diff --git a/src/CommunityToolkit.Aspire.Hosting.Dapr/DaprDistributedApplicationLifecycleHook.cs b/src/CommunityToolkit.Aspire.Hosting.Dapr/DaprDistributedApplicationLifecycleHook.cs
index 09df82683..4b3649423 100644
--- a/src/CommunityToolkit.Aspire.Hosting.Dapr/DaprDistributedApplicationLifecycleHook.cs
+++ b/src/CommunityToolkit.Aspire.Hosting.Dapr/DaprDistributedApplicationLifecycleHook.cs
@@ -61,7 +61,15 @@ private async Task OnBeforeStartAsync(BeforeStartEvent @event, CancellationToken
 
             var daprSidecar = daprAnnotation.Sidecar;
 
-
+            // Propagate WaitAnnotations from the original resource to the Dapr sidecar
+            if (resource.TryGetAnnotationsOfType<WaitAnnotation>(out var waitAnnotations))
+            {
+                foreach (var waitAnnotation in waitAnnotations)
+                {
+                    daprSidecar.Annotations.Add(waitAnnotation);
+                }
+            }
+            
             var sidecarOptionsAnnotation = daprSidecar.Annotations.OfType<DaprSidecarOptionsAnnotation>().LastOrDefault();
 
             var sidecarOptions = sidecarOptionsAnnotation?.Options;
@@ -205,6 +213,15 @@ private async Task OnBeforeStartAsync(BeforeStartEvent @event, CancellationToken
             var daprCliResourceName = $"{daprSidecar.Name}-cli";
             var daprCli = new ExecutableResource(daprCliResourceName, fileName, appHostDirectory);
 
+            // Propagate WaitAnnotations from the original resource to the Dapr CLI executable
+            if (resource.TryGetAnnotationsOfType<WaitAnnotation>(out var resourceWaitAnnotations))
+            {
+                foreach (var waitAnnotation in resourceWaitAnnotations)
+                {
+                    daprCli.Annotations.Add(waitAnnotation);
+                }
+            }
+
             // Make the Dapr CLI wait for the component resources it references
             foreach (var componentRef in componentReferenceAnnotations)
             {
diff --git a/tests/CommunityToolkit.Aspire.Hosting.Dapr.Tests/WithDaprSidecarTests.cs b/tests/CommunityToolkit.Aspire.Hosting.Dapr.Tests/WithDaprSidecarTests.cs
index e7129ba01..5d3b39a59 100644
--- a/tests/CommunityToolkit.Aspire.Hosting.Dapr.Tests/WithDaprSidecarTests.cs
+++ b/tests/CommunityToolkit.Aspire.Hosting.Dapr.Tests/WithDaprSidecarTests.cs
@@ -2,7 +2,6 @@
 // The .NET Foundation licenses this file to you under the MIT license.
 
 using Aspire.Hosting;
-using Aspire.Hosting.ApplicationModel;
 
 namespace CommunityToolkit.Aspire.Hosting.Dapr.Tests;
 
@@ -111,4 +110,72 @@ public void DaprSidecarCanReferenceComponents()
         Assert.Contains(referenceAnnotations, a => a.Component.Name == "statestore");
         Assert.Contains(referenceAnnotations, a => a.Component.Name == "pubsub");
     }
+
+    [Fact]
+    public void ResourceWithDaprSidecarAndNoWaitAnnotations_CreatesBasicSidecar()
+    {
+        var builder = DistributedApplication.CreateBuilder();
+
+        var app = builder.AddProject<Projects.CommunityToolkit_Aspire_Hosting_Dapr_ServiceA>("test")
+            .WithDaprSidecar();
+
+        // Verify no wait annotations on the main resource
+        Assert.Empty(app.Resource.Annotations.OfType<WaitAnnotation>());
+
+        // Verify the sidecar resource exists
+        var sidecarResource = Assert.Single(builder.Resources.OfType<DaprSidecarResource>());
+
+        // Verify the sidecar is properly linked
+        var sidecarAnnotation = Assert.Single(app.Resource.Annotations.OfType<DaprSidecarAnnotation>());
+        Assert.Equal(sidecarResource, sidecarAnnotation.Sidecar);
+    }
+    
+    [Fact]
+    public void ResourceWithWaitAnnotationAndDaprSidecar_SetsUpCorrectDependencies()
+    {
+        var builder = DistributedApplication.CreateBuilder();
+        
+        var database = builder.AddContainer("db", "postgres");
+        
+        var app = builder.AddProject<Projects.CommunityToolkit_Aspire_Hosting_Dapr_ServiceA>("test")
+            .WaitFor(database)
+            .WithDaprSidecar();
+        
+        // Verify the main resource has the wait annotation
+        var waitAnnotation = Assert.Single(app.Resource.Annotations.OfType<WaitAnnotation>());
+        Assert.Equal("db", waitAnnotation.Resource.Name);
+        
+        // Verify the sidecar resource exists
+        var sidecarResource = Assert.Single(builder.Resources.OfType<DaprSidecarResource>());
+        Assert.NotNull(sidecarResource);
+        
+        // The actual propagation happens in the lifecycle hook, but we can verify the setup is correct
+        var sidecarAnnotation = Assert.Single(app.Resource.Annotations.OfType<DaprSidecarAnnotation>());
+        Assert.Equal(sidecarResource, sidecarAnnotation.Sidecar);
+    }
+
+    [Fact] 
+    public void ResourceWithMultipleWaitAnnotationsAndDaprSidecar_HasAllWaitDependencies()
+    {
+        var builder = DistributedApplication.CreateBuilder();
+        
+        var database = builder.AddContainer("db", "postgres");
+        var redis = builder.AddContainer("cache", "redis");
+        
+        var app = builder.AddProject<Projects.CommunityToolkit_Aspire_Hosting_Dapr_ServiceA>("test")
+            .WaitFor(database)
+            .WaitFor(redis)
+            .WithDaprSidecar();
+        
+        // Verify the main resource has both wait annotations
+        var waitAnnotations = app.Resource.Annotations.OfType<WaitAnnotation>().ToList();
+        Assert.Equal(2, waitAnnotations.Count);
+        Assert.Contains(waitAnnotations, w => w.Resource.Name == "db");
+        Assert.Contains(waitAnnotations, w => w.Resource.Name == "cache");
+        
+        // Verify the sidecar resource exists and is properly linked
+        var sidecarResource = Assert.Single(builder.Resources.OfType<DaprSidecarResource>());
+        var sidecarAnnotation = Assert.Single(app.Resource.Annotations.OfType<DaprSidecarAnnotation>());
+        Assert.Equal(sidecarResource, sidecarAnnotation.Sidecar);
+    }
 }