diff --git a/src/Aspire.Hosting.Azure/AzureResourcePreparer.cs b/src/Aspire.Hosting.Azure/AzureResourcePreparer.cs
index f2423151be8..4030996136b 100644
--- a/src/Aspire.Hosting.Azure/AzureResourcePreparer.cs
+++ b/src/Aspire.Hosting.Azure/AzureResourcePreparer.cs
@@ -380,7 +380,10 @@ private async Task<HashSet<IAzureResource>> GetAzureReferences(IResource resourc
 
         if (resource.TryGetAnnotationsOfType<CommandLineArgsCallbackAnnotation>(out var commandLineArgsCallbackAnnotations))
         {
-            var context = new CommandLineArgsCallbackContext([], resource, cancellationToken: cancellationToken);
+            var context = new CommandLineArgsCallbackContext([], resource, cancellationToken: cancellationToken)
+            {
+                ExecutionContext = executionContext
+            };
 
             foreach (var c in commandLineArgsCallbackAnnotations)
             {
diff --git a/src/Aspire.Hosting/ResourceBuilderExtensions.cs b/src/Aspire.Hosting/ResourceBuilderExtensions.cs
index 129c5e0e5f4..911f09ee8e5 100644
--- a/src/Aspire.Hosting/ResourceBuilderExtensions.cs
+++ b/src/Aspire.Hosting/ResourceBuilderExtensions.cs
@@ -2310,15 +2310,15 @@ public static IResourceBuilder<T> WithVSCodeDebugSupport<T>(this IResourceBuilde
         ArgumentException.ThrowIfNullOrWhiteSpace(projectPath);
         ArgumentException.ThrowIfNullOrWhiteSpace(debugAdapterId);
 
+        if (!builder.ApplicationBuilder.ExecutionContext.IsRunMode)
+        {
+            return builder;
+        }
+
         if (builder is IResourceBuilder<IResourceWithArgs> resourceWithArgs)
         {
             resourceWithArgs.WithArgs(ctx =>
             {
-                if (!ctx.ExecutionContext.IsRunMode)
-                {
-                    return;
-                }
-
                 var config = ctx.ExecutionContext.ServiceProvider.GetRequiredService<IConfiguration>();
                 if (ExtensionUtils.IsExtensionHost(config) && argsCallback is not null)
                 {
diff --git a/tests/Aspire.Hosting.Azure.Tests/AzureResourcePreparerTests.cs b/tests/Aspire.Hosting.Azure.Tests/AzureResourcePreparerTests.cs
index af04b88e227..96af844a4c7 100644
--- a/tests/Aspire.Hosting.Azure.Tests/AzureResourcePreparerTests.cs
+++ b/tests/Aspire.Hosting.Azure.Tests/AzureResourcePreparerTests.cs
@@ -235,6 +235,33 @@ public async Task NullCommandLineArgIsIgnored()
         Assert.True(true);
     }
 
+    [Fact]
+    public async Task CommandLineArgsCallbackContextHasCorrectExecutionContextDuringPublish()
+    {
+        using var builder = TestDistributedApplicationBuilder.Create(DistributedApplicationOperation.Publish);
+        builder.AddAzureContainerAppEnvironment("env");
+
+        DistributedApplicationExecutionContext? capturedExecutionContext = null;
+
+        // Create a project with a WithArgs callback that captures the ExecutionContext
+        var api = builder.AddProject<Project>("api", launchProfileName: null)
+            .WithArgs(context =>
+            {
+                // Capture the ExecutionContext to verify it's set correctly
+                capturedExecutionContext = context.ExecutionContext;
+            });
+
+        using var app = builder.Build();
+        
+        // This should not throw - the ExecutionContext should be set correctly
+        await ExecuteBeforeStartHooksAsync(app, default);
+
+        // Verify the ExecutionContext was captured and is in Publish mode
+        Assert.NotNull(capturedExecutionContext);
+        Assert.True(capturedExecutionContext.IsPublishMode);
+        Assert.False(capturedExecutionContext.IsRunMode);
+    }
+
     private sealed class Project : IProjectMetadata
     {
         public string ProjectPath => "project";
diff --git a/tests/Aspire.Hosting.Tests/ExecutableResourceBuilderExtensionTests.cs b/tests/Aspire.Hosting.Tests/ExecutableResourceBuilderExtensionTests.cs
index 2d8818f1277..db6a2f60bb6 100644
--- a/tests/Aspire.Hosting.Tests/ExecutableResourceBuilderExtensionTests.cs
+++ b/tests/Aspire.Hosting.Tests/ExecutableResourceBuilderExtensionTests.cs
@@ -1,5 +1,10 @@
 // Licensed to the .NET Foundation under one or more agreements.
 // The .NET Foundation licenses this file to you under the MIT license.
+
+#pragma warning disable ASPIREEXTENSION001 // Type is for evaluation purposes only and is subject to change or removal in future updates. Suppress this diagnostic to proceed.
+#pragma warning disable IDE0005 // Using directive is unnecessary.
+
+using Aspire.Hosting.ApplicationModel;
 using Aspire.Hosting.Utils;
 
 namespace Aspire.Hosting.Tests;
@@ -65,4 +70,29 @@ public void WithWorkingDirectoryAllowsEmptyString()
         var annotation = executable.Resource.Annotations.OfType<ExecutableAnnotation>().Single();
         Assert.Equal(builder.AppHostDirectory, annotation.WorkingDirectory);
     }
+
+    [Fact]
+    public void WithVSCodeDebugSupportAddsAnnotationInRunMode()
+    {
+        using var builder = TestDistributedApplicationBuilder.Create(DistributedApplicationOperation.Run);
+        var executable = builder.AddExecutable("myexe", "command", "workingdirectory")
+            .WithVSCodeDebugSupport("project.py", "python", "ms-python.python");
+
+        var annotation = executable.Resource.Annotations.OfType<SupportsDebuggingAnnotation>().SingleOrDefault();
+        Assert.NotNull(annotation);
+        Assert.Equal("project.py", annotation.ProjectPath);
+        Assert.Equal("python", annotation.DebugAdapterId);
+        Assert.Equal("ms-python.python", annotation.RequiredExtensionId);
+    }
+
+    [Fact]
+    public void WithVSCodeDebugSupportDoesNotAddAnnotationInPublishMode()
+    {
+        using var builder = TestDistributedApplicationBuilder.Create(DistributedApplicationOperation.Publish);
+        var executable = builder.AddExecutable("myexe", "command", "workingdirectory")
+            .WithVSCodeDebugSupport("project.py", "python", "ms-python.python");
+
+        var annotation = executable.Resource.Annotations.OfType<SupportsDebuggingAnnotation>().SingleOrDefault();
+        Assert.Null(annotation);
+    }
 }
\ No newline at end of file