diff --git a/src/Microsoft.DotNet.Helix/Sdk.Tests/Microsoft.DotNet.Helix.Sdk.Tests/CreateXHarnessAppleWorkItemsTests.cs b/src/Microsoft.DotNet.Helix/Sdk.Tests/Microsoft.DotNet.Helix.Sdk.Tests/CreateXHarnessAppleWorkItemsTests.cs
index 5ff6f153d38..1de74789d8a 100644
--- a/src/Microsoft.DotNet.Helix/Sdk.Tests/Microsoft.DotNet.Helix.Sdk.Tests/CreateXHarnessAppleWorkItemsTests.cs
+++ b/src/Microsoft.DotNet.Helix/Sdk.Tests/Microsoft.DotNet.Helix.Sdk.Tests/CreateXHarnessAppleWorkItemsTests.cs
@@ -133,6 +133,9 @@ public void ArchivePayloadIsOverwritten()
             payloadArchive.Should().NotBeNullOrEmpty();
             _fileSystem.FileExists(payloadArchive).Should().BeTrue();
             _fileSystem.RemovedFiles.Should().Contain(payloadArchive);
+
+            var command = workItem.GetMetadata("Command");
+            command.Should().Contain("--launch-timeout \"00:02:00\"");
         }
 
         [Fact]
@@ -170,7 +173,7 @@ public void AppBundleIsReused()
             _task.ConfigureServices(collection);
             _task.AppBundles = new[]
             {
-                CreateAppBundle("item-1", "ios-simulator-64_13.5", appBundlePath: "apps/System.Foo.app"),
+                CreateAppBundle("item-1", "ios-device_13.5", appBundlePath: "apps/System.Foo.app"),
                 CreateAppBundle("item-2", "ios-simulator-64_13.6", appBundlePath: "apps/System.Foo.app"),
             };
 
@@ -182,25 +185,27 @@ public void AppBundleIsReused()
             _task.WorkItems.Length.Should().Be(2);
             _fileSystem.RemovedFiles.Should().BeEmpty();
 
-            var workItem1 = _task.WorkItems.Last();
-            workItem1.GetMetadata("Identity").Should().Be("item-2");
+            var workItem1 = _task.WorkItems.First();
+            workItem1.GetMetadata("Identity").Should().Be("item-1");
 
             var payloadArchive = workItem1.GetMetadata("PayloadArchive");
             payloadArchive.Should().NotBeNullOrEmpty();
             _fileSystem.FileExists(payloadArchive).Should().BeTrue();
 
             var command = workItem1.GetMetadata("Command");
-            command.Should().Contain("--target \"ios-simulator-64_13.6\"");
+            command.Should().Contain("--target \"ios-device_13.5\"");
+            command.Should().Contain("--launch-timeout \"00:05:00\"");
 
-            var workItem2 = _task.WorkItems.First();
-            workItem2.GetMetadata("Identity").Should().Be("item-1");
+            var workItem2 = _task.WorkItems.Last();
+            workItem2.GetMetadata("Identity").Should().Be("item-2");
 
             payloadArchive = workItem2.GetMetadata("PayloadArchive");
             payloadArchive.Should().NotBeNullOrEmpty();
             _fileSystem.FileExists(payloadArchive).Should().BeTrue();
 
             command = workItem2.GetMetadata("Command");
-            command.Should().Contain("--target \"ios-simulator-64_13.5\"");
+            command.Should().Contain("--target \"ios-simulator-64_13.6\"");
+            command.Should().Contain("--launch-timeout \"00:02:00\"");
         }
 
         [Fact]
diff --git a/src/Microsoft.DotNet.Helix/Sdk/CreateXHarnessAppleWorkItems.cs b/src/Microsoft.DotNet.Helix/Sdk/CreateXHarnessAppleWorkItems.cs
index fe8c942a338..76885f426f5 100644
--- a/src/Microsoft.DotNet.Helix/Sdk/CreateXHarnessAppleWorkItems.cs
+++ b/src/Microsoft.DotNet.Helix/Sdk/CreateXHarnessAppleWorkItems.cs
@@ -1,7 +1,6 @@
 using System;
 using System.IO;
 using System.Linq;
-using System.Threading;
 using System.Threading.Tasks;
 using Microsoft.Arcade.Common;
 using Microsoft.Build.Framework;
@@ -30,7 +29,10 @@ public static class MetadataNames
         private const string EntryPointScript = "xharness-helix-job.apple.sh";
         private const string RunnerScript = "xharness-runner.apple.sh";
 
-        private static readonly TimeSpan s_defaultLaunchTimeout = TimeSpan.FromMinutes(5);
+        // We have a more aggressive timeout towards simulators which tend to slow down until installation takes 20 minutes and the machine needs a reboot
+        // For this reason, it's better to be aggressive and detect a slower machine sooner
+        private static readonly TimeSpan s_defaultSimulatorLaunchTimeout = TimeSpan.FromMinutes(2);
+        private static readonly TimeSpan s_defaultDeviceLaunchTimeout = TimeSpan.FromMinutes(5);
 
         /// <summary>
         /// An array of one or more paths to iOS/tvOS app bundles (folders ending with ".app" usually)
@@ -133,7 +135,7 @@ private async Task<ITaskItem> PrepareWorkItem(
             target = target.ToLowerInvariant();
 
             // Optional timeout for the how long it takes for the app to be installed, booted and tests start executing
-            TimeSpan launchTimeout = s_defaultLaunchTimeout;
+            TimeSpan launchTimeout = target.Contains("device") ? s_defaultDeviceLaunchTimeout : s_defaultSimulatorLaunchTimeout;
             if (appBundleItem.TryGetMetadata(MetadataNames.LaunchTimeout, out string launchTimeoutProp))
             {
                 if (!TimeSpan.TryParse(launchTimeoutProp, out launchTimeout) || launchTimeout.Ticks < 0)
diff --git a/tests/XHarness/XHarness.Apple.Simulator.Run.proj b/tests/XHarness/XHarness.Apple.Simulator.Run.proj
index c67a80201e5..54a7b58068b 100644
--- a/tests/XHarness/XHarness.Apple.Simulator.Run.proj
+++ b/tests/XHarness/XHarness.Apple.Simulator.Run.proj
@@ -23,7 +23,6 @@
         <TestTarget>ios-simulator-64</TestTarget>
         <WorkItemTimeout>00:12:00</WorkItemTimeout>
         <TestTimeout>00:08:00</TestTimeout>
-        <LaunchTimeout>00:05:00</LaunchTimeout>
         <IncludesTestRunner>false</IncludesTestRunner>
         <ExpectedExitCode>200</ExpectedExitCode>
       </XHarnessAppBundleToTest>
diff --git a/tests/XHarness/XHarness.Apple.Simulator.Test.proj b/tests/XHarness/XHarness.Apple.Simulator.Test.proj
index 49c9f339a8d..babce06d5da 100644
--- a/tests/XHarness/XHarness.Apple.Simulator.Test.proj
+++ b/tests/XHarness/XHarness.Apple.Simulator.Test.proj
@@ -23,7 +23,6 @@
         <TestTarget>ios-simulator-64</TestTarget>
         <TestTimeout>00:05:00</TestTimeout>
         <WorkItemTimeout>00:15:00</WorkItemTimeout>
-        <LaunchTimeout>00:06:00</LaunchTimeout>
       </XHarnessAppBundleToTest>
     </ItemGroup>
   </Target>