diff --git a/images/win/scripts/Installers/Initialize-VM.ps1 b/images/win/scripts/Installers/Initialize-VM.ps1
index 0277287276c0..26ce2a4ec463 100644
--- a/images/win/scripts/Installers/Initialize-VM.ps1
+++ b/images/win/scripts/Installers/Initialize-VM.ps1
@@ -33,6 +33,10 @@ function Disable-UserAccessControl {
 # Enable $ErrorActionPreference='Stop' for AllUsersAllHosts
 Add-Content -Path $profile.AllUsersAllHosts -Value '$ErrorActionPreference="Stop"'
 
+# Set static env vars
+setx ImageVersion $env:IMAGE_VERSION /m
+setx ImageOS $env:IMAGE_OS /m
+
 # Set TLS1.2
 [Net.ServicePointManager]::SecurityProtocol = [Net.ServicePointManager]::SecurityProtocol -bor "Tls12"
 
diff --git a/images/win/scripts/SoftwareReport/SoftwareReport.Generator.ps1 b/images/win/scripts/SoftwareReport/SoftwareReport.Generator.ps1
index 9bdd4a704229..3203c5bf92ce 100644
--- a/images/win/scripts/SoftwareReport/SoftwareReport.Generator.ps1
+++ b/images/win/scripts/SoftwareReport/SoftwareReport.Generator.ps1
@@ -17,7 +17,7 @@ $markdown += New-MDHeader "$OSName" -Level 1
 $OSVersion = Get-OSVersion
 $markdown += New-MDList -Style Unordered -Lines @(
     "$OSVersion"
-    "Image Version: $env:ImageVersion"
+    "Image Version: $env:IMAGE_VERSION"
 )
 
 if (Test-IsWin19)
diff --git a/images/win/windows2016.json b/images/win/windows2016.json
index 9383a2a17a59..f7762385bf2c 100644
--- a/images/win/windows2016.json
+++ b/images/win/windows2016.json
@@ -112,7 +112,8 @@
         {
             "type": "powershell",
             "environment_vars": [
-                "ImageVersion={{user `image_version`}}",
+                "IMAGE_VERSION={{user `image_version`}}",
+                "IMAGE_OS={{user `image_os`}}",
                 "TOOLSET_JSON_PATH={{user `toolset_json_path`}}",
                 "PSMODULES_ROOT_FOLDER={{user `psmodules_root_folder`}}"
             ],
@@ -134,13 +135,6 @@
             "type": "windows-restart",
             "restart_timeout": "30m"
         },
-        {
-            "type": "powershell",
-            "inline": [
-                "setx ImageVersion {{user `image_version` }} /m",
-                "setx ImageOS {{user `image_os` }} /m"
-            ]
-        },
         {
             "type": "powershell",
             "environment_vars": [
@@ -357,6 +351,7 @@
                 "pwsh -File '{{user `image_folder`}}\\SoftwareReport\\SoftwareReport.Generator.ps1'"
             ],
             "environment_vars": [
+                "IMAGE_VERSION={{user `image_version`}}",
                 "TOOLSET_JSON_PATH={{user `toolset_json_path`}}"
             ]
         },
diff --git a/images/win/windows2019.json b/images/win/windows2019.json
index 39b58c003a66..24e1ec6406a6 100644
--- a/images/win/windows2019.json
+++ b/images/win/windows2019.json
@@ -112,7 +112,8 @@
         {
             "type": "powershell",
             "environment_vars": [
-                "ImageVersion={{user `image_version`}}",
+                "IMAGE_VERSION={{user `image_version`}}",
+                "IMAGE_OS={{user `image_os`}}",
                 "TOOLSET_JSON_PATH={{user `toolset_json_path`}}",
                 "PSMODULES_ROOT_FOLDER={{user `psmodules_root_folder`}}"
             ],
@@ -138,13 +139,6 @@
                 "{{ template_dir }}/scripts/Installers/Install-ContainersFeature.ps1"
             ]
         },
-        {
-            "type": "powershell",
-            "inline": [
-                "setx ImageVersion {{user `image_version` }} /m",
-                "setx ImageOS {{user `image_os` }} /m"
-            ]
-        },
         {
             "type": "windows-restart",
             "restart_timeout": "10m"
@@ -350,6 +344,7 @@
                 "pwsh -File '{{user `image_folder`}}\\SoftwareReport\\SoftwareReport.Generator.ps1'"
             ],
             "environment_vars": [
+                "IMAGE_VERSION={{user `image_version`}}",
                 "TOOLSET_JSON_PATH={{user `toolset_json_path`}}"
             ]
         },