diff --git a/.azure-pipelines/ultimate-pipeline.yml b/.azure-pipelines/ultimate-pipeline.yml
index 57774d4b2696..f979125f47f3 100644
--- a/.azure-pipelines/ultimate-pipeline.yml
+++ b/.azure-pipelines/ultimate-pipeline.yml
@@ -2034,9 +2034,10 @@ stages:
     - script: tracer\build.cmd BuildAspNetIntegrationTests -Framework $(framework)
       displayName: BuildWindowsIntegrationTests
 
-    - script: |
-        docker compose build --build-arg dotnet_tracer_msi=.$(relativeMsiOutputDirectory)/*.msi --build-arg ENABLE_32_BIT=$(enable32bit) IntegrationTests.IIS
-        docker compose up -d IntegrationTests.IIS
+    - powershell: |
+        mkdir -Force "./artifacts/build_data/logs/LoaderOptimizationStartup"
+        docker compose build --build-arg DOTNET_TRACER_MSI=.$(relativeMsiOutputDirectory)/*.msi --build-arg ENABLE_32_BIT=$(enable32bit) IntegrationTests.IIS.LoaderOptimizationStartup
+        docker compose up -d IntegrationTests.IIS.LoaderOptimizationStartup
       displayName: docker-compose start IntegrationTests.IIS
       retryCountOnTaskFailure: 5
       env:
diff --git a/docker-compose.yml b/docker-compose.yml
index be0e1399d555..36dcc41a9a1e 100644
--- a/docker-compose.yml
+++ b/docker-compose.yml
@@ -340,14 +340,16 @@ services:
 
   # The IIS images are based on Windows images, so they can only be run on Docker for Windows,
   # and only after switching to run Windows containers
-  IntegrationTests.IIS:
+  IntegrationTests.IIS.LoaderOptimizationStartup:
     build:
       context: ./
       args:
         - ENABLE_32_BIT
         - DOTNET_TRACER_MSI
-      dockerfile: ./tracer/build/_build/docker/iis.dockerfile
+      dockerfile: ./tracer/build/_build/docker/iis.loaderoptimization.dockerfile
     image: datadog-iis-loaderoptimizationregkey
+    volumes:
+    - ./artifacts/build_data/logs/LoaderOptimizationStartup:c:/ProgramData/Datadog .NET Tracer/logs
     ports:
     - "8080:80"
     environment:
diff --git a/tracer/build/_build/docker/iis.dockerfile b/tracer/build/_build/docker/iis.loaderoptimization.dockerfile
similarity index 100%
rename from tracer/build/_build/docker/iis.dockerfile
rename to tracer/build/_build/docker/iis.loaderoptimization.dockerfile
diff --git a/tracer/test/Datadog.Trace.ClrProfiler.IntegrationTests/IIS/LoaderOptimizationStartup.cs b/tracer/test/Datadog.Trace.ClrProfiler.IntegrationTests/IIS/LoaderOptimizationStartup.cs
index 3a72e8069ba7..00f015887724 100644
--- a/tracer/test/Datadog.Trace.ClrProfiler.IntegrationTests/IIS/LoaderOptimizationStartup.cs
+++ b/tracer/test/Datadog.Trace.ClrProfiler.IntegrationTests/IIS/LoaderOptimizationStartup.cs
@@ -4,10 +4,14 @@
 // </copyright>
 
 #if NETFRAMEWORK
+using System.IO;
 using System.Net;
 using System.Net.Http;
 using System.Threading;
 using System.Threading.Tasks;
+using Datadog.Trace.Configuration.Telemetry;
+using Datadog.Trace.Logging;
+using FluentAssertions;
 using Xunit;
 using Xunit.Abstractions;
 
@@ -60,6 +64,14 @@ public async Task ApplicationDoesNotReturnErrors()
             // Server is ready to receive requests
             var responseMessage = await client.GetAsync(Url);
             Assert.Equal(HttpStatusCode.OK, responseMessage.StatusCode);
+
+            // verify we have some logs, so we know instrumentation happened
+            var logDirectory = Path.Combine(
+                DatadogLoggingFactory.GetLogDirectory(NullConfigurationTelemetry.Instance),
+                nameof(LoaderOptimizationStartup));
+
+            Output.WriteLine($"Reading files from {logDirectory}");
+            Directory.GetFiles(logDirectory).Should().NotBeEmpty();
         }
     }
 }