diff --git a/dlls/ws2_32/tests/sock.c b/dlls/ws2_32/tests/sock.c
index b43d7d61867..d37c25f9225 100644
--- a/dlls/ws2_32/tests/sock.c
+++ b/dlls/ws2_32/tests/sock.c
@@ -3106,6 +3106,29 @@ static test_setup tests [] =
     }
 };
 
+struct send_udp_thread_param
+{
+    int sock;
+    HANDLE start_event;
+};
+
+static DWORD WINAPI send_udp_thread( void *param )
+{
+    struct send_udp_thread_param *p = param;
+    static char buf[256];
+    unsigned int i;
+    int ret;
+
+    WaitForSingleObject( p->start_event, INFINITE );
+    for (i = 0; i < 256; ++i)
+    {
+        ret = send( p->sock, buf, sizeof(buf), 0 );
+        ok( ret == sizeof(buf), "got %d, error %u, i %u.\n", ret, WSAGetLastError(), i );
+    }
+
+    return 0;
+}
+
 static void test_UDP(void)
 {
     /* This function tests UDP sendto() and recvfrom(). UDP is unreliable, so it is
@@ -3117,6 +3140,9 @@ static void test_UDP(void)
     int ss, i, n_recv, n_sent, ret;
     struct sockaddr_in addr;
     int sock;
+    struct send_udp_thread_param udp_thread_param;
+    HANDLE thread;
+
 
     memset (buf,0,sizeof(buf));
     for ( i = NUM_UDP_PEERS - 1; i >= 0; i-- ) {
@@ -3174,6 +3200,22 @@ static void test_UDP(void)
         ok( ret == sizeof(buf), "got %d, error %u.\n", ret, WSAGetLastError() );
     }
 
+    /* Test sending packets in parallel (mostly a regression test for Wine async handling race conditions). */
+    set_blocking( sock, FALSE );
+
+    udp_thread_param.sock = sock;
+    udp_thread_param.start_event = CreateEventW( NULL, FALSE, FALSE, NULL );
+    thread = CreateThread( NULL, 0, send_udp_thread, &udp_thread_param, 0, NULL );
+    SetEvent( udp_thread_param.start_event );
+    for (i = 0; i < 256; ++i)
+    {
+        ret = send( sock, buf, sizeof(buf), 0 );
+        ok( ret == sizeof(buf), "got %d, error %u, i %u.\n", ret, WSAGetLastError(), i );
+    }
+    WaitForSingleObject( thread, INFINITE );
+    CloseHandle( thread );
+    CloseHandle( udp_thread_param.start_event );
+
     closesocket(sock);
 }
 
diff --git a/server/async.c b/server/async.c
index 9cb251df5ce..80129ac0ac3 100644
--- a/server/async.c
+++ b/server/async.c
@@ -551,6 +551,16 @@ void async_set_result( struct object *obj, unsigned int status, apc_param_t tota
     }
 }
 
+int async_queue_has_waiting_asyncs( struct async_queue *queue )
+{
+    struct async *async;
+
+    LIST_FOR_EACH_ENTRY( async, &queue->queue, struct async, queue_entry )
+        if (!async->unknown_status) return 1;
+
+    return 0;
+}
+
 /* check if an async operation is waiting to be alerted */
 int async_waiting( struct async_queue *queue )
 {
diff --git a/server/file.h b/server/file.h
index 39a833cd105..7f2d1637863 100644
--- a/server/file.h
+++ b/server/file.h
@@ -237,6 +237,7 @@ extern void set_async_pending( struct async *async );
 extern void async_set_initial_status( struct async *async, unsigned int status );
 extern void async_wake_obj( struct async *async );
 extern int async_waiting( struct async_queue *queue );
+extern int async_queue_has_waiting_asyncs( struct async_queue *queue );
 extern void async_terminate( struct async *async, unsigned int status );
 extern void async_request_complete( struct async *async, unsigned int status, data_size_t result,
                                     data_size_t out_size, void *out_data );
diff --git a/server/sock.c b/server/sock.c
index c34fd3eb5eb..a884179c604 100644
--- a/server/sock.c
+++ b/server/sock.c
@@ -3945,7 +3945,7 @@ DECL_HANDLER(send_socket)
 
     if (bind_errno) status = sock_get_ntstatus( bind_errno );
     else if (sock->wr_shutdown) status = STATUS_PIPE_DISCONNECTED;
-    else if (!async_queued( &sock->write_q ))
+    else if (!async_queue_has_waiting_asyncs( &sock->write_q ))
     {
         /* If write_q is not empty, we cannot really tell if the already queued
          * asyncs will not consume all available space; if there's no space