Q140: a message can carry several files, or files alone

Co-Authored-By: Claude Opus 5.5 <noreply@anthropic.com>

src/main/app/ipc-handlers.ts

@@ -340,9 +340,9 @@ export function registerIpcHandlers(deps: IpcDeps): void {
 
   handle("importFile", async (input) => {
     try {
-      const fileId = await files.importFile(input);
+      const imported = await files.importFile(input);
-      if (fileId) notifyDataChanged();
+      if (imported.fileIds.length > 0) notifyDataChanged();
-      return ok(fileId);
+      return ok(imported);
     } catch (error) {
       return fail("file_import_failed", error instanceof Error ? error.message : String(error));
     }

src/main/services/chat-service.ts

@@ -120,7 +120,7 @@ export class ChatService {
 
   sendMessage(input: SendMessageInput): string {
     const body = input.bodyMd.trim();
-    if (!body) throw new Error("Message body is required.");
+    if (!body && (input.attachmentFileIds ?? []).length === 0) throw new Error("A message needs text or a file.");
     const space = this.requireSpace(input.orgId, input.spaceId);
     const sender = this.requireSender(input.orgId, input.senderType, input.senderId);
     if (sender) this.requireMembership(space.id, sender);
@@ -160,7 +160,7 @@ export class ChatService {
       this.db.prepare(`
         insert into chat_threads(id, org_id, space_id, root_message_id, title, state, created_at, updated_at)
         values (?, ?, ?, ?, ?, ?, ?, ?)
-      `).run(threadId, input.orgId, input.spaceId, id, createThreadTitle(body), "open", now, now);
+      `).run(threadId, input.orgId, input.spaceId, id, createThreadTitle(body || this.fileNames(input.orgId, attachmentFileIds)), "open", now, now);
     } else {
       this.db.prepare("update chat_threads set updated_at = ? where id = ? and org_id = ?").run(now, input.threadId, input.orgId);
     }
@@ -426,6 +426,13 @@ export class ChatService {
     return thread;
   }
 
+  /** The attached files' names, in order, to title a thread whose first message is files alone. */
+  private fileNames(orgId: string, fileIds: string[]): string {
+    const names = this.db.prepare("select id, name from file_objects where org_id = ?").all(orgId) as Array<{ id: string; name: string }>;
+    const byId = new Map(names.map((file) => [file.id, file.name]));
+    return fileIds.map((fileId) => byId.get(fileId)!).join(", ");
+  }
+
   private requireAttachments(orgId: string, fileIds: string[], sender: PrincipalRef | null): FileHandoffAttachment[] {
     if (new Set(fileIds).size !== fileIds.length) throw new Error("Attachment file ids must be unique.");
     return fileIds.map((fileId) => {

src/main/services/file-service.ts

@@ -3,7 +3,7 @@ import { copyFile } from "node:fs/promises";
 import { basename, join } from "node:path";
 import type { DatabaseSync } from "node:sqlite";
 import { dialog, shell } from "electron";
-import type { ImportFileInput, OpenFileInput } from "../../shared/commands";
+import type { ImportedFiles, ImportFileInput, OpenFileInput } from "../../shared/commands";
 import { FILE_SCAN_STATE } from "../../shared/domain";
 import { createId } from "../../shared/ids";
 import { AuditService } from "./audit-service";
@@ -26,13 +26,24 @@ export class FileService {
     mkdirSync(this.artifactRoot, { recursive: true });
   }
 
-  async importFile(input: ImportFileInput): Promise<string | null> {
+  /** Imports every file the user picks, in order; one that fails is reported and does not undo or hide the others. */
+  async importFile(input: ImportFileInput): Promise<ImportedFiles> {
     const result = await dialog.showOpenDialog({
-      properties: ["openFile"],
+      properties: ["openFile", "multiSelections"],
       securityScopedBookmarks: true,
     });
-    if (result.canceled || result.filePaths.length === 0) return null;
+    const imported: ImportedFiles = { fileIds: [], failures: [] };
-    return this.importPath(input.orgId, result.filePaths[0], input.spaceId ?? null);
+    if (result.canceled) return imported;
+    for (const path of result.filePaths) {
+      try {
+        imported.fileIds.push(await this.importPath(input.orgId, path, input.spaceId ?? null));
+      } catch (error) {
+        const reason = error instanceof Error ? error.message : String(error);
+        console.warn(`[files] import of ${basename(path)} failed: ${reason}`);
+        imported.failures.push({ name: basename(path), reason });
+      }
+    }
+    return imported;
   }
 
   /** A file imported into a direct conversation or restricted channel is readable by that space's members only. */

src/renderer/src/i18n/zh.ts

@@ -37,6 +37,8 @@ export const zh: Record<string, string> = {
   "Waiting on you, or resumes on its own at {time}.": "等待你处理，或于 {time} 自动恢复。",
   "Waiting on you.": "等待你处理。",
   "Not sent: {reason}": "未发送：{reason}",
+  "Remove {name}": "移除 {name}",
+  "Not attached: {reason}": "未能附加：{reason}",
   "Resume": "恢复",
   "Missing this run": "本次运行缺少的能力",
   "Disconnect": "断开连接",
@@ -420,7 +422,6 @@ export const zh: Record<string, string> = {
   "Region": "区域",
   "Rejected": "已驳回",
   "Reload models": "重新加载模型",
-  "Remove attachment": "移除附件",
   "Reporting lines": "汇报关系",
   "Request ID": "请求 ID",
   "Request instructions": "请求指令",

src/renderer/src/pages/ChatPage.tsx

@@ -22,7 +22,7 @@ function value(form: FormData, key: string): string {
 }
 
 const IDLE_SEND: SendState = { pending: false, error: null };
-const EMPTY_DRAFT: Draft = { body: "", attachmentFileId: "" };
+const EMPTY_DRAFT: Draft = { body: "", attachmentFileIds: [] };
 
 export function ChatPage({ snapshot, actions }: PageProps) {
   const orgId = activeOrgId(snapshot);
@@ -72,6 +72,7 @@ export function ChatPage({ snapshot, actions }: PageProps) {
   const [createOpen, setCreateOpen] = useState(false);
   // Text and attachment are kept per conversation, so switching neither loses one nor carries the other along.
   const [drafts, setDrafts] = useState<Record<string, Draft>>({});
+  const [attachErrors, setAttachErrors] = useState<Record<string, string | null>>({});
   const updateDraft = useCallback((spaceId: string, change: Partial<Draft>) =>
     setDrafts((current) => ({ ...current, [spaceId]: { ...(current[spaceId] ?? EMPTY_DRAFT), ...change } })), []);
   const saveDraftBody = useCallback((spaceId: string, body: string) => updateDraft(spaceId, { body }), [updateDraft]);
@@ -119,9 +120,9 @@ export function ChatPage({ snapshot, actions }: PageProps) {
     event.preventDefault();
     if (!activeSpace || sends[activeSpace.id]?.pending) return;
     const spaceId = activeSpace.id;
-    const sentAttachment = (drafts[spaceId] ?? EMPTY_DRAFT).attachmentFileId;
+    const sentAttachments = (drafts[spaceId] ?? EMPTY_DRAFT).attachmentFileIds;
     const body = value(new FormData(event.currentTarget), "message");
-    if (!body) return;
+    if (!body && sentAttachments.length === 0) return;
     setSends((current) => ({ ...current, [spaceId]: { pending: true, error: null } }));
     // The draft and attachment stay until the message is saved, so a refused send loses nothing.
     actions.run(() => window.agentCompany.sendMessage({
@@ -131,14 +132,14 @@ export function ChatPage({ snapshot, actions }: PageProps) {
       senderType: "employee",
       senderId: employee.id,
       bodyMd: body,
-      attachmentFileIds: sentAttachment ? [sentAttachment] : [],
+      attachmentFileIds: sentAttachments,
     })).then(() => {
       // Clear this conversation's mounted composer directly; reset() could restore the sent text as its default.
       const node = composerRef.current;
       if (node?.form?.dataset.spaceId === spaceId) node.value = "";
       setDrafts((current) => {
-        const kept = (current[spaceId] ?? EMPTY_DRAFT).attachmentFileId;
+        const kept = (current[spaceId] ?? EMPTY_DRAFT).attachmentFileIds.filter((fileId) => !sentAttachments.includes(fileId));
-        return { ...current, [spaceId]: { body: "", attachmentFileId: kept === sentAttachment ? "" : kept } };
+        return { ...current, [spaceId]: { body: "", attachmentFileIds: kept } };
       });
       setSends((current) => ({ ...current, [spaceId]: { pending: false, error: null } }));
     }).catch((error: unknown) => {
@@ -198,8 +199,18 @@ export function ChatPage({ snapshot, actions }: PageProps) {
     if (!activeSpaceId) return;
     const spaceId = activeSpaceId;
     void window.agentCompany.importFile({ orgId, spaceId }).then((result) => {
-      if (!result.ok) throw new Error(result.error.message);
+      if (!result.ok) {
-      if (result.data) updateDraft(spaceId, { attachmentFileId: result.data });
+        setAttachErrors((current) => ({ ...current, [spaceId]: result.error.message }));
+        return;
+      }
+      const { fileIds, failures } = result.data;
+      setDrafts((current) => {
+        const draft = current[spaceId] ?? EMPTY_DRAFT;
+        const added = fileIds.filter((fileId) => !draft.attachmentFileIds.includes(fileId));
+        return { ...current, [spaceId]: { ...draft, attachmentFileIds: [...draft.attachmentFileIds, ...added] } };
+      });
+      const reason = failures.map((failure) => `${failure.name} (${failure.reason})`).join("; ");
+      setAttachErrors((current) => ({ ...current, [spaceId]: reason || null }));
     });
   };
 
@@ -231,10 +242,13 @@ export function ChatPage({ snapshot, actions }: PageProps) {
         files={files}
         context={{ employees, agents, readersByMessage }}
         draft={(activeSpaceId ? drafts[activeSpaceId] : undefined) ?? EMPTY_DRAFT}
+        attachError={(activeSpaceId ? attachErrors[activeSpaceId] : undefined) ?? null}
         onDraftLeave={saveDraftBody}
         currentEmployeeId={employee.id}
-        onAttachmentChange={(fileId) => {
+        onAttachmentRemove={(fileId) => {
-          if (activeSpaceId) updateDraft(activeSpaceId, { attachmentFileId: fileId });
+          if (!activeSpaceId) return;
+          const remaining = ((drafts[activeSpaceId] ?? EMPTY_DRAFT).attachmentFileIds).filter((id) => id !== fileId);
+          updateDraft(activeSpaceId, { attachmentFileIds: remaining });
         }}
         onAttach={attachFile}
         onApprove={(approvalId) => decideApproval(approvalId, "approved")}

src/renderer/src/pages/FilesPage.tsx

@@ -44,6 +44,7 @@ export function FilesPage({ snapshot, actions }: PageProps) {
   const upload = () => {
     void window.agentCompany.importFile({ orgId }).then((result) => {
       if (!result.ok) throw new Error(result.error.message);
+      if (result.data.failures.length > 0) throw new Error(result.data.failures.map((failure) => `${failure.name}: ${failure.reason}`).join("; "));
     });
   };
   const openFile = (file: FileObjectRecord) => {

src/renderer/src/pages/chat/ChatComposer.tsx

@@ -11,22 +11,23 @@ export interface SendState {
   error: string | null;
 }
 
-/** A conversation's unsent message: its text and the file picked to go with it. */
+/** A conversation's unsent message: its text and the files picked to go with it. */
 export interface Draft {
   body: string;
-  attachmentFileId: string;
+  attachmentFileIds: string[];
 }
 
 export function ChatComposer({
   disabled,
   send,
   draft,
+  attachError,
   spaceId,
   onLeave,
   files,
   agents,
   employees,
-  onAttachmentChange,
+  onAttachmentRemove,
   onAttach,
   onSubmit,
   composerRef,
@@ -34,13 +35,15 @@ export function ChatComposer({
   disabled: boolean;
   send: SendState;
   draft: Draft;
+  /** Why some picked files could not be attached, or null. */
+  attachError: string | null;
   spaceId: string | null;
   /** Called with the unsent text when the composer goes away, so the conversation keeps it; must be stable. */
   onLeave: (spaceId: string, body: string) => void;
   files: FileObjectRecord[];
   agents: AgentRecord[];
   employees: EmployeeRecord[];
-  onAttachmentChange: (next: string) => void;
+  onAttachmentRemove: (fileId: string) => void;
   onAttach: () => void;
   onSubmit: (event: FormEvent<HTMLFormElement>) => void;
   composerRef: MutableRefObject<HTMLTextAreaElement | null>;
@@ -48,7 +51,7 @@ export function ChatComposer({
   const [slashOpen, setSlashOpen] = useState(false);
   // While a send is in flight nothing may change the draft it will clear on success.
   const locked = disabled || send.pending;
-  const attachment = files.find((file) => file.id === draft.attachmentFileId) ?? null;
+  const attachments = draft.attachmentFileIds.map((fileId) => files.find((file) => file.id === fileId) ?? { id: fileId, name: fileId });
   const internalRef = useRef<HTMLTextAreaElement | null>(null);
   const ref = composerRef ?? internalRef;
   useEffect(() => {
@@ -89,27 +92,28 @@ export function ChatComposer({
         <div className="row" style={{ paddingTop: 6, borderTop: "1px solid var(--border-soft)", gap: 4 }}>
           <IconButton icon="attach" label={t("Attach file")} onClick={onAttach} disabled={locked} />
           <IconButton icon="sparkle" label={t("Commands")} onClick={() => setSlashOpen((open) => !open)} disabled={locked} />
-          {attachment && (
+          {attachments.map((attachment) => (
-            <span className="pill" style={{ maxWidth: 220 }}>
+            <span key={attachment.id} className="pill" style={{ maxWidth: 220 }}>
               <Icon name="file" size={14} />
               <span style={{ overflow: "hidden", textOverflow: "ellipsis", whiteSpace: "nowrap" }}>{attachment.name}</span>
               <button
                 type="button"
-                aria-label={t("Remove attachment")}
+                aria-label={t("Remove {name}", { name: attachment.name })}
                 disabled={locked}
-                onClick={() => onAttachmentChange("")}
+                onClick={() => onAttachmentRemove(attachment.id)}
                 style={{ display: "inline-flex", border: 0, background: "transparent", padding: 0, color: "var(--text-3)", cursor: "pointer" }}
               >
                 <Icon name="x" size={14} />
               </button>
             </span>
-          )}
+          ))}
           <div style={{ marginLeft: "auto", display: "flex", alignItems: "center", gap: 6 }}>
             <span className="mono" style={{ fontSize: 12, color: "var(--text-3)" }}>Ctrl+Enter</span>
             <Button tone="primary" size="small" type="submit" disabled={locked}><Icon name="send" size={12} /> {t("Send")}</Button>
           </div>
         </div>
         {send.error && <div className="form-error" role="alert">{t("Not sent: {reason}", { reason: send.error })}</div>}
+        {attachError && <div className="form-error" role="alert">{t("Not attached: {reason}", { reason: attachError })}</div>}
         {slashOpen && !locked && (
           <div style={{ marginTop: 8, display: "flex", flexWrap: "wrap", gap: 6 }}>
             {SLASH_COMMANDS.map((command) => (

src/renderer/src/pages/chat/ChatConversation.tsx

@@ -25,9 +25,10 @@ export function ChatConversation({
   files,
   context,
   draft,
+  attachError,
   onDraftLeave,
   currentEmployeeId,
-  onAttachmentChange,
+  onAttachmentRemove,
   onAttach,
   onApprove,
   onDecline,
@@ -48,9 +49,10 @@ export function ChatConversation({
   files: FileObjectRecord[];
   context: MessageContext;
   draft: Draft;
+  attachError: string | null;
   onDraftLeave: (spaceId: string, body: string) => void;
   currentEmployeeId: string;
-  onAttachmentChange: (next: string) => void;
+  onAttachmentRemove: (fileId: string) => void;
   onAttach: () => void;
   onApprove: (approvalId: string) => void;
   onDecline: (approvalId: string) => void;
@@ -144,9 +146,10 @@ export function ChatConversation({
         agents={context.agents}
         employees={context.employees}
         draft={draft}
+        attachError={attachError}
         spaceId={space?.id ?? null}
         onLeave={onDraftLeave}
-        onAttachmentChange={onAttachmentChange}
+        onAttachmentRemove={onAttachmentRemove}
         onAttach={onAttach}
         onSubmit={onSubmit}
         composerRef={composerRef}

src/shared/commands/files.ts

@@ -1,3 +1,9 @@
+/** What a pick imported, in order, and each picked file that could not be imported, with why. */
+export interface ImportedFiles {
+  fileIds: string[];
+  failures: Array<{ name: string; reason: string }>;
+}
+
 export interface ImportFileInput {
   orgId: string;
   /** The conversation the file is attached in; a direct or restricted one keeps the file to its members. */

src/shared/desktop-api.ts

@@ -58,6 +58,7 @@ import type {
   DeleteMessageInput,
   DeleteOrganizationInput,
   EditMessageInput,
+  ImportedFiles,
   ImportFileInput,
   OpenFileInput,
   GrantRoleInput,
@@ -174,7 +175,7 @@ export interface DesktopApi {
   launchSocialLogin(input: LaunchSocialLoginInput): Promise<DesktopResult<null>>;
   createScheduledPost(input: CreateScheduledPostInput): Promise<DesktopResult<AppSnapshot>>;
   setScheduledPostState(input: SetScheduledPostStateInput): Promise<DesktopResult<AppSnapshot>>;
-  importFile(input: ImportFileInput): Promise<DesktopResult<string | null>>;
+  importFile(input: ImportFileInput): Promise<DesktopResult<ImportedFiles>>;
   openFile(input: OpenFileInput): Promise<DesktopResult<null>>;
   pickDirectory(): Promise<DesktopResult<string | null>>;
   setFilePinned(input: SetFilePinnedInput): Promise<DesktopResult<AppSnapshot>>;

tests/unit/chat-file-only.test.ts

@@ -0,0 +1,46 @@
+import { randomUUID } from "node:crypto";
+import { mkdirSync, writeFileSync } from "node:fs";
+import { tmpdir } from "node:os";
+import { join } from "node:path";
+import { describe, expect, test, vi } from "vitest";
+
+const picked: { paths: string[] } = { paths: [] };
+vi.mock("electron", () => ({ dialog: { showOpenDialog: async () => ({ canceled: false, filePaths: picked.paths }) }, shell: {} }));
+
+const { DatabaseConnection } = await import("../../src/main/database/connection");
+const { OrganizationService } = await import("../../src/main/services/organization-service");
+const { ChatService } = await import("../../src/main/services/chat-service");
+const { FileService } = await import("../../src/main/services/file-service");
+
+describe("delivering files in chat", () => {
+  test("several files go in one message, and a message may be files alone", async () => {
+    const connection = new DatabaseConnection(join(tmpdir(), `ac-file-only-${randomUUID()}.db`));
+    const chat = new ChatService(connection.db);
+    let orgId = "";
+    connection.transaction(() => {
+      orgId = new OrganizationService(connection.db).createOrganization({ organizationName: "Acme", employeeName: "Yang", mission: "m", goal: "g" });
+    });
+    const employeeId = (connection.db.prepare("select id from employees where org_id = ?").get(orgId) as { id: string }).id;
+    const spaceId = (connection.db.prepare("select id from chat_spaces where org_id = ? and name = 'general'").get(orgId) as { id: string }).id;
+    const source = join(tmpdir(), `ac-file-only-src-${randomUUID()}`);
+    mkdirSync(source, { recursive: true });
+    writeFileSync(join(source, "spec.md"), "The spec.");
+    writeFileSync(join(source, "plan.md"), "The plan.");
+    picked.paths = [join(source, "spec.md"), join(source, "missing.md"), join(source, "plan.md")];
+    const imported = await new FileService(connection.db, join(tmpdir(), `ac-file-only-art-${randomUUID()}`)).importFile({ orgId, spaceId });
+    // A file that cannot be imported is reported by name and does not drop the others.
+    expect(imported.fileIds).toHaveLength(2);
+    expect(imported.failures.map((failure) => failure.name)).toEqual(["missing.md"]);
+    const fileIds = imported.fileIds;
+
+    const send = (bodyMd: string, attachmentFileIds: string[]) => connection.transaction(() => chat.sendMessage({
+      orgId, spaceId, threadId: null, senderType: "employee", senderId: employeeId, bodyMd, attachmentFileIds,
+    }));
+    const messageId = send("  ", fileIds);
+    expect(connection.db.prepare("select count(*) as n from chat_attachments where message_id = ?").get(messageId)).toEqual({ n: 2 });
+    expect(connection.db.prepare("select t.title from chat_threads t join chat_messages m on m.thread_id = t.id where m.id = ?").get(messageId))
+      .toEqual({ title: "spec.md, plan.md" });
+    expect(() => send("  ", [])).toThrow("A message needs text or a file.");
+    connection.close();
+  });
+});