diff --git a/images/win/Windows2016-Azure.json b/images/win/Windows2016-Azure.json
index 34c1abcb3..d65286497 100644
--- a/images/win/Windows2016-Azure.json
+++ b/images/win/Windows2016-Azure.json
@@ -82,6 +82,11 @@
             "source": "{{ template_dir }}/scripts/SoftwareReport",
             "destination": "{{user `image_folder`}}"
         },
+        {
+            "type": "file",
+            "source": "{{ template_dir }}/post-generation",
+            "destination": "C:/post-generation"
+        },
         {
             "type": "file",
             "source": "{{ template_dir }}/scripts/Tests",
diff --git a/images/win/Windows2019-Azure.json b/images/win/Windows2019-Azure.json
index 10b6e5dc1..445a5968d 100644
--- a/images/win/Windows2019-Azure.json
+++ b/images/win/Windows2019-Azure.json
@@ -82,6 +82,11 @@
             "source": "{{ template_dir }}/scripts/SoftwareReport",
             "destination": "{{user `image_folder`}}"
         },
+        {
+            "type": "file",
+            "source": "{{ template_dir }}/post-generation",
+            "destination": "C:/post-generation"
+        },
         {
             "type": "file",
             "source": "{{ template_dir }}/scripts/Tests",
diff --git a/images/win/post-generation/Dotnet.ps1 b/images/win/post-generation/Dotnet.ps1
new file mode 100644
index 000000000..fd43757a6
--- /dev/null
+++ b/images/win/post-generation/Dotnet.ps1
@@ -0,0 +1,8 @@
+$latestPath = [System.Environment]::GetEnvironmentVariable('PATH', [System.EnvironmentVariableTarget]::Machine)
+$dotnetPath = "$env:USERPROFILE\.dotnet\tools"
+
+if (-not $latestPath.Contains($dotnetPath))
+{
+    $latestPath = "$dotnetPath;$latestPath"
+    [System.Environment]::SetEnvironmentVariable('PATH', $latestPath, [System.EnvironmentVariableTarget]::Machine)
+}
\ No newline at end of file
diff --git a/images/win/post-generation/RustJunction.ps1 b/images/win/post-generation/RustJunction.ps1
new file mode 100644
index 000000000..86f3fc106
--- /dev/null
+++ b/images/win/post-generation/RustJunction.ps1
@@ -0,0 +1,12 @@
+# Create Rust junction points to cargo and rustup folder
+$cargoTarget = "$env:USERPROFILE\.cargo"
+if (-not (Test-Path $cargoTarget))
+{
+    New-Item -ItemType Junction -Path $cargoTarget -Target "C:\Rust\.cargo"
+}
+
+$rustupTarget = "$env:USERPROFILE\.rustup"
+if (-not (Test-Path $rustupTarget))
+{
+    New-Item -ItemType Junction -Path $rustupTarget -Target "C:\Rust\.rustup"
+}
\ No newline at end of file
diff --git a/images/win/post-generation/VSConfiguration.ps1 b/images/win/post-generation/VSConfiguration.ps1
new file mode 100644
index 000000000..0ff9d7bfb
--- /dev/null
+++ b/images/win/post-generation/VSConfiguration.ps1
@@ -0,0 +1,4 @@
+$vsInstallRoot = Get-VisualStudioPath
+$devEnvPath = "$vsInstallRoot\Common7\IDE\devenv.exe"
+
+cmd.exe /c "`"$devEnvPath`" /updateconfiguration"
\ 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 2a5ea9259..16b7ac15e 100644
--- a/images/win/scripts/Installers/Install-Git.ps1
+++ b/images/win/scripts/Installers/Install-Git.ps1
@@ -40,5 +40,10 @@ Choco-Install -PackageName hub
 
 Add-MachinePathItem "C:\Program Files\Git\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"