PostHog · tatoalo · Apr 7, 2026
diff --git a/apps/code/src/renderer/api/posthogClient.ts b/apps/code/src/renderer/api/posthogClient.ts
@@ -557,20 +557,25 @@ export class PostHogAPIClient {
   async runTaskInCloud(
     taskId: string,
     branch?: string | null,
-    resumeOptions?: { resumeFromRunId: string; pendingUserMessage: string },
-    sandboxEnvironmentId?: string,
+    options?: {
+      resumeFromRunId?: string;
+      pendingUserMessage?: string;
+      sandboxEnvironmentId?: string;
+    },
   ): Promise<Task> {
     const teamId = await this.getTeamId();
     const body: Record<string, unknown> = { mode: "interactive" };
     if (branch) {
       body.branch = branch;
     }
-    if (resumeOptions) {
-      body.resume_from_run_id = resumeOptions.resumeFromRunId;
-      body.pending_user_message = resumeOptions.pendingUserMessage;
+    if (options?.resumeFromRunId) {
+      body.resume_from_run_id = options.resumeFromRunId;
+    }
+    if (options?.pendingUserMessage) {
+      body.pending_user_message = options.pendingUserMessage;
     }
-    if (sandboxEnvironmentId) {
-      body.sandbox_environment_id = sandboxEnvironmentId;
+    if (options?.sandboxEnvironmentId) {
+      body.sandbox_environment_id = options.sandboxEnvironmentId;
     }
 
     const data = await this.api.post(

diff --git a/apps/code/src/renderer/features/message-editor/components/AttachmentMenu.test.tsx b/apps/code/src/renderer/features/message-editor/components/AttachmentMenu.test.tsx
@@ -0,0 +1,66 @@
+import { Theme } from "@radix-ui/themes";
+import { render, screen } from "@testing-library/react";
+import userEvent from "@testing-library/user-event";
+import { beforeEach, describe, expect, it, vi } from "vitest";
+
+const mockSelectFiles = vi.hoisted(() => vi.fn());
+
+vi.mock("@renderer/trpc/client", () => ({
+  trpcClient: {
+    os: {
+      selectFiles: {
+        query: mockSelectFiles,
+      },
+    },
+  },
+  useTRPC: () => ({
+    git: {
+      getGhStatus: {
+        queryOptions: () => ({}),
+      },
+    },
+  }),
+}));
+
+vi.mock("@tanstack/react-query", () => ({
+  useQuery: () => ({ data: undefined }),
+}));
+
+vi.mock("@renderer/utils/toast", () => ({
+  toast: {
+    error: vi.fn(),
+  },
+}));
+
+import { AttachmentMenu } from "./AttachmentMenu";
+
+describe("AttachmentMenu", () => {
+  beforeEach(() => {
+    vi.clearAllMocks();
+  });
+
+  it("adds attachments using absolute file paths from the OS picker", async () => {
+    const user = userEvent.setup();
+    const onAddAttachment = vi.fn();
+
+    mockSelectFiles.mockResolvedValue(["/tmp/demo/test.txt"]);
+
+    render(
+      <Theme>
+        <AttachmentMenu
+          onAddAttachment={onAddAttachment}
+          onInsertChip={vi.fn()}
+        />
+      </Theme>,
+    );
+
+    await user.click(screen.getByRole("button"));
+    await user.click(await screen.findByText("Add file"));
+
+    expect(mockSelectFiles).toHaveBeenCalledOnce();
+    expect(onAddAttachment).toHaveBeenCalledWith({
+      id: "/tmp/demo/test.txt",
+      label: "test.txt",
+    });
+  });
+});
diff --git a/apps/code/src/renderer/features/message-editor/components/AttachmentMenu.tsx b/apps/code/src/renderer/features/message-editor/components/AttachmentMenu.tsx
@@ -1,11 +1,13 @@
 import "./AttachmentMenu.css";
-import { Tooltip } from "@components/ui/Tooltip";
 import { File, GithubLogo, Paperclip } from "@phosphor-icons/react";
 import { IconButton, Popover } from "@radix-ui/themes";
-import { useTRPC } from "@renderer/trpc/client";
+import { trpcClient, useTRPC } from "@renderer/trpc/client";
+import { toast } from "@renderer/utils/toast";
 import { useQuery } from "@tanstack/react-query";
+import { getFileName } from "@utils/path";
 import { useRef, useState } from "react";
 import type { FileAttachment, MentionChip } from "../utils/content";
+import { persistBrowserFile } from "../utils/persistFile";
 import { IssuePicker } from "./IssuePicker";
 
 type View = "menu" | "issues";
@@ -54,20 +56,42 @@ export function AttachmentMenu({
 
   const issueDisabledReason = getIssueDisabledReason(ghStatus, repoPath);
 
-  const handleFileSelect = (e: React.ChangeEvent<HTMLInputElement>) => {
-    const files = e.target.files;
-    if (files && files.length > 0) {
-      const fileArray = Array.from(files);
-      for (const file of fileArray) {
-        const filePath =
-          (file as globalThis.File & { path?: string }).path || file.name;
-        onAddAttachment({ id: filePath, label: file.name });
-      }
-      onAttachFiles?.(fileArray);
-    }
+  const handleFileSelect = async (e: React.ChangeEvent<HTMLInputElement>) => {
+    const files = e.target.files ? Array.from(e.target.files) : [];
     if (fileInputRef.current) {
       fileInputRef.current.value = "";
     }
+
+    if (files.length === 0) {
+      return;
+    }
+
+    try {
+      const attachments = await Promise.all(
+        files.map(async (file) => {
+          const filePath = (file as globalThis.File & { path?: string }).path;
+          if (filePath) {
+            return { id: filePath, label: file.name } satisfies FileAttachment;
+          }
+
+          return await persistBrowserFile(file);
+        }),
+      );
+
+      for (const attachment of attachments) {
+        if (attachment) {
+          onAddAttachment(attachment);
+        }
+      }
+
+      onAttachFiles?.(files);
+    } catch (error) {
+      toast.error(
+        error instanceof Error
+          ? error.message
+          : "Unable to attach selected files from this picker",
+      );
+    }
   };
 
   const handleOpenChange = (isOpen: boolean) => {
@@ -77,8 +101,21 @@ export function AttachmentMenu({
     }
   };
 
-  const handleAddFile = () => {
+  const handleAddFile = async () => {
     setOpen(false);
+
+    try {
+      const filePaths = await trpcClient.os.selectFiles.query();
+      if (filePaths.length > 0) {
+        for (const filePath of filePaths) {
+          onAddAttachment({ id: filePath, label: getFileName(filePath) });
+        }
+      }
+      return;
+    } catch {
+      // Fall back to the input element for non-Electron environments.
+    }
+
     fileInputRef.current?.click();
   };
 
@@ -112,18 +149,17 @@ export function AttachmentMenu({
         style={{ display: "none" }}
       />
       <Popover.Root open={open} onOpenChange={handleOpenChange}>
-        <Tooltip content={attachTooltip}>
-          <Popover.Trigger>
-            <IconButton
-              size="1"
-              variant="ghost"
-              color="gray"
-              disabled={disabled}
-            >
-              <Paperclip size={iconSize} weight="bold" />
-            </IconButton>
-          </Popover.Trigger>
-        </Tooltip>
+        <Popover.Trigger>
+          <IconButton
+            size="1"
+            variant="ghost"
+            color="gray"
+            disabled={disabled}
+            title={attachTooltip}
+          >
+            <Paperclip size={iconSize} weight="bold" />
+          </IconButton>
+        </Popover.Trigger>
         <Popover.Content side="top" align="start" style={{ padding: 0 }}>
           {view === "menu" ? (
             <div className="attachment-menu">
@@ -138,9 +174,7 @@ export function AttachmentMenu({
                 <span>Add file</span>
               </button>
               {issueDisabledReason ? (
-                <Tooltip content={issueDisabledReason} side="right">
-                  <span>{issueButton}</span>
-                </Tooltip>
+                <span title={issueDisabledReason}>{issueButton}</span>
               ) : (
                 issueButton
               )}

diff --git a/apps/code/src/renderer/features/message-editor/tiptap/useDraftSync.test.tsx b/apps/code/src/renderer/features/message-editor/tiptap/useDraftSync.test.tsx
@@ -0,0 +1,63 @@
+import { act, render, screen } from "@testing-library/react";
+import { beforeEach, describe, expect, it, vi } from "vitest";
+
+vi.mock("@utils/electronStorage", () => ({
+  electronStorage: {
+    getItem: () => null,
+    setItem: () => {},
+    removeItem: () => {},
+  },
+}));
+
+import { useDraftStore } from "../stores/draftStore";
+import { useDraftSync } from "./useDraftSync";
+
+function DraftAttachmentsProbe({ sessionId }: { sessionId: string }) {
+  const { restoredAttachments } = useDraftSync(null, sessionId);
+  return (
+    <div>
+      {restoredAttachments.map((att) => att.label).join(",") || "empty"}
+    </div>
+  );
+}
+
+describe("useDraftSync", () => {
+  beforeEach(() => {
+    vi.clearAllMocks();
+    useDraftStore.setState((state) => ({
+      ...state,
+      drafts: {},
+      contexts: {},
+      commands: {},
+      focusRequested: {},
+      pendingContent: {},
+      _hasHydrated: true,
+    }));
+  });
+
+  it("clears restored attachments when a draft no longer has attachments", () => {
+    const { rerender } = render(
+      <DraftAttachmentsProbe sessionId="session-1" />,
+    );
+
+    act(() => {
+      useDraftStore.getState().actions.setDraft("session-1", {
+        segments: [{ type: "text", text: "hello" }],
+        attachments: [{ id: "/tmp/file.txt", label: "file.txt" }],
+      });
+    });
+
+    expect(screen.getByText("file.txt")).toBeInTheDocument();
+
+    act(() => {
+      useDraftStore.getState().actions.setDraft("session-1", {
+        segments: [{ type: "text", text: "hello" }],
+      });
+    });
+
+    expect(screen.getByText("empty")).toBeInTheDocument();
+
+    rerender(<DraftAttachmentsProbe sessionId="session-2" />);
+    expect(screen.getByText("empty")).toBeInTheDocument();
+  });
+});
diff --git a/apps/code/src/renderer/features/message-editor/tiptap/useDraftSync.ts b/apps/code/src/renderer/features/message-editor/tiptap/useDraftSync.ts
@@ -171,9 +171,12 @@ export function useDraftSync(
   >([]);
   useLayoutEffect(() => {
     if (!draft || typeof draft === "string") return;
-    if (draft.attachments && draft.attachments.length > 0) {
-      setRestoredAttachments(draft.attachments);
-    }
+    const incoming = draft.attachments ?? [];
+    // Short-circuit the common empty→empty case to avoid creating a new array
+    // reference that would trigger unnecessary re-renders.
+    setRestoredAttachments((prev) =>
+      prev.length === 0 && incoming.length === 0 ? prev : incoming,
+    );
   }, [draft]);
 
   const attachmentsRef = useRef<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
@@ -1,6 +1,5 @@
 import { sessionStoreSetters } from "@features/sessions/stores/sessionStore";
 import { useSettingsStore as useFeatureSettingsStore } from "@features/settings/stores/settingsStore";
-import { trpcClient } from "@renderer/trpc/client";
 import { toast } from "@renderer/utils/toast";
 import { useSettingsStore } from "@stores/settingsStore";
 import type { EditorView } from "@tiptap/pm/view";
@@ -10,6 +9,7 @@ import { useCallback, useEffect, useRef, useState } from "react";
 import { usePromptHistoryStore } from "../stores/promptHistoryStore";
 import type { FileAttachment, MentionChip } from "../utils/content";
 import { contentToXml, isContentEmpty } from "../utils/content";
+import { persistImageFile, persistTextContent } from "../utils/persistFile";
 import { getEditorExtensions } from "./extensions";
 import { type DraftContext, useDraftSync } from "./useDraftSync";
 
@@ -45,7 +45,7 @@ async function pasteTextAsFile(
   text: string,
   pasteCountRef: React.MutableRefObject<number>,
 ): Promise<void> {
-  const result = await trpcClient.os.saveClipboardText.mutate({ text });
+  const result = await persistTextContent(text);
   pasteCountRef.current += 1;
   const lineCount = text.split("\n").length;
   const label = `Pasted text #${pasteCountRef.current} (${lineCount} lines)`;
@@ -331,19 +331,7 @@ export function useTiptapEditor(options: UseTiptapEditorOptions) {
                 if (!file) continue;
 
                 try {
-                  const arrayBuffer = await file.arrayBuffer();
-                  const base64 = btoa(
-                    new Uint8Array(arrayBuffer).reduce(
-                      (data, byte) => data + String.fromCharCode(byte),
-                      "",
-                    ),
-                  );
-
-                  const result = await trpcClient.os.saveClipboardImage.mutate({
-                    base64Data: base64,
-                    mimeType: file.type,
-                    originalName: file.name,
-                  });
+                  const result = await persistImageFile(file);
 
                   setAttachments((prev) => {
                     if (prev.some((a) => a.id === result.path)) return prev;
@@ -448,9 +436,7 @@ export function useTiptapEditor(options: UseTiptapEditorOptions) {
 
   // Restore attachments from draft on mount
   useEffect(() => {
-    if (draft.restoredAttachments.length > 0) {
-      setAttachments(draft.restoredAttachments);
-    }
+    setAttachments(draft.restoredAttachments);
     // Only run on mount / session change
     // eslint-disable-next-line react-hooks/exhaustive-deps
   }, [draft.restoredAttachments]);

diff --git a/apps/code/src/renderer/features/sessions/components/ConversationView.tsx b/apps/code/src/renderer/features/sessions/components/ConversationView.tsx
@@ -146,6 +146,7 @@ export function ConversationView({
           return (
             <UserMessage
               content={item.content}
+              attachments={item.attachments}
               timestamp={item.timestamp}
               sourceUrl={
                 slackThreadUrl && item.id === firstUserMessageId