diff --git a/glfw/cocoa_window.m b/glfw/cocoa_window.m
index e8fc090e7..8fe492af5 100644
--- a/glfw/cocoa_window.m
+++ b/glfw/cocoa_window.m
@@ -4215,7 +4215,8 @@ _glfwPlatformFreeDragSourceData(void) {
 }
 
 int
-_glfwPlatformChangeDragImage(const GLFWimage *thumbnail) {@autoreleasepool{
+_glfwPlatformChangeDragImage(const GLFWimage *thumbnail, int make_toplevel) {@autoreleasepool{
+    (void)make_toplevel;
     if (!_glfw.ns.drag_session || !_glfw.ns.drag_view) return 0;
     _GLFWwindow *window = _glfwWindowForId(_glfw.drag.window_id);
     NSArray *classes = @[[NSPasteboardItem class], [NSFilePromiseProvider class]];
diff --git a/glfw/input.c b/glfw/input.c
index 0518a39dc..3a03e505f 100644
--- a/glfw/input.c
+++ b/glfw/input.c
@@ -1166,7 +1166,7 @@ glfwStartDrag(GLFWwindow* handle, const GLFWDragSourceItem *items, size_t item_c
     assert(window != NULL);
     _GLFW_REQUIRE_INIT_OR_RETURN(EINVAL);
     if (operations == -1) return _glfwPlatformDragDataReady(items[0].mime_type);
-    if (operations == -2) return _glfwPlatformChangeDragImage(thumbnail);
+    if (operations == -2) return _glfwPlatformChangeDragImage(thumbnail, item_count);
     _glfwFreeDragSourceData();
     _glfw.drag.instance_id++;
     if (!items || !item_count) return 0;
diff --git a/glfw/internal.h b/glfw/internal.h
index d7e58e50a..b377e3ef7 100644
--- a/glfw/internal.h
+++ b/glfw/internal.h
@@ -837,7 +837,7 @@ void _glfwFreeDragSourceData(void);
 void _glfwPlatformFreeDragSourceData(void);
 void _glfwInputDragSourceRequest(_GLFWwindow* window, GLFWDragEvent *ev);
 int _glfwPlatformDragDataReady(const char *mime_type);
-int _glfwPlatformChangeDragImage(const GLFWimage *thumbnail);
+int _glfwPlatformChangeDragImage(const GLFWimage *thumbnail, int make_toplevel);
 
 
 void _glfwInputColorScheme(GLFWColorScheme, bool);
diff --git a/glfw/null_window.c b/glfw/null_window.c
index b46279c9d..675332f34 100644
--- a/glfw/null_window.c
+++ b/glfw/null_window.c
@@ -542,7 +542,7 @@ _glfwPlatformStartDrag(_GLFWwindow* window, const GLFWimage* thumbnail) {
 }
 void _glfwPlatformFreeDragSourceData(void) {}
 int _glfwPlatformDragDataReady(const char *mime_type) { (void) mime_type; return 0; }
-int _glfwPlatformChangeDragImage(const GLFWimage *thumbnail) { (void)thumbnail; return 0; }
+int _glfwPlatformChangeDragImage(const GLFWimage *thumbnail, int make_toplevel) { (void)thumbnail; (void)make_toplevel; return 0; }
 
 const char** _glfwPlatformGetDropMimeTypes(GLFWDropData* drop UNUSED, int* count)
 {
diff --git a/glfw/wl_window.c b/glfw/wl_window.c
index 511b7807d..763ee6ce4 100644
--- a/glfw/wl_window.c
+++ b/glfw/wl_window.c
@@ -3190,7 +3190,8 @@ add_drag_watch(int fd) {
 }
 
 int
-_glfwPlatformChangeDragImage(const GLFWimage *thumbnail) {
+_glfwPlatformChangeDragImage(const GLFWimage *thumbnail, int make_toplevel) {
+    (void)make_toplevel;  // TODO: Implement me
     if (!_glfw.wl.drag.drag_icon || !thumbnail || !thumbnail->pixels) return 0;
     struct wl_buffer* icon_buffer = createShmBuffer(thumbnail, false, true);
     if (!icon_buffer) return ENOMEM;
@@ -3353,9 +3354,9 @@ _glfwPlatformStartDrag(_GLFWwindow* window, const GLFWimage* thumbnail) {
     wl_data_source_add_listener(_glfw.wl.drag.source, &drag_source_listener, NULL);
 
     // Set up the drag icon surface if thumbnail is provided
+    _glfw.wl.drag.drag_icon = wl_compositor_create_surface(_glfw.wl.compositor);
     if (thumbnail && thumbnail->pixels) {
         struct wl_buffer* icon_buffer = NULL;
-        _glfw.wl.drag.drag_icon = wl_compositor_create_surface(_glfw.wl.compositor);
         if (_glfw.wl.drag.drag_icon) {
             icon_buffer = createShmBuffer(thumbnail, false, true);
             if (icon_buffer) {
diff --git a/glfw/x11_window.c b/glfw/x11_window.c
index 5d52d5e91..4ced436db 100644
--- a/glfw/x11_window.c
+++ b/glfw/x11_window.c
@@ -4471,7 +4471,8 @@ _glfwPlatformFreeDragSourceData(void) {
 }
 
 int
-_glfwPlatformChangeDragImage(const GLFWimage *thumbnail) {
+_glfwPlatformChangeDragImage(const GLFWimage *thumbnail, int make_toplevel) {
+    (void)make_toplevel;
     if (!_glfw.x11.drag.active) return 0;
     if (!thumbnail || !thumbnail->pixels || thumbnail->width <= 0 || thumbnail->height <= 0) return 0;
 
diff --git a/kitty/boss.py b/kitty/boss.py
index 292e6dec5..aa70b5d9d 100644
--- a/kitty/boss.py
+++ b/kitty/boss.py
@@ -73,6 +73,7 @@ from .fast_data_types import (
     apply_options_update,
     background_opacity_of,
     change_background_opacity,
+    change_drag_thumbnail,
     cocoa_hide_app,
     cocoa_hide_other_apps,
     cocoa_minimize_os_window,
@@ -1900,6 +1901,8 @@ 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
+                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)
                     q.on_tab_drop_move(tab_id, is_dest, x, y)
@@ -3358,7 +3361,7 @@ class Boss:
             with open(logo_png_file, 'rb') as f:
                 rgba, width, height = load_png_data(f.read())
             drag_data = {'text/plain': b'This is a test drag of some basic text with the kitty logo as the drag icon.'}
-            start_drag_with_data(wid, drag_data, rgba, width, height)
+            start_drag_with_data(wid, drag_data, ((rgba, width, height),))
 
     def launch_urls(self, *urls: str, no_replace_window: bool = False) -> None:
         from .launch import force_window_launch
diff --git a/kitty/fast_data_types.pyi b/kitty/fast_data_types.pyi
index 08a13bbbf..98eb19bfb 100644
--- a/kitty/fast_data_types.pyi
+++ b/kitty/fast_data_types.pyi
@@ -1,5 +1,5 @@
 import termios
-from typing import Any, Callable, Dict, Iterator, List, Literal, NewType, Optional, Tuple, TypedDict, Union, overload
+from typing import Any, Callable, Dict, Iterator, List, Literal, NewType, Optional, Sequence, Tuple, TypedDict, Union, overload
 
 from kitty.borders import Border
 from kitty.boss import Boss
@@ -1814,10 +1814,10 @@ class StreamingBase64Encodeer:
 
 
 def start_drag_with_data(
-    os_window_id: int, data_map: dict[str, bytes], thumbnail: bytes = b'', width: int = 0, height: int = 0,
+    os_window_id: int, data_map: dict[str, bytes], thumbnails: Sequence[tuple[bytes, int, int]],
     operations: int = GLFW_DRAG_OPERATION_MOVE
 ) -> None: ...
-
+def change_drag_thumbnail(os_window_id: int, idx: int = -1, make_toplevel: bool = False) -> None: ...
 def draw_single_line_of_text(os_window_id: int, text: str, fg: int, bg: int, width: int, padding_y: int = 2) -> bytes: ...
 def set_tab_being_dragged(tab_id: int = 0, drag_started: bool = False, x: float = 0, y: float = 0) -> None: ...
 def get_tab_being_dragged() -> tuple[int, bool, float, float]: ...
diff --git a/kitty/glfw.c b/kitty/glfw.c
index 6e616237f..604b41dcf 100644
--- a/kitty/glfw.c
+++ b/kitty/glfw.c
@@ -784,7 +784,7 @@ application_close_requested_callback(int flags) {
 void
 free_drag_source(void) {
     if (ds.accepted_mime_type) free(ds.accepted_mime_type);
-    Py_CLEAR(ds.drag_data);
+    Py_CLEAR(ds.drag_data); Py_CLEAR(ds.thumbnails);
     zero_at_ptr(&ds);
 }
 
@@ -2787,16 +2787,49 @@ draw_single_line_of_text(PyObject *self UNUSED, PyObject *args) {
     return Py_NewRef(ans);
 }
 
+static bool
+get_thumbnail(PyObject *thumbnails, GLFWimage *thumbnail, int idx) {
+    RAII_PyObject(t, PySequence_GetItem(thumbnails, idx));
+    if (!PyTuple_Check(t) || PyTuple_GET_SIZE(t) != 3) { PyErr_SetString(PyExc_TypeError, "thumbnail must be a 3-tuple"); return false; }
+    thumbnail->pixels = (uint8_t*)PyBytes_AS_STRING(PyTuple_GET_ITEM(t, 0));
+    thumbnail->width = PyLong_AsUnsignedLong(PyTuple_GET_ITEM(t, 1));
+    thumbnail->height = PyLong_AsUnsignedLong(PyTuple_GET_ITEM(t, 2));
+    return true;
+}
+
 static PyObject*
-start_drag_with_data(PyObject *self UNUSED, PyObject *args, PyObject *kw) {
-    static const char* kwlist[] = {"os_window_id", "data_map", "thumbnail", "width", "height", "operations", NULL};
-    unsigned long long os_window_id; PyObject *data_map;
-    const unsigned char *thumbnail_data = NULL; Py_ssize_t thumbnail_sz = 0; int height = 0, width = 0;
-    int operations = GLFW_DRAG_OPERATION_MOVE;
-    if (!PyArg_ParseTupleAndKeywords(args, kw, "KO!|y#iii", (char**)kwlist,
-            &os_window_id, &PyDict_Type, &data_map, &thumbnail_data, &thumbnail_sz, &width, &height, &operations)) return NULL;
+change_drag_thumbnail(PyObject *self UNUSED, PyObject *args) {
+    unsigned long long os_window_id; int idx = -1; int make_toplevel = 0;
+    if (!PyArg_ParseTuple(args, "K|ip", &os_window_id, &idx, &make_toplevel)) return NULL;
+    if (global_state.drag_source.thumbnail_idx == idx) Py_RETURN_NONE;
     OSWindow *w = os_window_for_id(os_window_id);
     if (!w || !w->handle) { PyErr_SetString(PyExc_KeyError, "OS Window with specified id does not exist"); return NULL; }
+    GLFWimage thumbnail = {0};
+    if (idx >=0 && global_state.drag_source.thumbnails && idx < PySequence_Size(global_state.drag_source.thumbnails)) {
+        if (!get_thumbnail(global_state.drag_source.thumbnails, &thumbnail, idx)) return NULL;
+        global_state.drag_source.thumbnail_idx = idx;
+    } else global_state.drag_source.thumbnail_idx = -1;
+    errno = glfwStartDrag(w->handle, NULL, make_toplevel, thumbnail.pixels ? &thumbnail : NULL, -2);
+    if (errno != 0) {
+        PyErr_SetFromErrno(PyExc_OSError);
+        return NULL;
+    }
+    Py_RETURN_NONE;
+}
+
+static PyObject*
+start_drag_with_data(PyObject *self UNUSED, PyObject *args, PyObject *kw) {
+    static const char* kwlist[] = {"os_window_id", "data_map", "thumbnails", "operations", NULL};
+    unsigned long long os_window_id; PyObject *data_map;
+    int operations = GLFW_DRAG_OPERATION_MOVE;
+    PyObject *thumbnails = NULL;
+    if (!PyArg_ParseTupleAndKeywords(args, kw, "KO!|Oi", (char**)kwlist,
+            &os_window_id, &PyDict_Type, &data_map, &thumbnails, &operations)) return NULL;
+    OSWindow *w = os_window_for_id(os_window_id);
+    if (!w || !w->handle) { PyErr_SetString(PyExc_KeyError, "OS Window with specified id does not exist"); return NULL; }
+    GLFWimage thumbnail = {0};
+    if (!PySequence_Check(thumbnails)) { PyErr_SetString(PyExc_TypeError, "thumbnails must be a sequence"); return NULL; }
+    if (thumbnails && PySequence_Size(thumbnails) && !get_thumbnail(thumbnails, &thumbnail, 0)) return NULL;
     RAII_ALLOC(GLFWDragSourceItem, items, calloc(PyDict_Size(data_map), sizeof(GLFWDragSourceItem)));
     if (!items) { PyErr_NoMemory(); return NULL; }
     PyObject *key, *value; Py_ssize_t pos = 0; size_t num = 0;
@@ -2807,11 +2840,12 @@ start_drag_with_data(PyObject *self UNUSED, PyObject *args, PyObject *kw) {
         item->mime_type = PyUnicode_AsUTF8(key);
         item->optional_data = PyBytes_AS_STRING(value); item->data_size = PyBytes_GET_SIZE(value);
     }
-    GLFWimage thumbnail = {.pixels=thumbnail_data, .width=width, .height=height};
     free_drag_source();
     global_state.drag_source.is_active = true;
     global_state.drag_source.drag_data = Py_NewRef(data_map);
-    errno = glfwStartDrag(w->handle, items, num, thumbnail_data ? &thumbnail : NULL, operations);
+    if (thumbnails) global_state.drag_source.thumbnails = Py_NewRef(thumbnails);
+    global_state.drag_source.thumbnail_idx = thumbnail.pixels ? 0 : -1;
+    errno = glfwStartDrag(w->handle, items, num, thumbnail.pixels ? &thumbnail : NULL, operations);
     if (errno != 0) {
         PyErr_SetFromErrno(PyExc_OSError);
         return NULL;
@@ -2831,6 +2865,7 @@ static PyMethodDef module_methods[] = {
     METHODB(pointer_name_to_css_name, METH_O),
     {"create_os_window", (PyCFunction)(void (*) (void))(create_os_window), METH_VARARGS | METH_KEYWORDS, NULL},
     {"start_drag_with_data", (PyCFunction)(void (*) (void))(start_drag_with_data), METH_VARARGS | METH_KEYWORDS, NULL},
+    METHODB(change_drag_thumbnail, METH_VARARGS),
     METHODB(draw_single_line_of_text, METH_VARARGS),
     METHODB(set_default_window_icon, METH_VARARGS),
     METHODB(set_os_window_icon, METH_VARARGS),
diff --git a/kitty/state.h b/kitty/state.h
index 677b0560c..a2690a5ac 100644
--- a/kitty/state.h
+++ b/kitty/state.h
@@ -386,8 +386,8 @@ typedef struct GlobalState {
     struct {
         bool is_active, was_dropped, was_canceled;
         char *accepted_mime_type;
-        int action;
-        PyObject *drag_data;
+        int action, thumbnail_idx;
+        PyObject *drag_data, *thumbnails;
     } drag_source;
     struct {
         id_type os_window, window;
diff --git a/kitty/tabs.py b/kitty/tabs.py
index 82eda3947..42b7ae4b3 100644
--- a/kitty/tabs.py
+++ b/kitty/tabs.py
@@ -1654,10 +1654,11 @@ class TabManager:  # {{{
                     bg = color_as_int(opts.inactive_tab_background)
                 title_pixels = draw_single_line_of_text(self.os_window_id, title, 0xff000000 | fg, 0xff000000 | bg, width)
                 title_height = len(title_pixels) // (width * 4)
+                thumbnails = ((title_pixels, width, title_height), (title_pixels + pixels, width, title_height + height))
                 drag_data = {
                     f'application/net.kovidgoyal.kitty-tab-{os.getpid()}': str(tab.id).encode(),
                 }
-                start_drag_with_data(self.os_window_id, drag_data, title_pixels + pixels, width, title_height + height)
+                start_drag_with_data(self.os_window_id, drag_data, thumbnails)
                 break
         else:
             set_tab_being_dragged()