diff --git a/src/core/api.c b/src/core/api.c
index c755f1328e..946033db89 100644
--- a/src/core/api.c
+++ b/src/core/api.c
@@ -244,6 +244,7 @@ MsQuicConnectionShutdown(
     Oper->API_CALL.Context->CONN_SHUTDOWN.Flags = Flags;
     Oper->API_CALL.Context->CONN_SHUTDOWN.ErrorCode = ErrorCode;
     Oper->API_CALL.Context->CONN_SHUTDOWN.RegistrationShutdown = FALSE;
+    Oper->API_CALL.Context->CONN_SHUTDOWN.TransportShutdown = FALSE;
 
     //
     // Queue the operation but don't wait for the completion.
@@ -1125,12 +1126,30 @@ MsQuicStreamSend(
     } else if (QueueOper) {
         Oper = QuicOperationAlloc(Connection->Worker, QUIC_OPER_TYPE_API_CALL);
         if (Oper == NULL) {
-            Status = QUIC_STATUS_OUT_OF_MEMORY;
             QuicTraceEvent(
                 AllocFailure,
                 "Allocation of '%s' failed. (%llu bytes)",
                 "STRM_SEND operation",
                 0);
+            //
+            // We can't fail the send at this point, because we're already queued
+            // the send above. So instead, we're just going to abort the whole
+            // connection.
+            //
+            if (InterlockedCompareExchange16(
+                    (short*)&Connection->BackUpOperUsed, 1, 0) != 0) {
+                goto Exit; // It's already started the shutdown.
+            }
+            Oper = &Connection->BackUpOper;
+            Oper->FreeAfterProcess = FALSE;
+            Oper->Type = QUIC_OPER_TYPE_API_CALL;
+            Oper->API_CALL.Context = &Connection->BackupApiContext;
+            Oper->API_CALL.Context->Type = QUIC_API_TYPE_CONN_SHUTDOWN;
+            Oper->API_CALL.Context->CONN_SHUTDOWN.Flags = QUIC_CONNECTION_SHUTDOWN_FLAG_SILENT;
+            Oper->API_CALL.Context->CONN_SHUTDOWN.ErrorCode = (QUIC_VAR_INT)QUIC_STATUS_OUT_OF_MEMORY;
+            Oper->API_CALL.Context->CONN_SHUTDOWN.RegistrationShutdown = FALSE;
+            Oper->API_CALL.Context->CONN_SHUTDOWN.TransportShutdown = TRUE;
+            QuicConnQueueOper(Connection, Oper);
             goto Exit;
         }
         Oper->API_CALL.Context->Type = QUIC_API_TYPE_STRM_SEND;
diff --git a/src/core/binding.c b/src/core/binding.c
index c763d2b97a..94060043b3 100644
--- a/src/core/binding.c
+++ b/src/core/binding.c
@@ -1359,8 +1359,9 @@ QuicBindingCreateConnection(
             Oper->API_CALL.Context = &NewConnection->BackupApiContext;
             Oper->API_CALL.Context->Type = QUIC_API_TYPE_CONN_SHUTDOWN;
             Oper->API_CALL.Context->CONN_SHUTDOWN.Flags = QUIC_CONNECTION_SHUTDOWN_FLAG_SILENT;
-            Oper->API_CALL.Context->CONN_SHUTDOWN.ErrorCode = 0;
+            Oper->API_CALL.Context->CONN_SHUTDOWN.ErrorCode = (QUIC_VAR_INT)QUIC_STATUS_INTERNAL_ERROR;
             Oper->API_CALL.Context->CONN_SHUTDOWN.RegistrationShutdown = FALSE;
+            Oper->API_CALL.Context->CONN_SHUTDOWN.TransportShutdown = TRUE;
             QuicConnQueueOper(NewConnection, Oper);
         }
 #pragma warning(pop)
diff --git a/src/core/connection.c b/src/core/connection.c
index 5992ada78c..19f6c73d76 100644
--- a/src/core/connection.c
+++ b/src/core/connection.c
@@ -438,7 +438,8 @@ QuicConnShutdown(
     _In_ QUIC_CONNECTION* Connection,
     _In_ uint32_t Flags,
     _In_ QUIC_VAR_INT ErrorCode,
-    _In_ BOOLEAN ShutdownFromRegistration
+    _In_ BOOLEAN ShutdownFromRegistration,
+    _In_ BOOLEAN ShutdownFromTransport
     )
 {
     if (ShutdownFromRegistration &&
@@ -447,7 +448,8 @@ QuicConnShutdown(
         return;
     }
 
-    uint32_t CloseFlags = QUIC_CLOSE_APPLICATION;
+    uint32_t CloseFlags =
+        ShutdownFromTransport ? QUIC_CLOSE_INTERNAL : QUIC_CLOSE_APPLICATION;
     if (Flags & QUIC_CONNECTION_SHUTDOWN_FLAG_SILENT ||
         (!Connection->State.Started && QuicConnIsClient(Connection))) {
         CloseFlags |= QUIC_CLOSE_SILENT;
@@ -475,6 +477,7 @@ QuicConnUninitialize(
         Connection,
         QUIC_CONNECTION_SHUTDOWN_FLAG_SILENT,
         QUIC_ERROR_NO_ERROR,
+        FALSE,
         FALSE);
 
     //
@@ -1868,7 +1871,7 @@ QuicConnStart(
     CxPlatDispatchLockRelease(&Connection->Registration->ConnectionLock);
 
     if (RegistrationShutingDown) {
-        QuicConnShutdown(Connection, ShutdownFlags, ShutdownErrorCode, FALSE);
+        QuicConnShutdown(Connection, ShutdownFlags, ShutdownErrorCode, FALSE, FALSE);
         if (ServerName != NULL) {
             CXPLAT_FREE(ServerName, QUIC_POOL_SERVERNAME);
         }
@@ -3330,6 +3333,7 @@ QuicConnQueueRouteCompletion(
         Oper->API_CALL.Context->CONN_SHUTDOWN.Flags = QUIC_CONNECTION_SHUTDOWN_FLAG_SILENT;
         Oper->API_CALL.Context->CONN_SHUTDOWN.ErrorCode = QUIC_ERROR_INTERNAL_ERROR;
         Oper->API_CALL.Context->CONN_SHUTDOWN.RegistrationShutdown = FALSE;
+        Oper->API_CALL.Context->CONN_SHUTDOWN.TransportShutdown = TRUE;
         QuicConnQueueHighestPriorityOper(Connection, Oper);
     }
 
@@ -7312,7 +7316,8 @@ QuicConnProcessApiOperation(
             Connection,
             ApiCtx->CONN_SHUTDOWN.Flags,
             ApiCtx->CONN_SHUTDOWN.ErrorCode,
-            ApiCtx->CONN_SHUTDOWN.RegistrationShutdown);
+            ApiCtx->CONN_SHUTDOWN.RegistrationShutdown,
+            ApiCtx->CONN_SHUTDOWN.TransportShutdown);
         break;
 
     case QUIC_API_TYPE_CONN_START:
diff --git a/src/core/operation.h b/src/core/operation.h
index 8dcccce109..dde2363b70 100644
--- a/src/core/operation.h
+++ b/src/core/operation.h
@@ -97,7 +97,8 @@ typedef struct QUIC_API_CONTEXT {
         } CONN_CLOSED;
         struct {
             QUIC_CONNECTION_SHUTDOWN_FLAGS Flags;
-            BOOLEAN RegistrationShutdown;
+            BOOLEAN RegistrationShutdown : 1;
+            BOOLEAN TransportShutdown : 1;
             QUIC_VAR_INT ErrorCode;
         } CONN_SHUTDOWN;
         struct {
diff --git a/src/core/registration.c b/src/core/registration.c
index 2704e4e137..7902b9fac2 100644
--- a/src/core/registration.c
+++ b/src/core/registration.c
@@ -240,6 +240,7 @@ MsQuicRegistrationShutdown(
                 Oper->API_CALL.Context->CONN_SHUTDOWN.Flags = Flags;
                 Oper->API_CALL.Context->CONN_SHUTDOWN.ErrorCode = ErrorCode;
                 Oper->API_CALL.Context->CONN_SHUTDOWN.RegistrationShutdown = TRUE;
+                Oper->API_CALL.Context->CONN_SHUTDOWN.TransportShutdown = FALSE;
                 QuicConnQueueHighestPriorityOper(Connection, Oper);
             }
 
diff --git a/src/core/stream_send.c b/src/core/stream_send.c
index a98654f364..9fa05dbd83 100644
--- a/src/core/stream_send.c
+++ b/src/core/stream_send.c
@@ -609,7 +609,7 @@ QuicStreamSendFlush(
     if (Start) {
         (void)QuicStreamStart(
             Stream,
-            QUIC_STREAM_START_FLAG_IMMEDIATE,
+            QUIC_STREAM_START_FLAG_IMMEDIATE | QUIC_STREAM_START_FLAG_SHUTDOWN_ON_FAIL,
             FALSE);
     }