diff --git a/CHANGELOG.md b/CHANGELOG.md
index 68b500cc5..1c1c36311 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -2,7 +2,9 @@
 
 ## (Unreleased)
 
-- Add automatic retry on gateway timeout in `GrpcDurableTaskClient.WaitForInstanceCompletionAsync` in [#412](https://github.com/microsoft/durabletask-dotnet/pull/412))
+- - Add automatic retry on gateway timeout in `GrpcDurableTaskClient.WaitForInstanceCompletionAsync` in [#412](https://github.com/microsoft/durabletask-dotnet/pull/412))
+- Add specific logging for NotFound error on worker connection by @halspang in ([#413](https://github.com/microsoft/durabletask-dotnet/pull/413))
+
 
 ## v1.10.0
 
diff --git a/src/Worker/Grpc/GrpcDurableTaskWorker.Processor.cs b/src/Worker/Grpc/GrpcDurableTaskWorker.Processor.cs
index dbc18c81b..327bb0cc1 100644
--- a/src/Worker/Grpc/GrpcDurableTaskWorker.Processor.cs
+++ b/src/Worker/Grpc/GrpcDurableTaskWorker.Processor.cs
@@ -65,6 +65,16 @@ public async Task ExecuteAsync(CancellationToken cancellation)
                     // Sidecar is down - keep retrying
                     this.Logger.SidecarUnavailable();
                 }
+                catch (RpcException ex) when (ex.StatusCode == StatusCode.NotFound)
+                {
+                    // We retry on a NotFound for several reasons:
+                    // 1. It was the existing behavior through the UnexpectedError path.
+                    // 2. A 404 can be returned for a missing task hub or authentication failure. Authentication takes
+                    //    time to propagate so we should retry instead of making the user restart the application.
+                    // 3. In some cases, a task hub can be created separately from the scheduler. If a worker is deployed
+                    //    between the scheduler and task hub, it would need to be restarted to function.
+                    this.Logger.TaskHubNotFound();
+                }
                 catch (OperationCanceledException) when (cancellation.IsCancellationRequested)
                 {
                     // Shutting down, lets exit gracefully.
diff --git a/src/Worker/Grpc/Logs.cs b/src/Worker/Grpc/Logs.cs
index 1230e26e8..240a40639 100644
--- a/src/Worker/Grpc/Logs.cs
+++ b/src/Worker/Grpc/Logs.cs
@@ -22,6 +22,9 @@ static partial class Logs
         [LoggerMessage(EventId = 4, Level = LogLevel.Information, Message = "Sidecar work-item streaming connection established.")]
         public static partial void EstablishedWorkItemConnection(this ILogger logger);
 
+        [LoggerMessage(EventId = 5, Level = LogLevel.Warning, Message = "Task hub NotFound. Will continue retrying.")]
+        public static partial void TaskHubNotFound(this ILogger logger);
+
         [LoggerMessage(EventId = 10, Level = LogLevel.Debug, Message = "{instanceId}: Received request to run orchestrator '{name}' with {oldEventCount} replay and {newEventCount} new history events.")]
         public static partial void ReceivedOrchestratorRequest(this ILogger logger, string name, string instanceId, int oldEventCount, int newEventCount);