diff --git a/src/Persistence/MartenTests/TestHelpers/catch_up_then_restart.cs b/src/Persistence/MartenTests/TestHelpers/catch_up_then_restart.cs
index efdd28f86..910530d5d 100644
--- a/src/Persistence/MartenTests/TestHelpers/catch_up_then_restart.cs
+++ b/src/Persistence/MartenTests/TestHelpers/catch_up_then_restart.cs
@@ -70,7 +70,11 @@ public async Task with_main_store()
 
 
         var tracked = await _host.TrackActivity()
+            
+            // This new helper just resets the main Marten store
+            // Equivalent to calling IHost.ResetAllMartenDataAsync()
             .ResetAllMartenDataFirst()
+            
             .PauseThenCatchUpOnMartenDaemonActivity(CatchUpMode.AndResumeNormally)
             .InvokeMessageAndWaitAsync(new AppendLetters(id, ["AAAACCCCBDEEE", "ABCDECCC", "BBBA", "DDDAE"]));
 
diff --git a/src/Persistence/Wolverine.Marten/Publishing/MartenToWolverineOutbox.cs b/src/Persistence/Wolverine.Marten/Publishing/MartenToWolverineOutbox.cs
index 44c85d4f8..e1a2373ec 100644
--- a/src/Persistence/Wolverine.Marten/Publishing/MartenToWolverineOutbox.cs
+++ b/src/Persistence/Wolverine.Marten/Publishing/MartenToWolverineOutbox.cs
@@ -18,7 +18,11 @@ public MartenToWolverineOutbox(IServiceProvider services)
 
     public async ValueTask<IMessageBatch> CreateBatch(DocumentSessionBase session)
     {
-        var context = new MessageContext(_runtime.Value, session.TenantId);
+        var context = new MessageContext(_runtime.Value, session.TenantId)
+        {
+            MultiFlushMode = MultiFlushMode.AllowMultiples
+        };
+        
         await context.EnlistInOutboxAsync(new MartenEnvelopeTransaction(session, context));
         
         return new MartenToWolverineMessageBatch(context, session);
diff --git a/src/Testing/CoreTests/Runtime/MessageContextTests.cs b/src/Testing/CoreTests/Runtime/MessageContextTests.cs
index 0f1f8036e..f3cd021f7 100644
--- a/src/Testing/CoreTests/Runtime/MessageContextTests.cs
+++ b/src/Testing/CoreTests/Runtime/MessageContextTests.cs
@@ -8,6 +8,7 @@
 using Wolverine.Runtime;
 using Wolverine.Tracking;
 using Wolverine.Transports;
+using Wolverine.Transports.Sending;
 using Wolverine.Transports.Tcp;
 using Wolverine.Util;
 using Xunit;
@@ -39,6 +40,82 @@ public MessageContextTests()
         theEnvelope = ObjectMother.Envelope();
     }
 
+    [Fact]
+    public void default_multi_flush_mode_is_OnlyOnce()
+    {
+        theContext.MultiFlushMode.ShouldBe(MultiFlushMode.OnlyOnce);
+    }
+
+    [Fact]
+    public async Task try_to_call_flush_outgoing_twice_in_normal_mode()
+    {
+        theEnvelope.Sender = Substitute.For<ISendingAgent>();
+        
+        // Wacky, but this adds it to the MessageContext
+        await theContext.As<IEnvelopeTransaction>().PersistOutgoingAsync(theEnvelope);
+        
+        // Point is that nothing happens, no exceptions
+        await theContext.FlushOutgoingMessagesAsync();
+
+        var envelope2 = ObjectMother.Envelope();
+        envelope2.Sender = Substitute.For<ISendingAgent>();
+        
+        // Wacky, but this adds it to the MessageContext
+        await theContext.As<IEnvelopeTransaction>().PersistOutgoingAsync(envelope2);
+        await theContext.FlushOutgoingMessagesAsync();
+
+        await envelope2.Sender.DidNotReceive().StoreAndForwardAsync(envelope2);
+    }
+    
+    [Fact]
+    public async Task try_to_call_flush_outgoing_twice_in_allow_multiples_mode()
+    {
+        theContext.MultiFlushMode = MultiFlushMode.AllowMultiples;
+        
+        theEnvelope.Sender = Substitute.For<ISendingAgent>();
+        
+        // Wacky, but this adds it to the MessageContext
+        await theContext.As<IEnvelopeTransaction>().PersistOutgoingAsync(theEnvelope);
+        
+        // Point is that nothing happens, no exceptions
+        await theContext.FlushOutgoingMessagesAsync();
+
+        var envelope2 = ObjectMother.Envelope();
+        envelope2.Sender = Substitute.For<ISendingAgent>();
+        
+        // Wacky, but this adds it to the MessageContext
+        await theContext.As<IEnvelopeTransaction>().PersistOutgoingAsync(envelope2);
+        await theContext.FlushOutgoingMessagesAsync();
+
+        await envelope2.Sender.Received().StoreAndForwardAsync(envelope2);
+    }
+
+    [Fact]
+    public async Task throw_on_multiple_calls_to_flush_if_the_mode_is_assert_on_multiples()
+    {
+        theContext.MultiFlushMode = MultiFlushMode.AssertOnMultiples;
+        
+        
+        theEnvelope.Sender = Substitute.For<ISendingAgent>();
+        
+        // Wacky, but this adds it to the MessageContext
+        await theContext.As<IEnvelopeTransaction>().PersistOutgoingAsync(theEnvelope);
+        await theContext.FlushOutgoingMessagesAsync();
+        
+        // Wacky, but this adds it to the MessageContext
+        var envelope2 = ObjectMother.Envelope();
+        envelope2.Sender = Substitute.For<ISendingAgent>();
+        
+        // Wacky, but this adds it to the MessageContext
+        await theContext.As<IEnvelopeTransaction>().PersistOutgoingAsync(envelope2);
+        await Should.ThrowAsync<InvalidOperationException>(async () =>
+        {
+            await theContext.FlushOutgoingMessagesAsync();
+        });
+
+        await envelope2.Sender.DidNotReceive().StoreAndForwardAsync(envelope2);
+    }
+    
     [Fact]
     public async Task reject_side_effect_as_cascading_message()
     {
diff --git a/src/Wolverine/Runtime/MessageContext.cs b/src/Wolverine/Runtime/MessageContext.cs
index 9533210bc..3e61d52e8 100644
--- a/src/Wolverine/Runtime/MessageContext.cs
+++ b/src/Wolverine/Runtime/MessageContext.cs
@@ -12,6 +12,25 @@
 
 namespace Wolverine.Runtime;
 
+public enum MultiFlushMode
+{
+    /// <summary>
+    /// The default mode, additional calls to FlushOutgoingMessages() are ignored
+    /// </summary>
+    OnlyOnce,
+    
+    /// <summary>
+    /// Allow for multiple calls to FlushOutgoingMessages()
+    /// </summary>
+    AllowMultiples,
+    
+    /// <summary>
+    /// Throw an exception on additional calls to FlushOutgoingMessages(). Use this to troubleshoot
+    /// erroneous behavior
+    /// </summary>
+    AssertOnMultiples
+}
+
 public class MessageContext : MessageBus, IMessageContext, IHasTenantId, IEnvelopeTransaction, IEnvelopeLifecycle
 {
     private IChannelCallback? _channel;
@@ -29,6 +48,12 @@ public MessageContext(IWolverineRuntime runtime, string tenantId) : base(runtime
         TenantId = runtime.Options.Durability.TenantIdStyle.MaybeCorrectTenantId(tenantId);
     }
 
+    /// <summary>
+    /// Governs how the MessageContext will handle subsequent calls to FlushOutgoingMessages(). The
+    /// default behavior is to quietly ignore any additional calls
+    /// </summary>
+    public MultiFlushMode MultiFlushMode { get; set; } = MultiFlushMode.OnlyOnce;
+
     internal IList<Envelope> Scheduled { get; } = new List<Envelope>();
 
     private bool hasRequestedReply()
@@ -45,9 +70,22 @@ public async Task FlushOutgoingMessagesAsync()
     {
         if (_hasFlushed)
         {
-            return;
+            switch (MultiFlushMode)
+            {
+                case MultiFlushMode.OnlyOnce:
+                    return;
+                
+                case MultiFlushMode.AllowMultiples:
+                    Runtime.Logger.LogWarning("Received multiple calls to FlushOutgoingMessagesAsync() to a single MessageContext");
+                    break;
+                
+                case MultiFlushMode.AssertOnMultiples:
+                    throw new InvalidOperationException(
+                        $"This MessageContext does not allow multiple calls to {nameof(FlushOutgoingMessagesAsync)} because {nameof(MultiFlushMode)} = {MultiFlushMode}");
+            }
         }
 
+        
         await AssertAnyRequiredResponseWasGenerated();
 
         if (!Outstanding.Any())