diff --git a/images/macos/helpers/Xcode.Installer.psm1 b/images/macos/helpers/Xcode.Installer.psm1
index 5f1812e7..e1b5bb6e 100644
--- a/images/macos/helpers/Xcode.Installer.psm1
+++ b/images/macos/helpers/Xcode.Installer.psm1
@@ -166,14 +166,14 @@ function Install-AdditionalSimulatorRuntimes {
         [string]$Version
     )
 
-    if (-not $Version.StartsWith("14.")) {
+    if ($Version.Split(".")[0] -lt 14) {
         # Additional simulator runtimes are included by default for Xcode < 14
         return
     }
 
-    Write-Host "Installing Simulator Runtimes for Xcode $($_.link) ..."
+    Write-Host "Installing Simulator Runtimes for Xcode $Version ..."
     $xcodebuildPath = Get-XcodeToolPath -Version $Version -ToolName "xcodebuild"
-    Invoke-ValidateCommand "$xcodebuildPath -downloadAllPlatforms"
+    Invoke-ValidateCommand "$xcodebuildPath -downloadAllPlatforms | xcpretty"
 }
 
 function Build-XcodeSymlinks {
diff --git a/images/macos/provision/core/xcode.ps1 b/images/macos/provision/core/xcode.ps1
index 3c9b1036..f05f9fc0 100644
--- a/images/macos/provision/core/xcode.ps1
+++ b/images/macos/provision/core/xcode.ps1
@@ -36,11 +36,13 @@ $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
 }
 
+$latestVersion = $xcodeVersions | Sort-Object -Property link -Descending | Select-Object -First 1 -ExpandProperty link
+Write-Host "Installing simulators for version $latestVersion..."
+Install-AdditionalSimulatorRuntimes -Version $latestVersion
+
 Invoke-XcodeRunFirstLaunch -Version $defaultXcode
 
 Write-Host "Configuring Xcode symlinks..."
diff --git a/images/macos/tests/Xcode.Tests.ps1 b/images/macos/tests/Xcode.Tests.ps1
index 9abec658..2d00a42a 100644
--- a/images/macos/tests/Xcode.Tests.ps1
+++ b/images/macos/tests/Xcode.Tests.ps1
@@ -98,12 +98,16 @@ Describe "Xcode simulators" {
             It "No duplicates in devices" -TestCases $testCase {
                 Switch-Xcode -Version $XcodeVersion
                 [array]$devicesList = @(Get-XcodeDevicesList | Where-Object { $_ })
+                Write-Host "Devices for $XcodeVersion"
+                Write-Host ($devicesList -join "`n")
                 Validate-ArrayWithoutDuplicates $devicesList -Because "Found duplicate device simulators"
             }
 
             It "No duplicates in pairs" -TestCases $testCase {
                 Switch-Xcode -Version $XcodeVersion
                 [array]$pairsList = @(Get-XcodePairsList | Where-Object { $_ })
+                Write-Host "Pairs for $XcodeVersion"
+                Write-Host ($pairsList -join "`n")
                 Validate-ArrayWithoutDuplicates $pairsList -Because "Found duplicate pairs simulators"
             }
         }