diff --git a/apps/code/src/main/preload.ts b/apps/code/src/main/preload.ts
index 88f4dfa96..51b354da7 100644
--- a/apps/code/src/main/preload.ts
+++ b/apps/code/src/main/preload.ts
@@ -1,6 +1,11 @@
 import { exposeElectronTRPC } from "@posthog/electron-trpc/main";
+import { contextBridge, webUtils } from "electron";
 import "electron-log/preload";
 
+contextBridge.exposeInMainWorld("electronUtils", {
+  getPathForFile: (file: File) => webUtils.getPathForFile(file),
+});
+
 process.once("loaded", async () => {
   exposeElectronTRPC();
 });
diff --git a/apps/code/src/renderer/features/message-editor/components/AttachmentMenu.tsx b/apps/code/src/renderer/features/message-editor/components/AttachmentMenu.tsx
index 73704b692..d9b4454cc 100644
--- a/apps/code/src/renderer/features/message-editor/components/AttachmentMenu.tsx
+++ b/apps/code/src/renderer/features/message-editor/components/AttachmentMenu.tsx
@@ -4,6 +4,7 @@ import { IconButton, Popover } from "@radix-ui/themes";
 import { trpcClient, useTRPC } from "@renderer/trpc/client";
 import { toast } from "@renderer/utils/toast";
 import { useQuery } from "@tanstack/react-query";
+import { getFilePath } from "@utils/getFilePath";
 import { getFileName } from "@utils/path";
 import { useRef, useState } from "react";
 import type { FileAttachment, MentionChip } from "../utils/content";
@@ -69,7 +70,7 @@ export function AttachmentMenu({
     try {
       const attachments = await Promise.all(
         files.map(async (file) => {
-          const filePath = (file as globalThis.File & { path?: string }).path;
+          const filePath = getFilePath(file);
           if (filePath) {
             return { id: filePath, label: file.name } satisfies FileAttachment;
           }
diff --git a/apps/code/src/renderer/features/message-editor/tiptap/useTiptapEditor.ts b/apps/code/src/renderer/features/message-editor/tiptap/useTiptapEditor.ts
index a5752157a..db7a8f895 100644
--- a/apps/code/src/renderer/features/message-editor/tiptap/useTiptapEditor.ts
+++ b/apps/code/src/renderer/features/message-editor/tiptap/useTiptapEditor.ts
@@ -4,6 +4,7 @@ import { toast } from "@renderer/utils/toast";
 import { useSettingsStore } from "@stores/settingsStore";
 import type { EditorView } from "@tiptap/pm/view";
 import { useEditor } from "@tiptap/react";
+import { getFilePath } from "@utils/getFilePath";
 import type React from "react";
 import { useCallback, useEffect, useRef, useState } from "react";
 import { usePromptHistoryStore } from "../stores/promptHistoryStore";
@@ -270,8 +271,7 @@ export function useTiptapEditor(options: UseTiptapEditorOptions) {
           const newAttachments: FileAttachment[] = [];
           for (let i = 0; i < files.length; i++) {
             const file = files[i];
-            // In Electron, File objects have a 'path' property
-            const path = (file as unknown as { path?: string }).path;
+            const path = getFilePath(file);
             if (path) {
               newAttachments.push({ id: path, label: file.name });
             }
diff --git a/apps/code/src/renderer/features/sessions/components/SessionView.tsx b/apps/code/src/renderer/features/sessions/components/SessionView.tsx
index 5ce4716fc..b18f24631 100644
--- a/apps/code/src/renderer/features/sessions/components/SessionView.tsx
+++ b/apps/code/src/renderer/features/sessions/components/SessionView.tsx
@@ -20,6 +20,7 @@ import {
   isJsonRpcNotification,
   isJsonRpcResponse,
 } from "@shared/types/session-events";
+import { getFilePath } from "@utils/getFilePath";
 import { useCallback, useEffect, useMemo, useRef, useState } from "react";
 import { useHotkeys } from "react-hotkeys-hook";
 import { getSessionService } from "../service/service";
@@ -328,7 +329,7 @@ export function SessionView({
 
     for (let i = 0; i < files.length; i++) {
       const file = files[i];
-      const filePath = (file as File & { path?: string }).path;
+      const filePath = getFilePath(file);
       if (filePath) {
         editorRef.current?.addAttachment({
           id: filePath,
diff --git a/apps/code/src/renderer/features/task-detail/components/TaskInput.tsx b/apps/code/src/renderer/features/task-detail/components/TaskInput.tsx
index 10bacc8af..2f84abfb4 100644
--- a/apps/code/src/renderer/features/task-detail/components/TaskInput.tsx
+++ b/apps/code/src/renderer/features/task-detail/components/TaskInput.tsx
@@ -29,6 +29,7 @@ import { useAuthStore } from "@renderer/features/auth/stores/authStore";
 import { useTRPC } from "@renderer/trpc/client";
 import { useNavigationStore } from "@stores/navigationStore";
 import { useQuery } from "@tanstack/react-query";
+import { getFilePath } from "@utils/getFilePath";
 import { useCallback, useEffect, useMemo, useRef, useState } from "react";
 import { useHotkeys } from "react-hotkeys-hook";
 import { usePreviewConfig } from "../hooks/usePreviewConfig";
@@ -344,7 +345,7 @@ export function TaskInput({
 
     for (let i = 0; i < files.length; i++) {
       const file = files[i];
-      const filePath = (file as File & { path?: string }).path;
+      const filePath = getFilePath(file);
       if (filePath) {
         editorRef.current?.addAttachment({
           id: filePath,
diff --git a/apps/code/src/renderer/types/electron.d.ts b/apps/code/src/renderer/types/electron.d.ts
index 322a3631c..9e0418bc3 100644
--- a/apps/code/src/renderer/types/electron.d.ts
+++ b/apps/code/src/renderer/types/electron.d.ts
@@ -1,3 +1,11 @@
 import "@main/services/types";
 
 // No legacy IPC interfaces - all communication now uses tRPC
+
+declare global {
+  interface Window {
+    electronUtils?: {
+      getPathForFile: (file: File) => string;
+    };
+  }
+}
diff --git a/apps/code/src/renderer/utils/getFilePath.ts b/apps/code/src/renderer/utils/getFilePath.ts
new file mode 100644
index 000000000..63ae65636
--- /dev/null
+++ b/apps/code/src/renderer/utils/getFilePath.ts
@@ -0,0 +1,13 @@
+/**
+ * Get the filesystem path for a File from a drag-and-drop or file input event.
+ *
+ * In Electron 32+ with contextIsolation, File.path is empty. The preload
+ * script exposes webUtils.getPathForFile as window.electronUtils.getPathForFile
+ * to bridge this gap.
+ */
+export function getFilePath(file: File): string {
+  if (window.electronUtils?.getPathForFile) {
+    return window.electronUtils.getPathForFile(file);
+  }
+  return (file as File & { path?: string }).path ?? "";
+}