diff --git a/CHANGELOG.md b/CHANGELOG.md
index 22438f80e..f9bf5f5ed 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -30,6 +30,7 @@
 - UL: Docs: Update Sub-GHz DoorHan programming instructions (by @li0ard)
 
 ### Fixed:
+- CLI: Fix long delay with quick connect/disconnect, qFlipper should connect faster as expected again (by @WillyJL)
 - Bad KB: Fix modifier keys with HOLD/RELEASE commands (by @WillyJL)
 - Desktop: Fix lock screen hang (#438 by @aaronjamt)
 - NFC: Fix incorrect Saflok year formula (#433 by @Eltrick)
diff --git a/applications/services/cli/cli_vcp.c b/applications/services/cli/cli_vcp.c
index f65722241..6a8afe184 100644
--- a/applications/services/cli/cli_vcp.c
+++ b/applications/services/cli/cli_vcp.c
@@ -217,7 +217,11 @@ static void cli_vcp_internal_event_happened(FuriEventLoopObject* object, void* c
         // disconnect our side of the pipe
         pipe_detach_from_event_loop(cli_vcp->own_pipe);
         pipe_free(cli_vcp->own_pipe);
-        cli_vcp->own_pipe = NULL;
+
+        // wait for shell to stop
+        cli_shell_join(cli_vcp->shell);
+        cli_shell_free(cli_vcp->shell);
+        pipe_free(cli_vcp->shell_pipe);
         break;
     }
 
@@ -226,14 +230,6 @@ static void cli_vcp_internal_event_happened(FuriEventLoopObject* object, void* c
         FURI_LOG_D(TAG, "Connected");
         cli_vcp->is_connected = true;
 
-        // wait for previous shell to stop
-        furi_check(!cli_vcp->own_pipe);
-        if(cli_vcp->shell) {
-            cli_shell_join(cli_vcp->shell);
-            cli_shell_free(cli_vcp->shell);
-            pipe_free(cli_vcp->shell_pipe);
-        }
-
         // start shell thread
         PipeSideBundle bundle = pipe_alloc(VCP_BUF_SIZE, 1);
         cli_vcp->own_pipe = bundle.alices_side;
diff --git a/lib/toolbox/cli/shell/cli_shell.c b/lib/toolbox/cli/shell/cli_shell.c
index 8663577e3..05aecc444 100644
--- a/lib/toolbox/cli/shell/cli_shell.c
+++ b/lib/toolbox/cli/shell/cli_shell.c
@@ -469,11 +469,16 @@ static int32_t cli_shell_thread(void* context) {
     cli_shell_init(shell);
     FURI_LOG_D(TAG, "Started");
 
+    if(pipe_state(shell->pipe) == PipeStateBroken) goto bail;
+
     shell->motd(shell->callback_context);
     cli_shell_line_prompt(shell->components[CliShellComponentLine]);
 
+    if(pipe_state(shell->pipe) == PipeStateBroken) goto bail;
+
     furi_event_loop_run(shell->event_loop);
 
+bail:
     FURI_LOG_D(TAG, "Stopped");
     cli_shell_deinit(shell);
     return 0;