diff --git a/crates/gpui/src/platform/mac/window.rs b/crates/gpui/src/platform/mac/window.rs
index edd400d9fce3d1f61b8c40cdf4b10de7d9329a8b..09181d5766bc0f148f23cdf253d572258bceea37 100644
--- a/crates/gpui/src/platform/mac/window.rs
+++ b/crates/gpui/src/platform/mac/window.rs
@@ -1848,16 +1848,17 @@ extern "C" fn accepts_first_mouse(this: &Object, _: Sel, _: id) -> BOOL {
 
 extern "C" fn dragging_entered(this: &Object, _: Sel, dragging_info: id) -> NSDragOperation {
     let window_state = unsafe { get_window_state(this) };
-    if send_new_event(&window_state, {
-        let position = drag_event_position(&window_state, dragging_info);
-        let paths = external_paths_from_event(dragging_info);
-        PlatformInput::FileDrop(FileDropEvent::Entered { position, paths })
-    }) {
-        window_state.lock().external_files_dragged = true;
-        NSDragOperationCopy
-    } else {
-        NSDragOperationNone
+    let position = drag_event_position(&window_state, dragging_info);
+    let paths = external_paths_from_event(dragging_info);
+    if let Some(event) =
+        paths.map(|paths| PlatformInput::FileDrop(FileDropEvent::Entered { position, paths }))
+    {
+        if send_new_event(&window_state, event) {
+            window_state.lock().external_files_dragged = true;
+            return NSDragOperationCopy;
+        }
     }
+    NSDragOperationNone
 }
 
 extern "C" fn dragging_updated(this: &Object, _: Sel, dragging_info: id) -> NSDragOperation {
@@ -1895,10 +1896,13 @@ extern "C" fn perform_drag_operation(this: &Object, _: Sel, dragging_info: id) -
     }
 }
 
-fn external_paths_from_event(dragging_info: *mut Object) -> ExternalPaths {
+fn external_paths_from_event(dragging_info: *mut Object) -> Option<ExternalPaths> {
     let mut paths = SmallVec::new();
     let pasteboard: id = unsafe { msg_send![dragging_info, draggingPasteboard] };
     let filenames = unsafe { NSPasteboard::propertyListForType(pasteboard, NSFilenamesPboardType) };
+    if filenames == nil {
+        return None;
+    }
     for file in unsafe { filenames.iter() } {
         let path = unsafe {
             let f = NSString::UTF8String(file);
@@ -1906,7 +1910,7 @@ fn external_paths_from_event(dragging_info: *mut Object) -> ExternalPaths {
         };
         paths.push(PathBuf::from(path))
     }
-    ExternalPaths(paths)
+    Some(ExternalPaths(paths))
 }
 
 extern "C" fn conclude_drag_operation(this: &Object, _: Sel, _: id) {