diff --git a/images/macos/helpers/Common.Helpers.psm1 b/images/macos/helpers/Common.Helpers.psm1
index f8d758b3b..0dbe23831 100644
--- a/images/macos/helpers/Common.Helpers.psm1
+++ b/images/macos/helpers/Common.Helpers.psm1
@@ -28,17 +28,14 @@ function Get-EnvironmentVariable($variable) {
 function Get-OSVersion {
     $osVersion = [Environment]::OSVersion
     $osVersionMajorMinor = $osVersion.Version.ToString(2)
-    # Monterey needs future review:
-    # [Environment]::OSVersion returns 11.0 for Monterey preview.
-    [SemVer]$osMontereyVersion = sw_vers -productVersion
     return [PSCustomObject]@{
         Version = $osVersion.Version
         Platform = $osVersion.Platform
         IsCatalina = $osVersionMajorMinor -eq "10.15"
-        IsBigSur = $osVersionMajorMinor -eq "11.0"
-        IsMonterey = $osMontereyVersion.Major -eq "12"
-        IsLessThanMonterey = $osMontereyVersion -lt "12.0"
-        IsHigherThanCatalina = [SemVer]$osVersion.Version -ge "11.0"
+        IsBigSur = $osVersion.Version.Major -eq "11"
+        IsMonterey = $osVersion.Version.Major -eq "12"
+        IsLessThanMonterey = $osVersion.Version.Major -lt "12"
+        IsHigherThanCatalina = $osVersion.Version.Major -ge "11"
     }
 }
 
diff --git a/images/macos/provision/core/commonutils.sh b/images/macos/provision/core/commonutils.sh
index f51d9b9ec..daa06627a 100644
--- a/images/macos/provision/core/commonutils.sh
+++ b/images/macos/provision/core/commonutils.sh
@@ -16,6 +16,12 @@ for package in $cask_packages; do
     brew install --cask $package
 done
 
+# Execute AppleScript to change security preferences for virtualbox
+# System Preferences -> Security & Privacy -> General -> Unlock -> Allow -> Not now
+if is_Monterey; then
+    osascript $HOME/utils/confirm-identified-developers.scpt $USER_PASSWORD
+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
new file mode 100644
index 000000000..a445d8be1
--- /dev/null
+++ b/images/macos/provision/utils/confirm-identified-developers.scpt
@@ -0,0 +1,53 @@
+# This AppleScript confirms developers in security preferences via macOS UI.
+# It uses after VirtualBox installation to add 'Oracle Inc' as identified developer.
+# Steps:
+# - Close security preferences pop-up (it can be open after VirtualBox installation)
+# - Open System Preferences -> Security & Privacy -> General
+# - Unlock security preferences with user password (button 'Click the lock to make changes')
+# - Click 'Allow' or 'Details…' button to confirm developers
+# - Click 'Not now' button on restarting pop-up
+# - Close System Preferences
+
+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"
+        click menu item secpane of menu "View" of menu bar 1
+        delay 5
+        click button 1 of window 1
+        delay 5
+        keystroke userpassword
+        delay 5
+        keystroke return
+        delay 5
+        click radio button "General" of tab group 1 of window 1
+        delay 5
+        if exists of UI element "Details…" of tab group 1 of window 1 then
+          click button "Details…" of tab group 1 of window 1
+          delay 5
+          keystroke return
+          delay 5
+          keystroke return
+          delay 5
+        end if
+        if exists of UI element "Allow" of tab group 1 of window 1 then
+          click button "Allow" of tab group 1 of window 1
+          delay 5
+          keystroke return
+          delay 5
+        end if
+        click button 5 of window 1
+    end tell
+  end tell
+end run
\ No newline at end of file
diff --git a/images/macos/software-report/SoftwareReport.Common.psm1 b/images/macos/software-report/SoftwareReport.Common.psm1
index d4cf17e32..c2dc9234d 100644
--- a/images/macos/software-report/SoftwareReport.Common.psm1
+++ b/images/macos/software-report/SoftwareReport.Common.psm1
@@ -389,7 +389,7 @@ function Get-NewmanVersion {
 
 function Get-VirtualBoxVersion {
     $virtualBox = Run-Command "vboxmanage -v"
-    return "virtualbox $virtualBox"
+    return "VirtualBox $virtualBox"
 }
 
 function Get-VagrantVersion {
diff --git a/images/macos/software-report/SoftwareReport.Generator.ps1 b/images/macos/software-report/SoftwareReport.Generator.ps1
index a97a29906..fb974d7ef 100644
--- a/images/macos/software-report/SoftwareReport.Generator.ps1
+++ b/images/macos/software-report/SoftwareReport.Generator.ps1
@@ -141,12 +141,17 @@ if ($os.IsLessThanMonterey) {
 
 if ($os.IsCatalina) {
     $utilitiesList += @(
-        (Get-VirtualBoxVersion),
         (Get-VagrantVersion),
         (Get-ParallelVersion)
     )
 }
 
+if (-not $os.IsBigSur) {
+    $utilitiesList += @(
+        (Get-VirtualBoxVersion)
+    )
+}
+
 $markdown += New-MDList -Style Unordered -Lines ($utilitiesList | Sort-Object)
 
 # Tools
diff --git a/images/macos/templates/macOS-12.json b/images/macos/templates/macOS-12.json
index 19cacb0e4..e4b980b08 100644
--- a/images/macos/templates/macOS-12.json
+++ b/images/macos/templates/macOS-12.json
@@ -152,10 +152,12 @@
                 "./provision/core/ruby.sh",
                 "./provision/core/rubygem.sh",
                 "./provision/core/git.sh",
-                "./provision/core/node.sh"
+                "./provision/core/node.sh",
+                "./provision/core/commonutils.sh"
             ],
             "environment_vars": [
-                "API_PAT={{user `github_api_pat`}}"
+                "API_PAT={{user `github_api_pat`}}",
+                "USER_PASSWORD={{user `vm_password`}}"
             ]
         },
         {
@@ -177,7 +179,6 @@
             "type": "shell",
             "execute_command": "chmod +x {{ .Path }}; {{ .Vars }} {{ .Path }}",
             "scripts": [
-                "./provision/core/commonutils.sh",
                 "./provision/core/llvm.sh",
                 "./provision/core/golang.sh",
                 "./provision/core/swiftlint.sh",
diff --git a/images/macos/tests/BasicTools.Tests.ps1 b/images/macos/tests/BasicTools.Tests.ps1
index 21f6de5e0..8bfa45aea 100644
--- a/images/macos/tests/BasicTools.Tests.ps1
+++ b/images/macos/tests/BasicTools.Tests.ps1
@@ -144,7 +144,7 @@ Describe "vagrant" -Skip:($os.IsHigherThanCatalina) {
     }
 }
 
-Describe "virtualbox" -Skip:($os.IsHigherThanCatalina) {
+Describe "virtualbox" -Skip:($os.IsBigSur) {
     It "virtualbox" {
         "vboxmanage -v" | Should -ReturnZeroExitCode
     }
diff --git a/images/macos/tests/Common.Tests.ps1 b/images/macos/tests/Common.Tests.ps1
index 7938abfa9..88f148e05 100644
--- a/images/macos/tests/Common.Tests.ps1
+++ b/images/macos/tests/Common.Tests.ps1
@@ -120,4 +120,10 @@ Describe "GraalVM" {
     It "native-image" {
         '$GRAALVM_11_ROOT/native-image --version' | Should -ReturnZeroExitCode
     }
+}
+
+Describe "VirtualBox" -Skip:($os.IsBigSur) {
+    It "Check kext kernel modules" {
+        kextstat | Out-String | Should -Match "org.virtualbox.kext"
+    }
 }
\ No newline at end of file
diff --git a/images/macos/toolsets/toolset-12.json b/images/macos/toolsets/toolset-12.json
index b152660de..1cb3633a1 100644
--- a/images/macos/toolsets/toolset-12.json
+++ b/images/macos/toolsets/toolset-12.json
@@ -149,7 +149,8 @@
             "imagemagick"
         ],
         "cask_packages": [
-            "julia"
+            "julia",
+            "virtualbox"
         ]
     },
     "gcc": {