diff --git a/images/macos/helpers/Common.Helpers.psm1 b/images/macos/helpers/Common.Helpers.psm1
index f77a8c2b..90981790 100644
--- a/images/macos/helpers/Common.Helpers.psm1
+++ b/images/macos/helpers/Common.Helpers.psm1
@@ -27,16 +27,17 @@ function Get-EnvironmentVariable($variable) {
 # It can be used for OS-specific tests
 function Get-OSVersion {
     $osVersion = [Environment]::OSVersion
+    $osVersionMajorMinor = $osVersion.Version.ToString(2)
     return [PSCustomObject]@{
         Version = $osVersion.Version
         Platform = $osVersion.Platform
-        IsHighSierra = $osVersion.Version.Major -eq 17
-        IsMojave = $osVersion.Version.Major -eq 18
-        IsCatalina = $osVersion.Version.Major -eq 19
-        IsBigSur = $osVersion.Version.Major -eq 20
-        IsLessThanCatalina = $osVersion.Version.Major -lt 19
-        IsLessThanBigSur = $osVersion.Version.Major -lt 20
-        IsHigherThanMojave = $osVersion.Version.Major -gt 18
+        IsHighSierra = $osVersionMajorMinor -eq "10.13"
+        IsMojave = $osVersionMajorMinor -eq "10.14"
+        IsCatalina = $osVersionMajorMinor -eq "10.15"
+        IsBigSur = $osVersionMajorMinor -eq "11.0"
+        IsLessThanCatalina = [SemVer]$osVersion.Version -lt "10.15"
+        IsLessThanBigSur = [SemVer]$osVersion.Version -lt "11.0"
+        IsHigherThanMojave = [SemVer]$osVersion.Version -ge "10.15"
     }
 }
 
diff --git a/images/macos/toolsets/toolset-10.15.json b/images/macos/toolsets/toolset-10.15.json
index fd0ea45f..132cad5c 100644
--- a/images/macos/toolsets/toolset-10.15.json
+++ b/images/macos/toolsets/toolset-10.15.json
@@ -11,16 +11,23 @@
             "6.12.0.93", "6.10.0.106", "6.8.0.123", "6.6.0.166", "6.4.0.208"
         ],
         "ios-versions": [
-            "14.2.0.12", "14.0.0.0", "13.20.2.2", "13.18.2.1", "13.16.0.13", "13.14.1.39", "13.10.0.21", "13.8.3.0", "13.6.0.12", "13.4.0.2", "13.2.0.47"
+            "14.4.1.3", "14.2.0.12", "14.0.0.0", "13.20.2.2", "13.18.2.1", "13.16.0.13", "13.14.1.39", "13.10.0.21", "13.8.3.0", "13.6.0.12", "13.4.0.2", "13.2.0.47"
         ],
         "mac-versions": [
-            "6.20.2.2", "6.18.3.2", "6.16.0.13", "6.14.1.39", "6.10.0.21", "6.8.3.0", "6.6.0.12", "6.4.0.2", "6.2.0.47"
+            "6.22.1.26", "6.20.2.2", "6.18.3.2", "6.16.0.13", "6.14.1.39", "6.10.0.21", "6.8.3.0", "6.6.0.12", "6.4.0.2", "6.2.0.47"
         ],
         "android-versions": [
-            "11.0.2.0", "10.3.1.4", "10.2.0.100", "10.1.3.7", "10.0.6.2"
+            "11.1.0.17", "11.0.2.0", "10.3.1.4", "10.2.0.100", "10.1.3.7", "10.0.6.2"
         ],
         "bundle-default": "6_12_1",
         "bundles": [
+            {
+                "symlink": "6_12_3",
+                "mono":"6.12",
+                "ios": "14.4",
+                "mac": "6.22",
+                "android": "11.1"
+            },
             {
                 "symlink": "6_12_2",
                 "mono":"6.12",
diff --git a/images/macos/toolsets/toolset-11.0.json b/images/macos/toolsets/toolset-11.0.json
index 02df773b..75dcf1ed 100644
--- a/images/macos/toolsets/toolset-11.0.json
+++ b/images/macos/toolsets/toolset-11.0.json
@@ -11,16 +11,23 @@
             "6.12.0.93"
         ],
         "ios-versions": [
-            "14.2.0.12", "14.0.0.0", "13.20.2.2"
+            "14.4.1.3", "14.2.0.12", "14.0.0.0", "13.20.2.2"
         ],
         "mac-versions": [
-            "6.20.2.2"
+            "6.22.1.26", "6.20.2.2"
         ],
         "android-versions": [
-            "11.0.2.0"
+            "11.1.0.17", "11.0.2.0"
         ],
         "bundle-default": "6_12_0",
         "bundles": [
+            {
+                "symlink": "6_12_3",
+                "mono":"6.12",
+                "ios": "14.4",
+                "mac": "6.22",
+                "android": "11.1"
+            },
             {
                 "symlink": "6_12_2",
                 "mono":"6.12",