diff --git a/frontend/menu/menu_common.c b/frontend/menu/menu_common.c
index 674e2252f3..164c38905e 100644
--- a/frontend/menu/menu_common.c
+++ b/frontend/menu/menu_common.c
@@ -623,12 +623,14 @@ static int menu_custom_bind_iterate_keyboard(void *data, unsigned action)
    if (driver.video_data && driver.menu_ctx && driver.menu_ctx->render_messagebox)
       driver.menu_ctx->render_messagebox(rgui, msg);
 
+   bool timed_out = false;
    if (timeout <= 0)
    {
       rgui->binds.begin++;
       rgui->binds.target->key = RETROK_UNKNOWN; // Could be unsafe, but whatever.
       rgui->binds.target++;
       rgui->binds.timeout_end = rarch_get_time_usec() + RGUI_KEYBOARD_BIND_TIMEOUT_SECONDS * 1000000;
+      timed_out = true;
    }
 
    // binds.begin is updated in keyboard_press callback.
@@ -639,7 +641,10 @@ static int menu_custom_bind_iterate_keyboard(void *data, unsigned action)
       // Avoid new binds triggering things right away.
       rgui->trigger_state = 0;
       rgui->old_input_state = -1ULL;
-      input_keyboard_wait_keys_cancel();
+
+      // We won't be getting any key events, so just cancel early.
+      if (timed_out)
+         input_keyboard_wait_keys_cancel();
    }
    return 0;
 }
diff --git a/input/keyboard_line.c b/input/keyboard_line.c
index 0e31efb828..c5835a1291 100644
--- a/input/keyboard_line.c
+++ b/input/keyboard_line.c
@@ -130,10 +130,17 @@ void input_keyboard_wait_keys_cancel(void)
 
 void input_keyboard_event(bool down, unsigned code, uint32_t character, uint16_t mod)
 {
-   if (g_keyboard_press_cb)
+   static bool deferred_wait_keys;
+
+   if (deferred_wait_keys)
+   {
+      input_keyboard_wait_keys_cancel();
+      deferred_wait_keys = false;
+   }
+   else if (g_keyboard_press_cb)
    {
       if (down && code != RETROK_UNKNOWN && !g_keyboard_press_cb(g_keyboard_press_data, code))
-         input_keyboard_wait_keys_cancel();
+         deferred_wait_keys = true;
    }
    else if (g_keyboard_line)
    {