diff --git a/supervisor/shared/web_workflow/websocket.c b/supervisor/shared/web_workflow/websocket.c
index ef3015a8b7..4b9e4796cd 100644
--- a/supervisor/shared/web_workflow/websocket.c
+++ b/supervisor/shared/web_workflow/websocket.c
@@ -78,7 +78,7 @@ void websocket_handoff(socketpool_socket_obj_t *socket) {
 }
 
 bool websocket_connected(void) {
-    return !cp_serial.closed && common_hal_socketpool_socket_get_connected(&cp_serial.socket);
+    return _incoming_ringbuf.size > 0 && !cp_serial.closed && common_hal_socketpool_socket_get_connected(&cp_serial.socket);
 }
 
 static bool _read_byte(uint8_t *c) {
diff --git a/supervisor/shared/workflow.c b/supervisor/shared/workflow.c
index a3fd287bb0..f3bc99cb5e 100644
--- a/supervisor/shared/workflow.c
+++ b/supervisor/shared/workflow.c
@@ -48,6 +48,8 @@
 #endif
 static background_callback_t workflow_background_cb;
 
+static bool workflow_started = false;
+
 static void workflow_background(void *data) {
     #if CIRCUITPY_WEB_WORKFLOW
     supervisor_web_workflow_background();
@@ -70,6 +72,9 @@ void supervisor_workflow_reset(void) {
 }
 
 void supervisor_workflow_request_background(void) {
+    if (!workflow_started) {
+        return;
+    }
     background_callback_add_core(&workflow_background_cb);
 }
 
@@ -116,6 +121,8 @@ void supervisor_workflow_start(void) {
     #if CIRCUITPY_WEB_WORKFLOW
     supervisor_start_web_workflow();
     #endif
+
+    workflow_started = true;
 }
 
 FRESULT supervisor_workflow_mkdir_parents(FATFS *fs, char *path) {