diff --git a/AgentCompany-New/src/main/app/ipc-handlers.ts b/AgentCompany-New/src/main/app/ipc-handlers.ts
index 7f2f9a6e..ffaff708 100644
--- a/AgentCompany-New/src/main/app/ipc-handlers.ts
+++ b/AgentCompany-New/src/main/app/ipc-handlers.ts
@@ -188,9 +188,9 @@ export function registerIpcHandlers(deps: IpcDeps): void {
 
   ipcMain.handle(IPC_CHANNELS.importFile, async (_event, input) => {
     try {
-      await files.importFile(input);
-      deps.mainWindow.webContents.send(IPC_CHANNELS.rendererEvent, { type: "snapshot-changed" });
-      return ok(snapshot.load());
+      const fileId = await files.importFile(input);
+      if (fileId) deps.mainWindow.webContents.send(IPC_CHANNELS.rendererEvent, { type: "snapshot-changed" });
+      return ok(fileId);
     } catch (error) {
       return fail("file_import_failed", error instanceof Error ? error.message : String(error));
     }
diff --git a/AgentCompany-New/src/renderer/src/pages/ChatPage.tsx b/AgentCompany-New/src/renderer/src/pages/ChatPage.tsx
index 686416c5..7e045bc2 100644
--- a/AgentCompany-New/src/renderer/src/pages/ChatPage.tsx
+++ b/AgentCompany-New/src/renderer/src/pages/ChatPage.tsx
@@ -224,6 +224,13 @@ export function ChatPage({ snapshot, actions }: PageProps) {
       actorId: employee.id,
     }));
 
+  const attachFile = () => {
+    void window.agentCompany.importFile({ orgId }).then((result) => {
+      if (!result.ok) throw new Error(result.error.message);
+      if (result.data) setAttachmentFileId(result.data);
+    });
+  };
+
   return (
     <div className="split-main">
       <ChatSidebar
@@ -255,6 +262,7 @@ export function ChatPage({ snapshot, actions }: PageProps) {
         attachmentFileId={attachmentFileId}
         currentEmployeeId={employee.id}
         onAttachmentChange={setAttachmentFileId}
+        onAttach={attachFile}
         onOpenThread={setOpenThreadId}
         onApprove={(approvalId) => decideApproval(approvalId, "approved")}
         onDecline={(approvalId) => decideApproval(approvalId, "declined")}
diff --git a/AgentCompany-New/src/renderer/src/pages/FilesPage.tsx b/AgentCompany-New/src/renderer/src/pages/FilesPage.tsx
index 3c2ded6c..576a4bf2 100644
--- a/AgentCompany-New/src/renderer/src/pages/FilesPage.tsx
+++ b/AgentCompany-New/src/renderer/src/pages/FilesPage.tsx
@@ -35,6 +35,12 @@ export function FilesPage({ snapshot, actions }: PageProps) {
   const pinnedFiles = files.filter((file) => file.pinned);
   const totalBytes = visibleFiles.reduce((sum, file) => sum + file.sizeBytes, 0);
 
+  const upload = () => {
+    void window.agentCompany.importFile({ orgId }).then((result) => {
+      if (!result.ok) throw new Error(result.error.message);
+    });
+  };
+
   return (
     <div style={{ display: "grid", gridTemplateColumns: "minmax(160px, 200px) minmax(0, 1fr)", gap: 24, height: "100%", minHeight: 0, padding: "28px 32px 0" }}>
       <FilesTree
@@ -57,7 +63,7 @@ export function FilesPage({ snapshot, actions }: PageProps) {
               { id: "list", label: "List" },
             ]}
           />
-          <Button tone="primary" onClick={() => void actions.run(() => window.agentCompany.importFile({ orgId }))}>
+          <Button tone="primary" onClick={upload}>
             <Icon name="upload" size={13} /> Upload
           </Button>
         </TopbarActions>
diff --git a/AgentCompany-New/src/renderer/src/pages/chat/ChatComposer.tsx b/AgentCompany-New/src/renderer/src/pages/chat/ChatComposer.tsx
index f0c4a78e..158a0834 100644
--- a/AgentCompany-New/src/renderer/src/pages/chat/ChatComposer.tsx
+++ b/AgentCompany-New/src/renderer/src/pages/chat/ChatComposer.tsx
@@ -8,6 +8,7 @@ export function ChatComposer({
   files,
   attachmentFileId,
   onAttachmentChange,
+  onAttach,
   onSubmit,
   composerRef,
 }: {
@@ -15,10 +16,12 @@ export function ChatComposer({
   files: FileObjectRecord[];
   attachmentFileId: string;
   onAttachmentChange: (next: string) => void;
+  onAttach: () => void;
   onSubmit: (event: FormEvent<HTMLFormElement>) => void;
   composerRef: MutableRefObject<HTMLTextAreaElement | null>;
 }) {
   const [slashOpen, setSlashOpen] = useState(false);
+  const attachment = files.find((file) => file.id === attachmentFileId) ?? null;
 
   const insert = (text: string) => {
     const node = composerRef.current;
@@ -61,19 +64,22 @@ export function ChatComposer({
           }}
         />
         <div className="row" style={{ paddingTop: 6, borderTop: "1px solid var(--border-soft)", gap: 4 }}>
-          <IconButton icon="attach" label="Attach" />
-          <select
-            className="input"
-            value={attachmentFileId}
-            onChange={(event) => onAttachmentChange(event.target.value)}
-            aria-label="File attachment"
-            style={{ maxWidth: 180, padding: "4px 8px", height: 28, fontSize: 12 }}
-            disabled={disabled}
-          >
-            <option value="">No attachment</option>
-            {files.map((file) => <option key={file.id} value={file.id}>{file.name}</option>)}
-          </select>
+          <IconButton icon="attach" label="Attach file" onClick={onAttach} disabled={disabled} />
           <IconButton icon="sparkle" label="Commands" onClick={() => setSlashOpen((open) => !open)} />
+          {attachment && (
+            <span className="pill" style={{ maxWidth: 220 }}>
+              <Icon name="file" size={11} />
+              <span style={{ overflow: "hidden", textOverflow: "ellipsis", whiteSpace: "nowrap" }}>{attachment.name}</span>
+              <button
+                type="button"
+                aria-label="Remove attachment"
+                onClick={() => onAttachmentChange("")}
+                style={{ display: "inline-flex", border: 0, background: "transparent", padding: 0, color: "var(--text-3)", cursor: "pointer" }}
+              >
+                <Icon name="x" size={11} />
+              </button>
+            </span>
+          )}
           <div style={{ marginLeft: "auto", display: "flex", alignItems: "center", gap: 6 }}>
             <span className="mono" style={{ fontSize: 11, color: "var(--text-3)" }}>⌘↵</span>
             <Button tone="primary" size="small" type="submit" disabled={disabled}><Icon name="send" size={12} /> Send</Button>
diff --git a/AgentCompany-New/src/renderer/src/pages/chat/ChatConversation.tsx b/AgentCompany-New/src/renderer/src/pages/chat/ChatConversation.tsx
index c704cf2a..f2007f1d 100644
--- a/AgentCompany-New/src/renderer/src/pages/chat/ChatConversation.tsx
+++ b/AgentCompany-New/src/renderer/src/pages/chat/ChatConversation.tsx
@@ -29,6 +29,7 @@ export function ChatConversation({
   attachmentFileId,
   currentEmployeeId,
   onAttachmentChange,
+  onAttach,
   onOpenThread,
   onApprove,
   onDecline,
@@ -51,6 +52,7 @@ export function ChatConversation({
   attachmentFileId: string;
   currentEmployeeId: string;
   onAttachmentChange: (next: string) => void;
+  onAttach: () => void;
   onOpenThread: (threadId: string) => void;
   onApprove: (approvalId: string) => void;
   onDecline: (approvalId: string) => void;
@@ -93,6 +95,7 @@ export function ChatConversation({
         files={files}
         attachmentFileId={attachmentFileId}
         onAttachmentChange={onAttachmentChange}
+        onAttach={onAttach}
         onSubmit={onSubmit}
         composerRef={composerRef}
       />
diff --git a/AgentCompany-New/src/shared/desktop-api.ts b/AgentCompany-New/src/shared/desktop-api.ts
index 15304897..87055859 100644
--- a/AgentCompany-New/src/shared/desktop-api.ts
+++ b/AgentCompany-New/src/shared/desktop-api.ts
@@ -96,7 +96,7 @@ 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<AppSnapshot>>;
+  importFile(input: ImportFileInput): Promise<DesktopResult<string | null>>;
   pickDirectory(): Promise<DesktopResult<string | null>>;
   setFilePinned(input: SetFilePinnedInput): Promise<DesktopResult<AppSnapshot>>;
   createMigrationReport(input: CreateMigrationReportInput): Promise<DesktopResult<AppSnapshot>>;