diff --git a/images/win/scripts/Installers/Configure-Shell.ps1 b/images/win/scripts/Installers/Configure-Shell.ps1
new file mode 100644
index 000000000..8eb163bcf
--- /dev/null
+++ b/images/win/scripts/Installers/Configure-Shell.ps1
@@ -0,0 +1,23 @@
+# 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\usr\bin\bash.exe" | Out-Null
+New-Item -ItemType SymbolicLink -Path "$shellPath\sh.exe" -Target "C:\msys64\usr\bin\sh.exe" | Out-Null
+
+# WSL is available on Windows Server 2019
+if (Test-IsWin19)
+{
+    # winbash <--> C:\Windows\System32\bash.exe
+    New-Item -ItemType SymbolicLink -Path "$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/Install-Git.ps1 b/images/win/scripts/Installers/Install-Git.ps1
index 27a619695..6c89250e9 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=CmdTools", `
+                    "/o:PathOption=Cmd", `
                     "/o:BashTerminalOption=ConHost", `
                     "/o:EnableSymlinks=Enabled", `
                     "/COMPONENTS=gitlfs")
@@ -36,15 +36,5 @@ 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 b6c860485..2b999f450 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
-$path = where.exe mingw32-make.exe | Get-Item
+$path = Get-Command mingw32-make.exe -CommandType All | Where-Object { $_.Path.Contains("C:\ProgramData\Chocolatey") } | 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 f0da38503..dea3b95d0 100644
--- a/images/win/scripts/Installers/Install-Msys2.ps1
+++ b/images/win/scripts/Installers/Install-Msys2.ps1
@@ -9,35 +9,19 @@
 
 $dash = "-" * 40
 
-$origPath = $env:PATH
-$gitPath  = "$env:ProgramFiles\Git"
-
-$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])"
+# 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
-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:\
+# extract sfx.exe to C:\
 Write-Host "Starting msys2 extraction"
-&$tar -xJf $msys2FileU -C /c/
-Remove-Item $msys2File
+& $msys2File -y -oC:\
 Write-Host "Finished extraction"
 
 # Add msys2 bin tools folders to PATH temporary
-$env:PATH = "C:\msys64\mingw64\bin;C:\msys64\usr\bin;$origPath"
+$env:PATH = "C:\msys64\mingw64\bin;C:\msys64\usr\bin;$env:PATH"
 
 Write-Host "`n$dash bash pacman-key --init"
 bash.exe -c "pacman-key --init 2>&1"
@@ -73,6 +57,10 @@ Write-Host "`n$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
@@ -88,4 +76,23 @@ 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"
+}
+
 Invoke-PesterTests -TestFile "MSYS2"
diff --git a/images/win/scripts/SoftwareReport/SoftwareReport.Common.psm1 b/images/win/scripts/SoftwareReport/SoftwareReport.Common.psm1
index 05b101aac..0ca95ee71 100644
--- a/images/win/scripts/SoftwareReport/SoftwareReport.Common.psm1
+++ b/images/win/scripts/SoftwareReport/SoftwareReport.Common.psm1
@@ -271,6 +271,13 @@ 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
diff --git a/images/win/scripts/SoftwareReport/SoftwareReport.Generator.ps1 b/images/win/scripts/SoftwareReport/SoftwareReport.Generator.ps1
index 1b3bf299a..06e1054da 100644
--- a/images/win/scripts/SoftwareReport/SoftwareReport.Generator.ps1
+++ b/images/win/scripts/SoftwareReport/SoftwareReport.Generator.ps1
@@ -142,14 +142,22 @@ $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
 
-Note: MSYS2 is pre-installed on image but not added to PATH.
+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
 ```
 '@
 $markdown += New-MDNewLine
diff --git a/images/win/scripts/Tests/Git.Tests.ps1 b/images/win/scripts/Tests/Git.Tests.ps1
index 8dd159fa4..e7675ee07 100644
--- a/images/win/scripts/Tests/Git.Tests.ps1
+++ b/images/win/scripts/Tests/Git.Tests.ps1
@@ -1,5 +1,5 @@
 Describe "Git" {
-    $gitTools = 'bash', 'awk', 'git', 'git-lfs'
+    $gitTools = 'git', 'git-lfs'
     $gitTestCases = $gitTools | ForEach-Object {
         @{
             toolName = $_
diff --git a/images/win/scripts/Tests/Shell.Tests.ps1 b/images/win/scripts/Tests/Shell.Tests.ps1
new file mode 100644
index 000000000..915940e2a
--- /dev/null
+++ b/images/win/scripts/Tests/Shell.Tests.ps1
@@ -0,0 +1,50 @@
+Describe "Shell" {
+    $shellTestCases = @(
+        @{Name = "C:\shells\bash.exe"; Target = "C:\msys64\usr\bin\bash.exe"},
+        @{Name = "C:\shells\sh.exe"; Target = "C:\msys64\usr\bin\sh.exe"},
+        @{Name = "C:\shells\gitbash.exe"; Target = "$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/windows2016.json b/images/win/windows2016.json
index 3c4b65663..8c1314d63 100644
--- a/images/win/windows2016.json
+++ b/images/win/windows2016.json
@@ -332,7 +332,8 @@
             "type": "powershell",
             "scripts": [
                 "{{ template_dir }}/scripts/Installers/Install-WindowsUpdates.ps1",
-                "{{ template_dir }}/scripts/Installers/Configure-DynamicPort.ps1"
+                "{{ template_dir }}/scripts/Installers/Configure-DynamicPort.ps1",
+                "{{ template_dir }}/scripts/Installers/Configure-Shell.ps1"
             ],
             "elevated_user": "{{user `install_user`}}",
             "elevated_password": "{{user `install_password`}}"
diff --git a/images/win/windows2019.json b/images/win/windows2019.json
index 6b9f3a868..a002f77f5 100644
--- a/images/win/windows2019.json
+++ b/images/win/windows2019.json
@@ -330,7 +330,8 @@
             "type": "powershell",
             "scripts": [
                 "{{ template_dir }}/scripts/Installers/Install-WindowsUpdates.ps1",
-                "{{ template_dir }}/scripts/Installers/Configure-DynamicPort.ps1"
+                "{{ template_dir }}/scripts/Installers/Configure-DynamicPort.ps1",
+                "{{ template_dir }}/scripts/Installers/Configure-Shell.ps1"
             ],
             "elevated_user": "{{user `install_user`}}",
             "elevated_password": "{{user `install_password`}}"