diff --git a/images/macos/provision/core/commonutils.sh b/images/macos/provision/core/commonutils.sh
index 550e1abe0832..bb4c2873520a 100644
--- a/images/macos/provision/core/commonutils.sh
+++ b/images/macos/provision/core/commonutils.sh
@@ -13,6 +13,12 @@ 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_BigSur; then
+    osascript $HOME/utils/confirm-identified-developers.scpt $USER_PASSWORD
+fi
+
 # Specify Bazel version 3.7.1 to install due to the bug with 4.0.0: https://github.com/bazelbuild/bazel/pull/12882
 if is_Less_Catalina; then
     export USE_BAZEL_VERSION="3.7.1"
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 000000000000..9c293cae3dba
--- /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 240efc0cf9aa..bc6493ec4dc2 100644
--- a/images/macos/software-report/SoftwareReport.Common.psm1
+++ b/images/macos/software-report/SoftwareReport.Common.psm1
@@ -394,7 +394,7 @@ 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 c4b82d9f70db..534bf0c5ca02 100644
--- a/images/macos/software-report/SoftwareReport.Generator.ps1
+++ b/images/macos/software-report/SoftwareReport.Generator.ps1
@@ -129,7 +129,8 @@ $utilitiesList = @(
     (Get-MongodVersion),
     (Get-7zipVersion),
     (Get-BsdtarVersion),
-    (Get-GnuTarVersion)
+    (Get-GnuTarVersion),
+    (Get-VirtualBoxVersion)
 )
 
 if ($os.IsHigherThanMojave) {
@@ -140,7 +141,6 @@ if ($os.IsHigherThanMojave) {
 
 if ($os.IsLessThanBigSur) {
     $utilitiesList += @(
-        (Get-VirtualBoxVersion),
         (Get-VagrantVersion),
         (Get-ParallelVersion)
     )
diff --git a/images/macos/templates/macOS-11.json b/images/macos/templates/macOS-11.json
index cf8bcbc9812d..6e3480c435f7 100644
--- a/images/macos/templates/macOS-11.json
+++ b/images/macos/templates/macOS-11.json
@@ -142,7 +142,11 @@
                 "./provision/core/ruby.sh",
                 "./provision/core/rubygem.sh",
                 "./provision/core/git.sh",
-                "./provision/core/node.sh"
+                "./provision/core/node.sh",
+                "./provision/core/commonutils.sh"
+            ],
+            "environment_vars": [
+                "USER_PASSWORD={{user `vm_password`}}"
             ]
         },
         {
@@ -164,7 +168,6 @@
             "type": "shell",
             "execute_command": "chmod +x {{ .Path }}; {{ .Vars }} {{ .Path }}",
             "scripts": [
-                "./provision/core/commonutils.sh",
                 "./provision/core/swiftlint.sh",
                 "./provision/core/openjdk.sh",
                 "./provision/core/php.sh",
diff --git a/images/macos/tests/BasicTools.Tests.ps1 b/images/macos/tests/BasicTools.Tests.ps1
index e5248800c938..a57c723b3056 100644
--- a/images/macos/tests/BasicTools.Tests.ps1
+++ b/images/macos/tests/BasicTools.Tests.ps1
@@ -144,8 +144,8 @@ Describe "vagrant" -Skip:($os.IsBigSur) {
     }
 }
 
-Describe "virtualbox" -Skip:($os.IsBigSur) {
-    It "virtualbox" {
+Describe "VirtualBox" {
+    It "vboxmanage" {
         "vboxmanage -v" | Should -ReturnZeroExitCode
     }
 }
diff --git a/images/macos/tests/Common.Tests.ps1 b/images/macos/tests/Common.Tests.ps1
index 0c2366a1b7f9..7b9a3b7608ca 100644
--- a/images/macos/tests/Common.Tests.ps1
+++ b/images/macos/tests/Common.Tests.ps1
@@ -97,4 +97,10 @@ Describe "Bicep" {
     It "Bicep" {
         "bicep --version" | Should -ReturnZeroExitCode
     }
+}
+
+Describe "VirtualBox" {
+    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-11.json b/images/macos/toolsets/toolset-11.json
index 0b45dd16c818..9790588697b5 100644
--- a/images/macos/toolsets/toolset-11.json
+++ b/images/macos/toolsets/toolset-11.json
@@ -155,7 +155,8 @@
             "zstd"
         ],
         "cask_packages": [
-            "julia"
+            "julia",
+            "virtualbox"
         ]
     },
     "gcc": {