diff --git a/images/macos/helpers/Xcode.Helpers.psm1 b/images/macos/helpers/Xcode.Helpers.psm1
index 46e5330c1..e6411ce0c 100644
--- a/images/macos/helpers/Xcode.Helpers.psm1
+++ b/images/macos/helpers/Xcode.Helpers.psm1
@@ -151,4 +151,158 @@ function Invoke-XCVersion {
     if ($result.ExitCode -ne 0) {
         throw "Command [$Command] has finished with non-zero exit code."
     } 
+}
+
+function Get-BrokenXcodeSimulatorsList {
+    return @(
+        # tvOS Simulators
+        @{
+            SimulatorName = "Apple TV 4K (at 1080p) (2nd generation)"
+            DeviceId = "com.apple.CoreSimulator.SimDeviceType.Apple-TV-4K-2nd-generation-1080p";
+            RuntimeId = "com.apple.CoreSimulator.SimRuntime.tvOS-15-0";
+            XcodeVersion = "13.1"
+        },
+        @{
+            SimulatorName = "Apple TV 4K (at 1080p) (2nd generation)"
+            DeviceId = "com.apple.CoreSimulator.SimDeviceType.Apple-TV-4K-2nd-generation-1080p";
+            RuntimeId = "com.apple.CoreSimulator.SimRuntime.tvOS-15-2";
+            XcodeVersion = "13.2.1"
+        },
+        @{
+            SimulatorName = "Apple TV 4K (at 1080p) (2nd generation)"
+            DeviceId = "com.apple.CoreSimulator.SimDeviceType.Apple-TV-4K-2nd-generation-1080p";
+            RuntimeId = "com.apple.CoreSimulator.SimRuntime.tvOS-15-4";
+            XcodeVersion = "13.4.1"
+        },
+        @{
+            SimulatorName = "Apple TV 4K (at 1080p) (2nd generation)"
+            DeviceId = "com.apple.CoreSimulator.SimDeviceType.Apple-TV-4K-2nd-generation-1080p";
+            RuntimeId = "com.apple.CoreSimulator.SimRuntime.tvOS-16-0";
+            XcodeVersion = "14.2"
+        },
+        # watchOS-8-0 Simulators
+        @{
+            SimulatorName = "Apple Watch Series 5 - 40mm"
+            DeviceId = "com.apple.CoreSimulator.SimDeviceType.Apple-Watch-Series-5-40mm";
+            RuntimeId = "com.apple.CoreSimulator.SimRuntime.watchOS-8-0";
+            XcodeVersion = "13.1"
+        },
+        @{
+            SimulatorName = "Apple Watch Series 5 - 44mm"
+            DeviceId = "com.apple.CoreSimulator.SimDeviceType.Apple-Watch-Series-5-44mm";
+            RuntimeId = "com.apple.CoreSimulator.SimRuntime.watchOS-8-0";
+            XcodeVersion = "13.1"
+        },
+        @{
+            SimulatorName = "Apple Watch Series 6 - 40mm"
+            DeviceId = "com.apple.CoreSimulator.SimDeviceType.Apple-Watch-Series-6-40mm";
+            RuntimeId = "com.apple.CoreSimulator.SimRuntime.watchOS-8-0";
+            XcodeVersion = "13.1"
+        },
+        @{
+            SimulatorName = "Apple Watch Series 6 - 44mm"
+            DeviceId = "com.apple.CoreSimulator.SimDeviceType.Apple-Watch-Series-6-44mm";
+            RuntimeId = "com.apple.CoreSimulator.SimRuntime.watchOS-8-0";
+            XcodeVersion = "13.1"
+        },
+        @{
+            SimulatorName = "Apple Watch Series 7 - 41mm"
+            DeviceId = "com.apple.CoreSimulator.SimDeviceType.Apple-Watch-Series-7-41mm";
+            RuntimeId = "com.apple.CoreSimulator.SimRuntime.watchOS-8-0";
+            XcodeVersion = "13.1"
+        },
+        @{
+            SimulatorName = "Apple Watch Series 7 - 45mm"
+            DeviceId = "com.apple.CoreSimulator.SimDeviceType.Apple-Watch-Series-7-45mm";
+            RuntimeId = "com.apple.CoreSimulator.SimRuntime.watchOS-8-0";
+            XcodeVersion = "13.1"
+        },
+        # watchOS-8-3 Simulators
+        @{
+            SimulatorName = "Apple Watch Series 5 - 40mm"
+            DeviceId = "com.apple.CoreSimulator.SimDeviceType.Apple-Watch-Series-5-40mm";
+            RuntimeId = "com.apple.CoreSimulator.SimRuntime.watchOS-8-3";
+            XcodeVersion = "13.2.1"
+        },
+        @{
+            SimulatorName = "Apple Watch Series 5 - 44mm"
+            DeviceId = "com.apple.CoreSimulator.SimDeviceType.Apple-Watch-Series-5-44mm";
+            RuntimeId = "com.apple.CoreSimulator.SimRuntime.watchOS-8-3";
+            XcodeVersion = "13.2.1"
+        },
+        @{
+            SimulatorName = "Apple Watch Series 6 - 40mm"
+            DeviceId = "com.apple.CoreSimulator.SimDeviceType.Apple-Watch-Series-6-40mm";
+            RuntimeId = "com.apple.CoreSimulator.SimRuntime.watchOS-8-3";
+            XcodeVersion = "13.2.1"
+        },
+        @{
+            SimulatorName = "Apple Watch Series 6 - 44mm"
+            DeviceId = "com.apple.CoreSimulator.SimDeviceType.Apple-Watch-Series-6-44mm";
+            RuntimeId = "com.apple.CoreSimulator.SimRuntime.watchOS-8-3";
+            XcodeVersion = "13.2.1"
+        },
+        @{
+            SimulatorName = "Apple Watch Series 7 - 41mm"
+            DeviceId = "com.apple.CoreSimulator.SimDeviceType.Apple-Watch-Series-7-41mm";
+            RuntimeId = "com.apple.CoreSimulator.SimRuntime.watchOS-8-3";
+            XcodeVersion = "13.2.1"
+        },
+        @{
+            SimulatorName = "Apple Watch Series 7 - 45mm"
+            DeviceId = "com.apple.CoreSimulator.SimDeviceType.Apple-Watch-Series-7-45mm";
+            RuntimeId = "com.apple.CoreSimulator.SimRuntime.watchOS-8-3";
+            XcodeVersion = "13.2.1"
+        },
+        # watchOS-8-5 Simulators
+        @{
+            SimulatorName = "Apple Watch Series 5 - 40mm"
+            DeviceId = "com.apple.CoreSimulator.SimDeviceType.Apple-Watch-Series-5-40mm";
+            RuntimeId = "com.apple.CoreSimulator.SimRuntime.watchOS-8-5";
+            XcodeVersion = "13.4.1"
+        },
+        @{
+            SimulatorName = "Apple Watch Series 5 - 44mm"
+            DeviceId = "com.apple.CoreSimulator.SimDeviceType.Apple-Watch-Series-5-44mm";
+            RuntimeId = "com.apple.CoreSimulator.SimRuntime.watchOS-8-5";
+            XcodeVersion = "13.4.1"
+        },
+        @{
+            SimulatorName = "Apple Watch Series 6 - 40mm"
+            DeviceId = "com.apple.CoreSimulator.SimDeviceType.Apple-Watch-Series-6-40mm";
+            RuntimeId = "com.apple.CoreSimulator.SimRuntime.watchOS-8-5";
+            XcodeVersion = "13.4.1"
+        },
+        @{
+            SimulatorName = "Apple Watch Series 6 - 44mm"
+            DeviceId = "com.apple.CoreSimulator.SimDeviceType.Apple-Watch-Series-6-44mm";
+            RuntimeId = "com.apple.CoreSimulator.SimRuntime.watchOS-8-5";
+            XcodeVersion = "13.4.1"
+        },
+        @{
+            SimulatorName = "Apple Watch Series 7 - 41mm"
+            DeviceId = "com.apple.CoreSimulator.SimDeviceType.Apple-Watch-Series-7-41mm";
+            RuntimeId = "com.apple.CoreSimulator.SimRuntime.watchOS-8-5";
+            XcodeVersion = "13.4.1"
+        },
+        @{
+            SimulatorName = "Apple Watch Series 7 - 45mm"
+            DeviceId = "com.apple.CoreSimulator.SimDeviceType.Apple-Watch-Series-7-45mm";
+            RuntimeId = "com.apple.CoreSimulator.SimRuntime.watchOS-8-5";
+            XcodeVersion = "13.4.1"
+        },
+        # watchOS-9-0 Simulators
+        @{
+            SimulatorName = "Apple Watch SE (40mm) (2nd generation)"
+            DeviceId = "com.apple.CoreSimulator.SimDeviceType.Apple-Watch-SE-40mm-2nd-generation";
+            RuntimeId = "com.apple.CoreSimulator.SimRuntime.watchOS-9-0";
+            XcodeVersion = "14.2"
+        },
+        @{
+            SimulatorName = "Apple Watch SE (44mm) (2nd generation)"
+            DeviceId = "com.apple.CoreSimulator.SimDeviceType.Apple-Watch-SE-44mm-2nd-generation";
+            RuntimeId = "com.apple.CoreSimulator.SimRuntime.watchOS-9-0";
+            XcodeVersion = "14.2"
+        }
+    )
 }
\ No newline at end of file
diff --git a/images/macos/helpers/Xcode.Installer.psm1 b/images/macos/helpers/Xcode.Installer.psm1
index a08ee3b56..5f1812e75 100644
--- a/images/macos/helpers/Xcode.Installer.psm1
+++ b/images/macos/helpers/Xcode.Installer.psm1
@@ -160,6 +160,22 @@ function Invoke-XcodeRunFirstLaunch {
     Invoke-ValidateCommand "sudo $xcodeRootPath -runFirstLaunch"
 }
 
+function Install-AdditionalSimulatorRuntimes {
+    param(
+        [Parameter(Mandatory)]
+        [string]$Version
+    )
+
+    if (-not $Version.StartsWith("14.")) {
+        # Additional simulator runtimes are included by default for Xcode < 14
+        return
+    }
+
+    Write-Host "Installing Simulator Runtimes for Xcode $($_.link) ..."
+    $xcodebuildPath = Get-XcodeToolPath -Version $Version -ToolName "xcodebuild"
+    Invoke-ValidateCommand "$xcodebuildPath -downloadAllPlatforms"
+}
+
 function Build-XcodeSymlinks {
     param(
         [Parameter(Mandatory)]
diff --git a/images/macos/provision/core/fix-xcode-simulators.ps1 b/images/macos/provision/core/fix-xcode-simulators.ps1
new file mode 100644
index 000000000..98b1061e0
--- /dev/null
+++ b/images/macos/provision/core/fix-xcode-simulators.ps1
@@ -0,0 +1,51 @@
+$ErrorActionPreference = "Stop"
+
+Import-Module "$env:HOME/image-generation/helpers/Xcode.Helpers.psm1" -DisableNameChecking
+Import-Module "$env:HOME/image-generation/software-report/SoftwareReport.Xcode.psm1" -DisableNameChecking
+
+function Ensure-SimulatorInstalled {
+    param(
+        [Parameter(Mandatory)]
+        [string]$RuntimeId,
+        [Parameter(Mandatory)]
+        [string]$DeviceId,
+        [Parameter(Mandatory)]
+        [string]$SimulatorName,
+        [Parameter(Mandatory)]
+        [string]$XcodeVersion
+    )
+
+    $simctlPath = Get-XcodeToolPath -Version $XcodeVersion -ToolName "simctl"
+    if (-not (Test-Path $simctlPath)) {
+        Write-Host "Skip validating simulator '$SimulatorName [$RuntimeId]' because Xcode $XcodeVersion is not installed"
+        return
+    }
+
+    $simulatorFullNameDebug = "$SimulatorName [$RuntimeId]"
+    Write-Host "Checking Xcode simulator '$simulatorFullNameDebug' (Xcode $XcodeVersion)..."
+
+    # Get all available devices
+    [string]$rawDevicesInfo = Invoke-Expression "$simctlPath list devices --json"
+    $jsonDevicesInfo = ($rawDevicesInfo | ConvertFrom-Json).devices
+
+    # Checking if simulator already exists
+    $existingSimulator = $jsonDevicesInfo.$RuntimeId | Where-Object { $_.deviceTypeIdentifier -eq  $DeviceId } | Select-Object -First 1
+
+    if ($null -eq $existingSimulator) {
+        Write-Host "Simulator '$simulatorFullNameDebug' is missed. Creating it..."
+        Invoke-Expression "$simctlPath create '$SimulatorName' '$DeviceId' '$RuntimeId'"
+    } elseif ($existingSimulator.name -ne $SimulatorName) {
+        Write-Host "Simulator '$simulatorFullNameDebug' is named incorrectly. Renaming it from '$($existingSimulator.name)' to '$SimulatorName'..."
+        Invoke-Expression "$simctlPath rename '$($existingSimulator.udid)' '$SimulatorName'"
+    } else {
+        Write-Host "Simulator '$simulatorFullNameDebug' is installed correctly."
+    }
+}
+
+# First run doesn't provide full data about devices
+Get-XcodeInfoList | Out-Null
+
+Write-Host "Validating and fixing Xcode simulators..."
+Get-BrokenXcodeSimulatorsList | ForEach-Object {
+    Ensure-SimulatorInstalled -RuntimeId $_.RuntimeId -DeviceId $_.DeviceId -SimulatorName $_.SimulatorName -XcodeVersion $_.XcodeVersion
+}
\ No newline at end of file
diff --git a/images/macos/provision/core/xcode.ps1 b/images/macos/provision/core/xcode.ps1
index 2b0a709dc..d3175f387 100644
--- a/images/macos/provision/core/xcode.ps1
+++ b/images/macos/provision/core/xcode.ps1
@@ -33,8 +33,12 @@ $xcodeVersions | ForEach-Object -ThrottleLimit $threadCount -Parallel {
 
 Write-Host "Configuring Xcode versions..."
 $xcodeVersions | ForEach-Object {
+    Write-Host "Configuring Xcode $($_.link) ..."
+
     Invoke-XcodeRunFirstLaunch -Version $_.link
+    Install-AdditionalSimulatorRuntimes -Version $_.link
 }
+
 Invoke-XcodeRunFirstLaunch -Version $defaultXcode
 
 Write-Host "Configuring Xcode symlinks..."
@@ -47,16 +51,6 @@ $xcodeVersions | ForEach-Object {
     }
 }
 
-$xcodeVersions | ForEach-Object {
-    if ($_.link.StartsWith("14.")) {
-        Write-Host "Installing Simulator Runtimes..."
-
-        # tvOS and watchOS simulators are not included by default
-        $xcodebuildPath = Get-XcodeToolPath -Version $_.link -ToolName "xcodebuild"
-        Invoke-ValidateCommand "$xcodebuildPath -downloadAllPlatforms"
-    }
-}
-
 Write-Host "Rebuilding Launch Services database ..."
 $xcodeVersions | ForEach-Object {
     Rebuild-XcodeLaunchServicesDb -Version $_.link
diff --git a/images/macos/software-report/SoftwareReport.Xcode.psm1 b/images/macos/software-report/SoftwareReport.Xcode.psm1
index f1ae3e74c..f3032df51 100644
--- a/images/macos/software-report/SoftwareReport.Xcode.psm1
+++ b/images/macos/software-report/SoftwareReport.Xcode.psm1
@@ -171,8 +171,6 @@ function Format-XcodeSimulatorName {
     )
 
     $formattedDeviceName = $Device.Replace("ʀ", "R")
-    # Convert "Apple Watch Series 5 (44mm)" -> "Apple Watch Series 5 - 44mm" to make all Xcode versions consistent
-    $formattedDeviceName = $formattedDeviceName -replace '\((\d+mm)\)', '- $1'
     return $formattedDeviceName
 }
 
diff --git a/images/macos/templates/macOS-12.json b/images/macos/templates/macOS-12.json
index 0ca2661aa..52954340a 100644
--- a/images/macos/templates/macOS-12.json
+++ b/images/macos/templates/macOS-12.json
@@ -235,6 +235,11 @@
                 "./provision/core/delete-duplicate-sims.rb"
             ]
         },
+        {
+            "type": "shell",
+            "execute_command": "chmod +x {{ .Path }}; {{ .Vars }} pwsh -f {{ .Path }}",
+            "script": "./provision/core/fix-xcode-simulators.ps1"
+        },
         {
             "type": "shell",
             "inline": [
diff --git a/images/macos/tests/Xcode.Tests.ps1 b/images/macos/tests/Xcode.Tests.ps1
index 411eb041e..8c5973e08 100644
--- a/images/macos/tests/Xcode.Tests.ps1
+++ b/images/macos/tests/Xcode.Tests.ps1
@@ -111,4 +111,21 @@ Describe "Xcode simulators" {
         $defaultXcode = Get-ToolsetValue "xcode.default"
         Switch-Xcode -Version $defaultXcode
     }
+}
+
+Describe "Xcode Simulators Naming" -Skip:(-not $os.IsMonterey) {
+    $testCases = Get-BrokenXcodeSimulatorsList
+    It "Simulator '<SimulatorName> [<RuntimeId>]'" -TestCases $testCases {
+        $simctlPath = Get-XcodeToolPath -Version $XcodeVersion -ToolName "simctl"
+        [string]$rawDevicesInfo = Invoke-Expression "$simctlPath list devices --json"
+        $jsonDevicesInfo = ($rawDevicesInfo | ConvertFrom-Json).devices
+
+        $foundSimulators = $jsonDevicesInfo.$RuntimeId | Where-Object { $_.deviceTypeIdentifier -eq $DeviceId }
+        $foundSimulators | Should -HaveCount 1
+        $foundSimulators[0].name | Should -Be $SimulatorName
+
+        $foundSimulators = $jsonDevicesInfo.$RuntimeId | Where-Object { $_.name -eq $SimulatorName }
+        $foundSimulators | Should -HaveCount 1
+        $foundSimulators[0].deviceTypeIdentifier | Should -Be $DeviceId
+    }
 }
\ No newline at end of file
diff --git a/images/macos/toolsets/toolset-12.json b/images/macos/toolsets/toolset-12.json
index d5d025c42..72c1ed9a1 100644
--- a/images/macos/toolsets/toolset-12.json
+++ b/images/macos/toolsets/toolset-12.json
@@ -2,8 +2,8 @@
     "xcode": {
         "default": "14.2",
         "versions": [
-            {"link": "14.2", "version": "14.2.0"},
-            { "link": "14.1", "version": "14.1.0"},
+            { "link": "14.2", "version": "14.2.0" },
+            { "link": "14.1", "version": "14.1.0" },
             { "link": "14.0.1", "version": "14.0.1", "symlinks": ["14.0"] },
             { "link": "13.4.1", "version": "13.4.1", "symlinks": ["13.4"] },
             { "link": "13.3.1", "version": "13.3.1", "symlinks": ["13.3"] },