diff --git a/kitty/boss.py b/kitty/boss.py
index aa70b5d9d..f3a4a02e1 100644
--- a/kitty/boss.py
+++ b/kitty/boss.py
@@ -1893,7 +1893,7 @@ class Boss:
         if tm is not None:
             tm.update_tab_bar_data()
 
-    def on_drop_move(self, os_window_id: int, x: int, y: int, from_self: bool) -> None:
+    def on_drop_move(self, os_window_id: int, x: int, y: int, from_self: bool, is_leave: bool) -> None:
         if (tm := self.os_window_map.get(os_window_id)) is None:
             return
         if from_self:
@@ -1901,10 +1901,10 @@ class Boss:
             if tab_id and drag_started and (tab := self.tab_for_id(tab_id)):
                 central, tab_bar = viewport_for_window(os_window_id)[:2]
                 in_tab_bar = tab_bar.left <= x < tab_bar.right and tab_bar.top <= y < tab_bar.bottom
-                detach = not in_tab_bar or tab.os_window_id != tm.os_window_id
+                detach = not in_tab_bar or tab.os_window_id != tm.os_window_id or is_leave
                 change_drag_thumbnail(tab.os_window_id, 1 if detach else 0, detach)
                 for q in self.all_tab_managers:
-                    is_dest = q is tm and (in_tab_bar or os_window_id != tab.os_window_id)
+                    is_dest = q is tm and (in_tab_bar or os_window_id != tab.os_window_id) and not is_leave
                     q.on_tab_drop_move(tab_id, is_dest, x, y)
 
     def on_drop(self, os_window_id: int, drop: dict[str, bytes] | int, from_self: bool, x: int, y: int) -> None:
diff --git a/kitty/glfw.c b/kitty/glfw.c
index 604b41dcf..94e043f39 100644
--- a/kitty/glfw.c
+++ b/kitty/glfw.c
@@ -731,14 +731,17 @@ on_drop(GLFWwindow *window, GLFWDropEvent *ev) {
             os_window->last_drag_event.x = (int)(ev->xpos * os_window->viewport_x_ratio);
             os_window->last_drag_event.y = (int)(ev->ypos * os_window->viewport_y_ratio);
             on_mouse_position_update(ev->xpos, ev->ypos);
-            call_boss(on_drop_move, "KiiO",
+            call_boss(on_drop_move, "KiiOO",
                 os_window->id, os_window->last_drag_event.x, os_window->last_drag_event.y,
-                ev->from_self ? Py_True : Py_False);
+                ev->from_self ? Py_True : Py_False, Py_False);
             /* fallthrough */
         case GLFW_DROP_STATUS_UPDATE:
             update_allowed_mimes_for_drop(ev);
             break;
         case GLFW_DROP_LEAVE:
+            call_boss(on_drop_move, "KiiOO",
+                os_window->id, os_window->last_drag_event.x, os_window->last_drag_event.y,
+                ev->from_self ? Py_True : Py_False, Py_True);
             break;
         case GLFW_DROP_DROP:
             Py_CLEAR(global_state.drop_dest.data);