diff --git a/glfw/cocoa_platform.h b/glfw/cocoa_platform.h
index 9bc765cd6..1a712b0dd 100644
--- a/glfw/cocoa_platform.h
+++ b/glfw/cocoa_platform.h
@@ -179,6 +179,11 @@ typedef struct _GLFWwindowNS
     // Drag source state
     char** sourceMimes;     // Array of MIME type strings for drag source
     int sourceMimeCount;    // Number of source MIME types
+
+    // Pending drag source data requests (for cleanup on cancellation)
+    GLFWDragSourceData** pendingDragSourceData;
+    int pendingDragSourceDataCount;
+    int pendingDragSourceDataCapacity;
 } _GLFWwindowNS;
 
 // Cocoa-specific global data
diff --git a/glfw/cocoa_window.m b/glfw/cocoa_window.m
index 33a9dda5c..0d40fe400 100644
--- a/glfw/cocoa_window.m
+++ b/glfw/cocoa_window.m
@@ -770,6 +770,92 @@ typedef struct {
     int errorCode;                       // Error code if any
 } GLFWFilePromiseState;
 
+// Helper function to clean up a single drag source data
+static void
+cleanup_ns_drag_source_data(GLFWDragSourceData* data) {
+    if (!data) return;
+    if (data->platform_data) {
+        GLFWFilePromiseState* state = (GLFWFilePromiseState*)data->platform_data;
+        // If the data wasn't finished, call completion with error
+        if (!data->finished && state->completionHandler) {
+            NSError* error = [NSError errorWithDomain:NSPOSIXErrorDomain code:ECANCELED userInfo:nil];
+            state->completionHandler(error);
+            Block_release(state->completionHandler);
+            state->completionHandler = nil;
+        }
+        if (state->fileHandle) {
+            @try {
+                [state->fileHandle closeFile];
+            } @catch (NSException* e) {
+                (void)e;
+            }
+            [state->fileHandle release];
+            state->fileHandle = nil;
+        }
+        if (state->destinationURL) {
+            [state->destinationURL release];
+            state->destinationURL = nil;
+        }
+        free(state);
+    }
+    free(data->mime_type);
+    free(data);
+}
+
+// Add a drag source data to the pending array for tracking
+static bool
+add_ns_pending_drag_source_data(_GLFWwindow* window, GLFWDragSourceData* data) {
+    if (!window || !data) return false;
+
+    // Grow array if needed
+    if (window->ns.pendingDragSourceDataCount >= window->ns.pendingDragSourceDataCapacity) {
+        // Cap maximum capacity to prevent excessive memory use
+        if (window->ns.pendingDragSourceDataCapacity >= 512) {
+            return false;
+        }
+        int new_capacity = window->ns.pendingDragSourceDataCapacity ? window->ns.pendingDragSourceDataCapacity * 2 : 4;
+        GLFWDragSourceData** new_array = realloc(window->ns.pendingDragSourceData,
+                                                  new_capacity * sizeof(GLFWDragSourceData*));
+        if (!new_array) return false;
+        window->ns.pendingDragSourceData = new_array;
+        window->ns.pendingDragSourceDataCapacity = new_capacity;
+    }
+
+    window->ns.pendingDragSourceData[window->ns.pendingDragSourceDataCount++] = data;
+    return true;
+}
+
+// Remove a specific drag source data from the pending array
+static void
+remove_ns_pending_drag_source_data(_GLFWwindow* window, GLFWDragSourceData* data) {
+    if (!window || !data) return;
+
+    for (int i = 0; i < window->ns.pendingDragSourceDataCount; i++) {
+        if (window->ns.pendingDragSourceData[i] == data) {
+            // Shift remaining elements
+            for (int j = i; j < window->ns.pendingDragSourceDataCount - 1; j++) {
+                window->ns.pendingDragSourceData[j] = window->ns.pendingDragSourceData[j + 1];
+            }
+            window->ns.pendingDragSourceDataCount--;
+            return;
+        }
+    }
+}
+
+// Clean up all pending drag source data for a window
+static void
+cleanup_all_ns_pending_drag_source_data(_GLFWwindow* window) {
+    if (!window) return;
+
+    for (int i = 0; i < window->ns.pendingDragSourceDataCount; i++) {
+        cleanup_ns_drag_source_data(window->ns.pendingDragSourceData[i]);
+    }
+    free(window->ns.pendingDragSourceData);
+    window->ns.pendingDragSourceData = NULL;
+    window->ns.pendingDragSourceDataCount = 0;
+    window->ns.pendingDragSourceDataCapacity = 0;
+}
+
 @interface GLFWFilePromiseProviderDelegate : NSObject <NSFilePromiseProviderDelegate>
 {
     GLFWid windowId;
@@ -876,6 +962,16 @@ typedef struct {
         return;
     }
 
+    // Track this source data for cleanup on cancellation
+    if (!add_ns_pending_drag_source_data(window, source_data)) {
+        // Call completion handler with memory error before cleanup
+        completionHandler([NSError errorWithDomain:NSPOSIXErrorDomain code:ENOMEM userInfo:nil]);
+        // Mark as finished to prevent cleanup_ns_drag_source_data from calling completionHandler again
+        source_data->finished = true;
+        cleanup_ns_drag_source_data(source_data);
+        return;
+    }
+
     // Notify the application via callback - this will trigger glfwSendDragData calls
     _glfwInputDragSourceRequest(window, mimeType, source_data);
 
@@ -1656,7 +1752,10 @@ static void freeFilteredDragMimes(_GLFWwindow* window, int old_count, int new_co
     drop_data->eof_reached = false;
     drop_data->current_data = NULL;
     drop_data->data_offset = 0;
-    _glfwInputDrop(window, drop_data);
+    // Check if the drop is from this application
+    // draggingSource returns the source object if the drag started in this application
+    bool from_self = ([sender draggingSource] != nil);
+    _glfwInputDrop(window, drop_data, from_self);
     // Note: drop_data is NOT freed here - application must call glfwFinishDrop
     return YES;
 }
@@ -1685,6 +1784,8 @@ static void freeFilteredDragMimes(_GLFWwindow* window, int old_count, int new_co
     (void)session;
     (void)screenPoint;
     (void)operation;
+    // Clean up all pending drag source data
+    cleanup_all_ns_pending_drag_source_data(window);
     // Notify the application that the drag source is closed
     _glfwInputDragSourceRequest(window, NULL, NULL);
     // Clean up source MIME types
@@ -3908,6 +4009,8 @@ void _glfwCocoaPostEmptyEvent(void) {
 }
 
 void _glfwPlatformCancelDrag(_GLFWwindow* window) {
+    // Clean up all pending drag source data
+    cleanup_all_ns_pending_drag_source_data(window);
     // Clean up source MIME types
     for (int i = 0; i < window->ns.sourceMimeCount; i++) {
         free(window->ns.sourceMimes[i]);
@@ -4056,11 +4159,13 @@ ssize_t _glfwPlatformSendDragData(GLFWDragSourceData* source_data, const void* d
             state->completionHandler = nil;
         }
 
-        // Clean up
-        [state->fileHandle release];
-        state->fileHandle = nil;
-        [state->destinationURL release];
-        state->destinationURL = nil;
+        // Remove from pending list and clean up
+        _GLFWwindow* window = _glfwWindowForId(source_data->window_id);
+        if (window) {
+            remove_ns_pending_drag_source_data(window, source_data);
+        }
+        // source_data->finished is true, so cleanup_ns_drag_source_data won't call completionHandler again
+        cleanup_ns_drag_source_data(source_data);
 
         return 0;
     }
@@ -4086,11 +4191,13 @@ ssize_t _glfwPlatformSendDragData(GLFWDragSourceData* source_data, const void* d
             state->completionHandler = nil;
         }
 
-        // Clean up
-        [state->fileHandle release];
-        state->fileHandle = nil;
-        [state->destinationURL release];
-        state->destinationURL = nil;
+        // Remove from pending list and clean up
+        _GLFWwindow* window = _glfwWindowForId(source_data->window_id);
+        if (window) {
+            remove_ns_pending_drag_source_data(window, source_data);
+        }
+        // source_data->finished is true, so cleanup_ns_drag_source_data won't call completionHandler again
+        cleanup_ns_drag_source_data(source_data);
 
         return 0;
     }
diff --git a/glfw/glfw3.h b/glfw/glfw3.h
index 01bc953a4..3031dfedb 100644
--- a/glfw/glfw3.h
+++ b/glfw/glfw3.h
@@ -1800,6 +1800,12 @@ typedef void (* GLFWkeyboardfun)(GLFWwindow*, GLFWkeyevent*);
  *  responsible for calling glfwFinishDrop when it has finished reading
  *  the dropped data, even if reading fails or is not needed.
  *
+ *  @param[in] window The window that received the drop.
+ *  @param[in] drop Opaque drop data pointer (heap-allocated).
+ *  @param[in] from_self true if the drop originated from this application
+ *  (i.e., the application is both the drag source and drop target), false
+ *  if the drop came from an external application.
+ *
  *  @sa @ref path_drop
  *  @sa @ref glfwSetDropCallback
  *  @sa @ref glfwGetDropMimeTypes
@@ -1807,10 +1813,11 @@ typedef void (* GLFWkeyboardfun)(GLFWwindow*, GLFWkeyevent*);
  *  @sa @ref glfwFinishDrop
  *
  *  @since Changed in version 4.0 to receive opaque drop data pointer.
+ *  @since Changed in version 4.0 to receive from_self parameter.
  *
  *  @ingroup input
  */
-typedef void (* GLFWdropfun)(GLFWwindow*, GLFWDropData*);
+typedef void (* GLFWdropfun)(GLFWwindow*, GLFWDropData*, bool from_self);
 
 /*! @brief Drag event types.
  *
diff --git a/glfw/input.c b/glfw/input.c
index 86667c544..b5b1a8564 100644
--- a/glfw/input.c
+++ b/glfw/input.c
@@ -404,10 +404,10 @@ void _glfwInputCursorEnter(_GLFWwindow* window, bool entered)
 
 // Notifies shared code of files or directories dropped on a window
 //
-void _glfwInputDrop(_GLFWwindow* window, GLFWDropData* drop)
+void _glfwInputDrop(_GLFWwindow* window, GLFWDropData* drop, bool from_self)
 {
     if (window->callbacks.drop)
-        window->callbacks.drop((GLFWwindow*) window, drop);
+        window->callbacks.drop((GLFWwindow*) window, drop, from_self);
 }
 
 // Notifies shared code of a drag event
diff --git a/glfw/internal.h b/glfw/internal.h
index a946b34aa..5ae8321c3 100644
--- a/glfw/internal.h
+++ b/glfw/internal.h
@@ -857,7 +857,7 @@ void _glfwInputScroll(_GLFWwindow* window, const GLFWScrollEvent *ev);
 void _glfwInputMouseClick(_GLFWwindow* window, int button, int action, int mods);
 void _glfwInputCursorPos(_GLFWwindow* window, double xpos, double ypos);
 void _glfwInputCursorEnter(_GLFWwindow* window, bool entered);
-void _glfwInputDrop(_GLFWwindow* window, GLFWDropData* drop);
+void _glfwInputDrop(_GLFWwindow* window, GLFWDropData* drop, bool from_self);
 int _glfwInputDragEvent(_GLFWwindow* window, int event, double xpos, double ypos, const char** mime_types, int* mime_count);
 void _glfwInputDragSourceRequest(_GLFWwindow* window, const char* mime_type, GLFWDragSourceData* source_data);
 
diff --git a/glfw/wl_platform.h b/glfw/wl_platform.h
index 87a5b37df..755728425 100644
--- a/glfw/wl_platform.h
+++ b/glfw/wl_platform.h
@@ -415,7 +415,9 @@ typedef struct _GLFWlibraryWayland
         char** mimes;           // Array of MIME type strings
         int mime_count;         // Number of MIME types
         GLFWid window_id;    // Window that initiated the drag
-        GLFWDragSourceData* current_request; // Current data request being processed
+        GLFWDragSourceData** pending_requests; // Array of pending data requests
+        int pending_request_count;  // Number of pending requests
+        int pending_request_capacity; // Capacity of the pending requests array
         struct wl_surface *drag_icon;
         struct wp_viewport *drag_viewport;
     } drag;
diff --git a/glfw/wl_window.c b/glfw/wl_window.c
index 4afae0ae6..696703bf8 100644
--- a/glfw/wl_window.c
+++ b/glfw/wl_window.c
@@ -2554,7 +2554,9 @@ drop(void *data UNUSED, struct wl_data_device *wl_data_device UNUSED) {
                     destroy_data_offer(offer);
                     drop_data->eof_reached = false;
                     memset(offer, 0, sizeof(offer[0]));
-                    _glfwInputDrop(window, drop_data);
+                    // Check if the drop is from this application
+                    bool from_self = (_glfw.wl.drag.window_id != 0);
+                    _glfwInputDrop(window, drop_data, from_self);
                     // Note: drop_data is NOT freed here - application must call glfwFinishDrop
                     break;
                 }
@@ -3007,7 +3009,7 @@ GLFWAPI bool glfwWaylandBeep(GLFWwindow *handle) {
 // Drag operation implementation
 
 static void
-cleanup_drag_source_data(GLFWDragSourceData* data) {
+cleanup_wl_drag_source_data(GLFWDragSourceData* data) {
     if (!data) return;
     if (data->write_fd >= 0) {
         close(data->write_fd);
@@ -3017,17 +3019,74 @@ cleanup_drag_source_data(GLFWDragSourceData* data) {
     free(data);
 }
 
+// Remove a finished request from the pending requests array
+static void
+remove_wl_pending_request(int index) {
+    if (index < 0 || index >= _glfw.wl.drag.pending_request_count) return;
+
+    cleanup_wl_drag_source_data(_glfw.wl.drag.pending_requests[index]);
+
+    // Shift remaining elements
+    for (int i = index; i < _glfw.wl.drag.pending_request_count - 1; i++) {
+        _glfw.wl.drag.pending_requests[i] = _glfw.wl.drag.pending_requests[i + 1];
+    }
+    _glfw.wl.drag.pending_request_count--;
+}
+
+// Clean up all finished requests from the pending requests array
+static void
+cleanup_wl_finished_requests(void) {
+    for (int i = _glfw.wl.drag.pending_request_count - 1; i >= 0; i--) {
+        if (_glfw.wl.drag.pending_requests[i]->finished) {
+            remove_wl_pending_request(i);
+        }
+    }
+}
+
+// Clean up all pending requests
+static void
+cleanup_all_wl_pending_requests(void) {
+    for (int i = 0; i < _glfw.wl.drag.pending_request_count; i++) {
+        cleanup_wl_drag_source_data(_glfw.wl.drag.pending_requests[i]);
+    }
+    free(_glfw.wl.drag.pending_requests);
+    _glfw.wl.drag.pending_requests = NULL;
+    _glfw.wl.drag.pending_request_count = 0;
+    _glfw.wl.drag.pending_request_capacity = 0;
+}
+
+// Add a request to the pending requests array
+static bool
+add_wl_pending_request(GLFWDragSourceData* request) {
+    // First, clean up any finished requests to make room
+    cleanup_wl_finished_requests();
+
+    // Grow the array if necessary
+    if (_glfw.wl.drag.pending_request_count >= _glfw.wl.drag.pending_request_capacity) {
+        // Cap maximum capacity to prevent excessive memory use
+        if (_glfw.wl.drag.pending_request_capacity >= 512) {
+            return false;
+        }
+        int new_capacity = _glfw.wl.drag.pending_request_capacity ? _glfw.wl.drag.pending_request_capacity * 2 : 4;
+        GLFWDragSourceData** new_array = realloc(_glfw.wl.drag.pending_requests,
+                                                  new_capacity * sizeof(GLFWDragSourceData*));
+        if (!new_array) return false;
+        _glfw.wl.drag.pending_requests = new_array;
+        _glfw.wl.drag.pending_request_capacity = new_capacity;
+    }
+
+    _glfw.wl.drag.pending_requests[_glfw.wl.drag.pending_request_count++] = request;
+    return true;
+}
+
 static void
 cleanup_drag(struct wl_data_source *source) {
     // Notify the application that the drag source is closed
     _GLFWwindow *window = _glfwWindowForId(_glfw.wl.drag.window_id);
     if (window && window->callbacks.dragSource) _glfwInputDragSourceRequest(window, NULL, NULL);
 
-    // Clean up any pending data request
-    if (_glfw.wl.drag.current_request) {
-        cleanup_drag_source_data(_glfw.wl.drag.current_request);
-        _glfw.wl.drag.current_request = NULL;
-    }
+    // Clean up all pending data requests
+    cleanup_all_wl_pending_requests();
 
     // Clean up MIME type strings
     for (int i = 0; i < _glfw.wl.drag.mime_count; i++) free(_glfw.wl.drag.mimes[i]);
@@ -3065,13 +3124,15 @@ drag_source_send(void *data UNUSED, struct wl_data_source *source UNUSED, const
     request->error_code = 0;
 
     if (!request->mime_type) {
-        cleanup_drag_source_data(request);
+        cleanup_wl_drag_source_data(request);
         return;
     }
 
-    // Store as current request
-    if (_glfw.wl.drag.current_request) cleanup_drag_source_data(_glfw.wl.drag.current_request);
-    _glfw.wl.drag.current_request = request;
+    // Add to pending requests array
+    if (!add_wl_pending_request(request)) {
+        cleanup_wl_drag_source_data(request);
+        return;
+    }
 
     // Notify the application via callback
     _glfwInputDragSourceRequest(window, mime_type, request);
@@ -3210,6 +3271,8 @@ _glfwPlatformSendDragData(GLFWDragSourceData* source_data, const void* data, siz
         source_data->finished = true;
         close(source_data->write_fd);
         source_data->write_fd = -1;
+        // Clean up this and any other finished requests
+        cleanup_wl_finished_requests();
         return 0;
     }
 
@@ -3219,6 +3282,8 @@ _glfwPlatformSendDragData(GLFWDragSourceData* source_data, const void* data, siz
         source_data->error_code = (int)size;
         close(source_data->write_fd);
         source_data->write_fd = -1;
+        // Clean up this and any other finished requests
+        cleanup_wl_finished_requests();
         return 0;
     }
 
@@ -3238,6 +3303,8 @@ _glfwPlatformSendDragData(GLFWDragSourceData* source_data, const void* data, siz
         source_data->error_code = errno;
         close(source_data->write_fd);
         source_data->write_fd = -1;
+        // Clean up this and any other finished requests
+        cleanup_wl_finished_requests();
         return -errno;
     }
 
diff --git a/glfw/x11_platform.h b/glfw/x11_platform.h
index 462a11c58..2fa08c036 100644
--- a/glfw/x11_platform.h
+++ b/glfw/x11_platform.h
@@ -400,7 +400,9 @@ typedef struct _GLFWlibraryX11
         Atom             action_atom;   // XdndActionCopy, XdndActionMove, or XdndActionLink
         bool             active;
         _GLFWwindow*     window;        // Window that initiated the drag
-        GLFWDragSourceData* current_request; // Current data request being processed
+        GLFWDragSourceData** pending_requests; // Array of pending data requests
+        int              pending_request_count;  // Number of pending requests
+        int              pending_request_capacity; // Capacity of the pending requests array
     } drag;
 
     struct {
diff --git a/glfw/x11_window.c b/glfw/x11_window.c
index 91c765e6c..019fcafc7 100644
--- a/glfw/x11_window.c
+++ b/glfw/x11_window.c
@@ -88,6 +88,10 @@ x11_cancel_momentum_scroll_timer(void) {
 
 #define _GLFW_XDND_VERSION 5
 
+// Forward declarations for drag source data handling
+static void cleanup_x11_drag_source_data(GLFWDragSourceData* data);
+static bool add_x11_pending_request(GLFWDragSourceData* request);
+
 // Wait for data to arrive using poll
 // This avoids blocking other threads via the per-display Xlib lock that also
 // covers GLX functions
@@ -1101,13 +1105,97 @@ static void handleSelectionRequest(XEvent* event)
     const XSelectionRequestEvent* request = &event->xselectionrequest;
 
     XEvent reply = { SelectionNotify };
-    reply.xselection.property = writeTargetToProperty(request);
     reply.xselection.display = request->display;
     reply.xselection.requestor = request->requestor;
     reply.xselection.selection = request->selection;
     reply.xselection.target = request->target;
     reply.xselection.time = request->time;
 
+    // Handle XdndSelection (drag and drop) specially
+    if (request->selection == _glfw.x11.XdndSelection && _glfw.x11.drag.active && _glfw.x11.drag.window) {
+        // Handle TARGETS request for XdndSelection
+        if (request->target == _glfw.x11.TARGETS) {
+            // Return the list of supported MIME type atoms
+            Atom *targets = calloc(_glfw.x11.drag.mime_count + 2, sizeof(Atom));
+            if (targets) {
+                targets[0] = _glfw.x11.TARGETS;
+                targets[1] = _glfw.x11.MULTIPLE;
+                for (int i = 0; i < _glfw.x11.drag.mime_count; i++) {
+                    targets[i + 2] = _glfw.x11.drag.type_atoms[i];
+                }
+                XChangeProperty(_glfw.x11.display,
+                                request->requestor,
+                                request->property,
+                                XA_ATOM,
+                                32,
+                                PropModeReplace,
+                                (unsigned char*)targets,
+                                _glfw.x11.drag.mime_count + 2);
+                free(targets);
+                reply.xselection.property = request->property;
+            } else {
+                reply.xselection.property = None;
+            }
+        } else {
+            // Find the matching MIME type for the requested target
+            const char* mime_type = NULL;
+            for (int i = 0; i < _glfw.x11.drag.mime_count; i++) {
+                if (_glfw.x11.drag.type_atoms[i] == request->target) {
+                    mime_type = _glfw.x11.drag.mimes[i];
+                    break;
+                }
+            }
+
+            if (mime_type) {
+                // Create a drag source data request
+                GLFWDragSourceData* source_data = calloc(1, sizeof(GLFWDragSourceData));
+                if (source_data) {
+                    source_data->window_id = _glfw.x11.drag.window->id;
+                    source_data->mime_type = _glfw_strdup(mime_type);
+                    source_data->write_fd = -1;
+                    source_data->finished = false;
+                    source_data->error_code = 0;
+                    // Store request info in platform_data for later use
+                    // We'll use a simple struct to hold the X11-specific data
+                    struct {
+                        Window requestor;
+                        Atom property;
+                        Atom target;
+                    } *x11_data = malloc(sizeof(*x11_data));
+                    if (x11_data && source_data->mime_type) {
+                        x11_data->requestor = request->requestor;
+                        x11_data->property = request->property;
+                        x11_data->target = request->target;
+                        source_data->platform_data = x11_data;
+
+                        if (add_x11_pending_request(source_data)) {
+                            // Notify the application via callback
+                            _glfwInputDragSourceRequest(_glfw.x11.drag.window, mime_type, source_data);
+                            reply.xselection.property = request->property;
+                        } else {
+                            free(x11_data);
+                            free(source_data->mime_type);
+                            free(source_data);
+                            reply.xselection.property = None;
+                        }
+                    } else {
+                        free(x11_data);
+                        free(source_data->mime_type);
+                        free(source_data);
+                        reply.xselection.property = None;
+                    }
+                } else {
+                    reply.xselection.property = None;
+                }
+            } else {
+                reply.xselection.property = None;
+            }
+        }
+    } else {
+        // Handle regular clipboard/primary selection
+        reply.xselection.property = writeTargetToProperty(request);
+    }
+
     XSendEvent(_glfw.x11.display, request->requestor, False, 0, &reply);
 }
 
@@ -1974,7 +2062,10 @@ static void processEvent(XEvent *event)
                     drop_data->x11_source = _glfw.x11.xdnd.source;
                     drop_data->x11_version = _glfw.x11.xdnd.version;
 
-                    _glfwInputDrop(window, drop_data);
+                    // Check if the drop is from this application
+                    bool from_self = (_glfw.x11.drag.source_window != None &&
+                                      _glfw.x11.xdnd.source == _glfw.x11.drag.source_window);
+                    _glfwInputDrop(window, drop_data, from_self);
 
                     // Note: drop_data is NOT freed here - application must call glfwFinishDrop
                 }
@@ -3717,21 +3808,79 @@ static void cleanup_x11_drag_source_data(GLFWDragSourceData* data) {
         close(data->write_fd);
         data->write_fd = -1;
     }
+    free(data->platform_data);
     free(data->mime_type);
     free(data);
 }
 
+// Remove a finished request from the pending requests array
+static void
+remove_x11_pending_request(int index) {
+    if (index < 0 || index >= _glfw.x11.drag.pending_request_count) return;
+
+    cleanup_x11_drag_source_data(_glfw.x11.drag.pending_requests[index]);
+
+    // Shift remaining elements
+    for (int i = index; i < _glfw.x11.drag.pending_request_count - 1; i++) {
+        _glfw.x11.drag.pending_requests[i] = _glfw.x11.drag.pending_requests[i + 1];
+    }
+    _glfw.x11.drag.pending_request_count--;
+}
+
+// Clean up all finished requests from the pending requests array
+static void
+cleanup_x11_finished_requests(void) {
+    for (int i = _glfw.x11.drag.pending_request_count - 1; i >= 0; i--) {
+        if (_glfw.x11.drag.pending_requests[i]->finished) {
+            remove_x11_pending_request(i);
+        }
+    }
+}
+
+// Clean up all pending requests
+static void
+cleanup_all_x11_pending_requests(void) {
+    for (int i = 0; i < _glfw.x11.drag.pending_request_count; i++) {
+        cleanup_x11_drag_source_data(_glfw.x11.drag.pending_requests[i]);
+    }
+    free(_glfw.x11.drag.pending_requests);
+    _glfw.x11.drag.pending_requests = NULL;
+    _glfw.x11.drag.pending_request_count = 0;
+    _glfw.x11.drag.pending_request_capacity = 0;
+}
+
+// Add a request to the pending requests array
+static bool
+add_x11_pending_request(GLFWDragSourceData* request) {
+    // First, clean up any finished requests to make room
+    cleanup_x11_finished_requests();
+
+    // Grow the array if necessary
+    if (_glfw.x11.drag.pending_request_count >= _glfw.x11.drag.pending_request_capacity) {
+        // Cap maximum capacity to prevent excessive memory use
+        if (_glfw.x11.drag.pending_request_capacity >= 512) {
+            return false;
+        }
+        int new_capacity = _glfw.x11.drag.pending_request_capacity ? _glfw.x11.drag.pending_request_capacity * 2 : 4;
+        GLFWDragSourceData** new_array = realloc(_glfw.x11.drag.pending_requests,
+                                                  new_capacity * sizeof(GLFWDragSourceData*));
+        if (!new_array) return false;
+        _glfw.x11.drag.pending_requests = new_array;
+        _glfw.x11.drag.pending_request_capacity = new_capacity;
+    }
+
+    _glfw.x11.drag.pending_requests[_glfw.x11.drag.pending_request_count++] = request;
+    return true;
+}
+
 static void cleanupDragSource(void) {
     // Notify the application that the drag source is closed
     if (_glfw.x11.drag.window && _glfw.x11.drag.window->callbacks.dragSource) {
         _glfwInputDragSourceRequest(_glfw.x11.drag.window, NULL, NULL);
     }
 
-    // Clean up any pending data request
-    if (_glfw.x11.drag.current_request) {
-        cleanup_x11_drag_source_data(_glfw.x11.drag.current_request);
-        _glfw.x11.drag.current_request = NULL;
-    }
+    // Clean up all pending data requests
+    cleanup_all_x11_pending_requests();
 
     // Clean up MIME type strings and atoms
     for (int i = 0; i < _glfw.x11.drag.mime_count; i++) {
@@ -3834,8 +3983,7 @@ int _glfwPlatformStartDrag(_GLFWwindow* window,
 ssize_t _glfwPlatformSendDragData(GLFWDragSourceData* source_data, const void* data, size_t size) {
     if (!source_data || source_data->finished) return -EINVAL;
 
-    // For X11, we typically set properties for SelectionRequest events
-    // The write_fd is used if we set up a pipe-based transfer
+    // For X11, we set properties via XChangeProperty in response to SelectionRequest
 
     // End of data: NULL data pointer and size zero
     if (!data && size == 0) {
@@ -3844,6 +3992,8 @@ ssize_t _glfwPlatformSendDragData(GLFWDragSourceData* source_data, const void* d
             close(source_data->write_fd);
             source_data->write_fd = -1;
         }
+        // Clean up this and any other finished requests
+        cleanup_x11_finished_requests();
         return 0;
     }
 
@@ -3855,12 +4005,36 @@ ssize_t _glfwPlatformSendDragData(GLFWDragSourceData* source_data, const void* d
             close(source_data->write_fd);
             source_data->write_fd = -1;
         }
+        // Clean up this and any other finished requests
+        cleanup_x11_finished_requests();
         return 0;
     }
 
-    // For X11, data is typically set via XChangeProperty in response to SelectionRequest
-    // Store the data in platform_data for the SelectionRequest handler
-    // Non-blocking write - retry on EINTR, return 0 on would-block
+    // For X11, use XChangeProperty to set the data on the requestor window
+    if (source_data->platform_data) {
+        struct {
+            Window requestor;
+            Atom property;
+            Atom target;
+        } *x11_data = source_data->platform_data;
+
+        XChangeProperty(_glfw.x11.display,
+                        x11_data->requestor,
+                        x11_data->property,
+                        x11_data->target,
+                        8,
+                        PropModeReplace,
+                        (unsigned char*)data,
+                        size);
+        XFlush(_glfw.x11.display);
+
+        // Mark as finished after sending data
+        source_data->finished = true;
+        cleanup_x11_finished_requests();
+        return (ssize_t)size;
+    }
+
+    // Fallback: Non-blocking write if we have an fd
     if (source_data->write_fd >= 0) {
         ssize_t written;
         do {
@@ -3876,13 +4050,15 @@ ssize_t _glfwPlatformSendDragData(GLFWDragSourceData* source_data, const void* d
             source_data->error_code = errno;
             close(source_data->write_fd);
             source_data->write_fd = -1;
+            // Clean up this and any other finished requests
+            cleanup_x11_finished_requests();
             return -errno;
         }
         return written;
     }
 
-    // No fd available, all data is accepted (buffered by platform_data)
-    return (ssize_t)size;
+    // No valid mechanism to send data
+    return -EINVAL;
 }
 
 void _glfwPlatformUpdateDragState(_GLFWwindow* window) {
diff --git a/kitty/glfw-wrapper.h b/kitty/glfw-wrapper.h
index a48ff16dc..bae5f4b43 100644
--- a/kitty/glfw-wrapper.h
+++ b/kitty/glfw-wrapper.h
@@ -1535,10 +1535,11 @@ typedef void (* GLFWkeyboardfun)(GLFWwindow*, GLFWkeyevent*);
  *  @sa @ref glfwFinishDrop
  *
  *  @since Changed in version 4.0 to receive opaque drop data pointer.
+ *  @since Changed in version 4.0 to receive from_self parameter.
  *
  *  @ingroup input
  */
-typedef void (* GLFWdropfun)(GLFWwindow*, GLFWDropData*);
+typedef void (* GLFWdropfun)(GLFWwindow*, GLFWDropData*, bool from_self);
 
 /*! @brief Drag event types.
  *
diff --git a/kitty/glfw.c b/kitty/glfw.c
index b607ff8d3..74944e2f2 100644
--- a/kitty/glfw.c
+++ b/kitty/glfw.c
@@ -742,11 +742,20 @@ get_mime_data(GLFWDropData *drop, const char **mimes, int mime_count, PyObject *
 }
 
 static void
-drop_callback(GLFWwindow *w, GLFWDropData *drop) {
+drop_callback(GLFWwindow *w, GLFWDropData *drop, bool from_self) {
     int num_mimes;
     const char** mimes = glfwGetDropMimeTypes(drop, &num_mimes);
     RAII_PyObject(ans, PyDict_New());
-    get_mime_data(drop, mimes, num_mimes, ans);
+    if (from_self && global_state.drag_source.drag_data) {
+        // For self-drops, copy data directly from drag_source.drag_data
+        PyObject *key, *value;
+        Py_ssize_t pos = 0;
+        while (PyDict_Next(global_state.drag_source.drag_data, &pos, &key, &value)) {
+            if (PyDict_SetItem(ans, key, value) != 0) break;
+        }
+    } else {
+        get_mime_data(drop, mimes, num_mimes, ans);
+    }
     RAII_PyObject(exc, PyErr_GetRaisedException());
     glfwFinishDrop(drop, GLFW_DRAG_OPERATION_COPY, true);
     if (!set_callback_window(w)) return;