diff --git a/images/macos/provision/configuration/finalize-vm.sh b/images/macos/provision/configuration/finalize-vm.sh
index 6770cef5f..c3d72b7a8 100644
--- a/images/macos/provision/configuration/finalize-vm.sh
+++ b/images/macos/provision/configuration/finalize-vm.sh
@@ -13,6 +13,12 @@ if is_Catalina; then
     fi
 fi
 
+# Remove Parallels Desktop
+# https://github.com/actions/runner-images/issues/6105
+if is_Monterey; then
+    brew uninstall parallels
+fi
+
 # Put documentation to $HOME root
 cp $HOME/image-generation/output/software-report/systeminfo.txt $HOME/image-generation/output/software-report/systeminfo.md $HOME/
 
diff --git a/images/macos/provision/core/commonutils.sh b/images/macos/provision/core/commonutils.sh
index 75639dcd3..5ec148514 100644
--- a/images/macos/provision/core/commonutils.sh
+++ b/images/macos/provision/core/commonutils.sh
@@ -16,7 +16,12 @@ for package in $cask_packages; do
     brew install --cask $package
 done
 
-# Execute AppleScript to change security preferences for virtualbox
+# Load "Parallels International GmbH"
+if is_Monterey; then
+    sudo kextload /Applications/Parallels\ Desktop.app/Contents/Library/Extensions/10.9/prl_hypervisor.kext || true
+fi
+
+# Execute AppleScript to change security preferences
 # System Preferences -> Security & Privacy -> General -> Unlock -> Allow -> Not now
 if is_Monterey; then
     if is_Veertu; then
@@ -38,6 +43,26 @@ if is_Monterey; then
     osascript $HOME/utils/confirm-identified-developers.scpt $USER_PASSWORD
 fi
 
+# Validate "Parallels International GmbH" kext
+if is_Monterey; then
+    dbName="/var/db/SystemPolicyConfiguration/KextPolicy"
+    dbQuery="SELECT * FROM kext_policy WHERE bundle_id LIKE 'com.parallels.kext.%';"
+    kext=$(sudo sqlite3 $dbName "$dbQuery")
+
+    if [ -z "$kext" ]; then
+        echo "Parallels International GmbH not found"
+        exit 1
+    fi
+
+    # Create env variable
+    url=$(brew info --json=v2 --installed | jq -r '.casks[] | select(.name[] == "Parallels Desktop").url')
+    if [ -z "$url" ]; then
+        echo "Unable to parse url for Parallels Desktop cask"
+        exit 1
+    fi
+    echo "export PARALLELS_DMG_URL=$url" >> "${HOME}/.bashrc"
+fi
+
 # Invoke bazel to download bazel version via bazelisk
 bazel
 
diff --git a/images/macos/provision/utils/confirm-identified-developers.scpt b/images/macos/provision/utils/confirm-identified-developers.scpt
index a445d8be1..31a650d76 100644
--- a/images/macos/provision/utils/confirm-identified-developers.scpt
+++ b/images/macos/provision/utils/confirm-identified-developers.scpt
@@ -12,17 +12,13 @@ on run argv
   set userpassword to item 1 of argv
   set secpane to "Security & Privacy"
 
-  tell application "System Events"
-    tell security preferences
-      keystroke return
-      delay 5
-    end tell
-  end tell
-
   activate application "System Preferences"
   delay 5
+
   tell application "System Events"
     tell process "System Preferences"
+        set frontmost to true
+        delay 2
         click menu item secpane of menu "View" of menu bar 1
         delay 5
         click button 1 of window 1
diff --git a/images/macos/software-report/SoftwareReport.Common.psm1 b/images/macos/software-report/SoftwareReport.Common.psm1
index 2012f889c..01955e019 100644
--- a/images/macos/software-report/SoftwareReport.Common.psm1
+++ b/images/macos/software-report/SoftwareReport.Common.psm1
@@ -575,6 +575,20 @@ function Build-PackageManagementEnvironmentTable {
     }
 }
 
+function Build-MiscellaneousEnvironmentTable {
+    return @(
+        @{
+            "Name" = "PARALLELS_DMG_URL"
+            "Value" = $env:PARALLELS_DMG_URL
+        }
+    ) | ForEach-Object {
+        [PSCustomObject] @{
+            "Name" = $_.Name
+            "Value" = $_.Value
+        }
+    }
+}
+
 function Get-GraalVMVersion {
     $version = & "$env:GRAALVM_11_ROOT\java" --version | Select-String -Pattern "GraalVM" | Take-Part -Part 5,6
     return $version
diff --git a/images/macos/software-report/SoftwareReport.Generator.ps1 b/images/macos/software-report/SoftwareReport.Generator.ps1
index 3169e4338..433b4ec31 100644
--- a/images/macos/software-report/SoftwareReport.Generator.ps1
+++ b/images/macos/software-report/SoftwareReport.Generator.ps1
@@ -309,6 +309,21 @@ $markdown += New-MDList -Style Unordered -Lines (@(
     ) | Sort-Object
 )
 
+if ($os.IsMonterey) {
+$markdown += New-MDHeader "Environment variables" -Level 4
+$markdown += Build-MiscellaneousEnvironmentTable | New-MDTable
+$markdown += New-MDNewLine
+
+$markdown += New-MDHeader "Notes:" -Level 5
+$misc = @'
+```
+If you want to use Parallels Desktop you should download a package from URL stored in
+PARALLELS_DMG_URL environment variable. A system extension is allowed for this version.
+```
+'@
+$markdown += New-MDParagraph -Lines $misc
+}
+
 #
 # Generate systeminfo.txt with information about image (for debug purpose)
 #
diff --git a/images/macos/toolsets/toolset-12.json b/images/macos/toolsets/toolset-12.json
index b45343442..d69b6e1d2 100644
--- a/images/macos/toolsets/toolset-12.json
+++ b/images/macos/toolsets/toolset-12.json
@@ -181,7 +181,8 @@
         "cask_packages": [
             "julia",
             "vagrant",
-            "virtualbox"
+            "virtualbox",
+            "parallels"
         ]
     },
     "gcc": {