ps1",
+                "{{ template_dir }}/scripts/Installers/Install-PipxPackages.ps1"
             ]
         },
         {
@@ -332,8 +333,7 @@
             "type": "powershell",
             "scripts": [
                 "{{ template_dir }}/scripts/Installers/Install-WindowsUpdates.ps1",
-                "{{ template_dir }}/scripts/Installers/Configure-DynamicPort.ps1",
-                "{{ template_dir }}/scripts/Installers/Configure-Shell.ps1"
+                "{{ template_dir }}/scripts/Installers/Configure-DynamicPort.ps1"
             ],
             "elevated_user": "{{user `install_user`}}",
             "elevated_password": "{{user `install_password`}}"
diff --git a/images/win/windows2019.json b/images/win/windows2019.json
index a002f77f..a27bf27d 100644
--- a/images/win/windows2019.json
+++ b/images/win/windows2019.json
@@ -249,9 +249,10 @@
                 "{{ template_dir }}/scripts/Installers/Install-PyPy.ps1",
                 "{{ template_dir }}/scripts/Installers/Install-Toolset.ps1",
                 "{{ template_dir }}/scripts/Installers/Configure-Toolset.ps1",
-                "{{ template_dir }}/scripts/Installers/Install-YAMLLint.ps1",
                 "{{ template_dir }}/scripts/Installers/Update-AndroidSDK.ps1",
-                "{{ template_dir }}/scripts/Installers/Install-AzureModules.ps1"
+                "{{ template_dir }}/scripts/Installers/Install-AzureModules.ps1",
+                "{{ template_dir }}/scripts/Installers/Install-Pipx.ps1",
+                "{{ template_dir }}/scripts/Installers/Install-PipxPackages.ps1"
             ]
         },
         {
@@ -330,8 +331,7 @@
             "type": "powershell",
             "scripts": [
                 "{{ template_dir }}/scripts/Installers/Install-WindowsUpdates.ps1",
-                "{{ template_dir }}/scripts/Installers/Configure-DynamicPort.ps1",
-                "{{ template_dir }}/scripts/Installers/Configure-Shell.ps1"
+                "{{ template_dir }}/scripts/Installers/Configure-DynamicPort.ps1"
             ],
             "elevated_user": "{{user `install_user`}}",
             "elevated_password": "{{user `install_password`}}"