diff --git a/.changeset/attachment-sending-indicator.md b/.changeset/attachment-sending-indicator.md
index 3c7eab7..4c033b1 100644
--- a/.changeset/attachment-sending-indicator.md
+++ b/.changeset/attachment-sending-indicator.md
@@ -2,4 +2,4 @@
 "@jmfederico/pi-web": patch
 ---
 
-Show a sending indicator in the chat composer while messages with image attachments are uploading. Previously the composer cleared instantly while the upload, server-side image resizing, and first-session open happened in the background, so it looked like nothing was happening. The Send button now shows "Sending…" and a "Sending your files…" (or "Saving your files…" for folder mode) hint until the message lands, and the composer is disabled while in flight.
+Show a sending indicator in the chat while messages with image attachments are uploading. Previously the composer cleared instantly while the upload, server-side image resizing, and first-session open happened in the background, so it looked like nothing was happening. The existing chat activity dock now shows "Sending your message…" during that window (including the folder-mode upload step) and is superseded by the real session activity once the message lands. Attachment sending is now orchestrated in the session controller so there is a single, consistent indicator.
diff --git a/src/client/src/appState.ts b/src/client/src/appState.ts
index 9a79f4c..06c4e67 100644
--- a/src/client/src/appState.ts
+++ b/src/client/src/appState.ts
@@ -17,6 +17,7 @@ export interface AppState {
   messagePageTotal: number;
   isLoadingEarlierMessages: boolean;
   isReceivingPartialStream: boolean;
+  isSendingPrompt: boolean;
   isLoadingProjects: boolean;
   isLoadingWorkspaces: boolean;
   selectedProject: Project | undefined;
@@ -113,6 +114,7 @@ export function initialAppState(): AppState {
     messagePageTotal: 0,
     isLoadingEarlierMessages: false,
     isReceivingPartialStream: false,
+    isSendingPrompt: false,
     isLoadingProjects: false,
     isLoadingWorkspaces: false,
     selectedProject: undefined,
diff --git a/src/client/src/components/ChatView.ts b/src/client/src/components/ChatView.ts
index 89cb3bc..e81573a 100644
--- a/src/client/src/components/ChatView.ts
+++ b/src/client/src/components/ChatView.ts
@@ -48,6 +48,7 @@ export class ChatView extends LitElement {
   @property({ type: Boolean }) hasMore = false;
   @property({ type: Boolean }) loadingMore = false;
   @property({ type: Boolean }) isReceivingPartialStream = false;
+  @property({ type: Boolean }) isSendingPrompt = false;
   @property({ type: Boolean }) isCompacting = false;
   @property({ type: Number }) pendingMessageCount = 0;
   @property({ attribute: false }) status?: SessionStatus;
@@ -191,13 +192,22 @@ export class ChatView extends LitElement {
   }
 
   private isSessionLive(): boolean {
-    return this.status?.isStreaming === true
+    return this.isSendingPrompt
+      || this.status?.isStreaming === true
       || this.status?.isCompacting === true
       || this.status?.isBashRunning === true
       || this.activity?.phase === "active";
   }
 
   private renderActivityDock() {
+    if (this.isSendingPrompt) {
+      return html`
+        <div class="activity-dock active" aria-live="polite">
+          <span class="dot"></span>
+          <span class="activity-text">Sending your message…</span>
+        </div>
+      `;
+    }
     const state = this.activityState();
     if (state === undefined) return null;
     const active = state !== "idle" || this.activity?.phase === "active";
diff --git a/src/client/src/components/PiWebApp.ts b/src/client/src/components/PiWebApp.ts
index 531a89f..3b16bb4 100644
--- a/src/client/src/components/PiWebApp.ts
+++ b/src/client/src/components/PiWebApp.ts
@@ -1664,10 +1664,10 @@ export class PiWebApp extends LitElement {
     if (isThinkingLevel(value)) await this.sessions.setThinkingLevel(value);
   }
 
-  private async sendPrompt(text: string, streamingBehavior?: "steer" | "followUp", attachments?: import("../api").PromptAttachment[]): Promise<void> {
+  private sendPrompt(text: string, streamingBehavior?: "steer" | "followUp", attachments?: import("../api").PromptAttachment[], delivery?: import("../../../shared/apiTypes").PromptAttachmentDelivery): void {
     const hasAttachments = attachments !== undefined && attachments.length > 0;
     if (!hasAttachments && streamingBehavior === undefined && this.auth.handleSlashCommand(text)) return;
-    await this.sessions.send(text, streamingBehavior, attachments);
+    void this.sessions.send(text, streamingBehavior, attachments, delivery);
   }
 
   private renderContextBar() {
@@ -1728,8 +1728,8 @@ export class PiWebApp extends LitElement {
           ${state.error ? html`<div class="error">${state.error}</div>` : null}
           <div class="mobile-navigation-panel">${this.appShell.isMobileNavigationLayout ? this.renderNavigationPanel() : null}</div>
           ${state.selectedSession ? html`
-            <chat-view .sessionId=${state.selectedSession.id} .messages=${state.messages} .messageStart=${state.messagePageStart} .messageEnd=${state.messagePageEnd} .messageTotal=${state.messagePageTotal} .hasMore=${state.messagePageStart > 0} .loadingMore=${state.isLoadingEarlierMessages} .isReceivingPartialStream=${state.isReceivingPartialStream} .isCompacting=${state.status?.isCompacting === true} .pendingMessageCount=${state.status?.pendingMessageCount ?? 0} .status=${state.status} .activity=${state.activity} .onLoadMore=${() => this.withChatPrependTransition(() => this.sessions.loadEarlierMessages())}></chat-view>
-            <prompt-editor .sessionId=${state.selectedSession.id} .cwd=${state.selectedWorkspace?.path} .machineId=${selectedMachineId(state)} .disabled=${state.selectedSession.archived === true} .canSteer=${state.status?.isStreaming === true} .isCompacting=${state.status?.isCompacting === true} .canStop=${state.status?.isStreaming === true || state.status?.isBashRunning === true || state.status?.isCompacting === true || (state.status?.pendingMessageCount ?? 0) > 0} .status=${state.status} .onSend=${(text: string, streamingBehavior?: "steer" | "followUp", attachments?: import("../api").PromptAttachment[]) => this.sendPrompt(text, streamingBehavior, attachments)} .onSaveAttachments=${(attachments: import("../api").PromptAttachment[]) => this.sessions.saveAttachments(attachments)} .onStop=${() => this.sessions.stopActiveWork()} .onSelectModel=${() => { void this.openModelDialog(); }} .onSelectThinking=${() => { void this.openThinkingDialog(); }}></prompt-editor>
+            <chat-view .sessionId=${state.selectedSession.id} .messages=${state.messages} .messageStart=${state.messagePageStart} .messageEnd=${state.messagePageEnd} .messageTotal=${state.messagePageTotal} .hasMore=${state.messagePageStart > 0} .loadingMore=${state.isLoadingEarlierMessages} .isReceivingPartialStream=${state.isReceivingPartialStream} .isSendingPrompt=${state.isSendingPrompt} .isCompacting=${state.status?.isCompacting === true} .pendingMessageCount=${state.status?.pendingMessageCount ?? 0} .status=${state.status} .activity=${state.activity} .onLoadMore=${() => this.withChatPrependTransition(() => this.sessions.loadEarlierMessages())}></chat-view>
+            <prompt-editor .sessionId=${state.selectedSession.id} .cwd=${state.selectedWorkspace?.path} .machineId=${selectedMachineId(state)} .disabled=${state.selectedSession.archived === true} .canSteer=${state.status?.isStreaming === true} .isCompacting=${state.status?.isCompacting === true} .canStop=${state.status?.isStreaming === true || state.status?.isBashRunning === true || state.status?.isCompacting === true || (state.status?.pendingMessageCount ?? 0) > 0} .status=${state.status} .sending=${state.isSendingPrompt} .onSend=${(text: string, streamingBehavior?: "steer" | "followUp", attachments?: import("../api").PromptAttachment[], delivery?: import("../../../shared/apiTypes").PromptAttachmentDelivery) => { this.sendPrompt(text, streamingBehavior, attachments, delivery); }} .onStop=${() => this.sessions.stopActiveWork()} .onSelectModel=${() => { void this.openModelDialog(); }} .onSelectThinking=${() => { void this.openThinkingDialog(); }}></prompt-editor>
             <status-bar .status=${state.status}></status-bar>
             ${state.commandDialog !== undefined ? html`<command-picker .title=${state.commandDialog.title} .options=${state.commandDialog.options} .onPick=${(value: string) => this.sessions.respondToCommand(state.commandDialog?.requestId ?? "", value)} .onCancel=${() => { this.sessions.cancelCommand(); }}></command-picker>` : null}
             ${state.modelDialog !== undefined ? html`<command-picker title=${state.modelDialog.title} .searchable=${true} .options=${state.modelDialog.options} .selectedValue=${state.modelDialog.selectedValue} .onPick=${(value: string) => { void this.pickModel(value); }} .onCancel=${() => { this.setState({ modelDialog: undefined }); }}></command-picker>` : null}
diff --git a/src/client/src/components/PromptEditor.ts b/src/client/src/components/PromptEditor.ts
index 11c3594..2e6312d 100644
--- a/src/client/src/components/PromptEditor.ts
+++ b/src/client/src/components/PromptEditor.ts
@@ -35,8 +35,8 @@ export class PromptEditor extends LitElement {
   @property({ type: Boolean }) isCompacting = false;
   @property({ type: Boolean }) canStop = false;
   @property({ attribute: false }) status?: SessionStatus;
-  @property({ attribute: false }) onSend?: (text: string, streamingBehavior?: "steer" | "followUp", attachments?: PromptAttachment[]) => void | Promise<void>;
-  @property({ attribute: false }) onSaveAttachments?: (attachments: PromptAttachment[]) => Promise<{ path: string }[]>;
+  @property({ type: Boolean }) sending = false;
+  @property({ attribute: false }) onSend?: (text: string, streamingBehavior?: "steer" | "followUp", attachments?: PromptAttachment[], delivery?: PromptAttachmentDelivery) => void | Promise<void>;
   @property({ attribute: false }) onStop?: () => void;
   @property({ attribute: false }) onSelectModel?: () => void;
   @property({ attribute: false }) onSelectThinking?: () => void;
@@ -48,8 +48,6 @@ export class PromptEditor extends LitElement {
   @state() private attachments: PendingAttachment[] = [];
   @state() private attachmentDelivery: PromptAttachmentDelivery = loadAttachmentDelivery();
   @state() private attachmentError: string | undefined = undefined;
-  @state() private isSavingAttachments = false;
-  @state() private isSending = false;
   private attachmentSeq = 0;
   private requestVersion = 0;
   private editor: EditorView | undefined;
@@ -87,16 +85,13 @@ export class PromptEditor extends LitElement {
     const inputMode = inputModeForDraft(this.draft);
     const shellMode = inputMode.kind === "shell";
     const queuesInput = this.canSteer || this.isCompacting;
-    const uploading = this.isSavingAttachments || this.isSending;
-    const busy = this.disabled || uploading;
-    const sendLabel = uploading ? "Sending…" : queuesInput ? "Queue" : "Send";
+    const busy = this.disabled || this.sending;
     return html`
       <footer class=${shellMode ? "shell-mode" : ""} @paste=${(event: ClipboardEvent) => { void this.handlePaste(event); }} @dragover=${(event: DragEvent) => { this.handleDragOver(event); }} @drop=${(event: DragEvent) => { void this.handleDrop(event); }}>
         <div class="editor-wrap">
           <div class=${`markdown-editor${this.disabled ? " markdown-editor-disabled" : ""}`} aria-label="Message pi" aria-disabled=${this.disabled ? "true" : "false"}></div>
           ${shellMode ? html`<div class="mode-hint">Shell command${inputMode.excludeFromContext ? " · excluded from context" : ""}</div>` : null}
           ${this.isCompacting && !shellMode ? html`<div class="mode-hint">Compacting history · message will be queued</div>` : null}
-          ${uploading ? html`<div class="mode-hint sending-hint" role="status">${this.isSavingAttachments ? "Saving your files…" : "Sending your files…"}</div>` : null}
           ${this.renderAttachments()}
           <autocomplete-menu .items=${this.completions} .selectedIndex=${this.selectedIndex} .onPick=${(item: CompletionItem) => { this.pick(item); }}></autocomplete-menu>
         </div>
@@ -104,8 +99,8 @@ export class PromptEditor extends LitElement {
           ${this.renderCompactStatus()}
           <input class="attachment-input" type="file" accept="image/png,image/jpeg,image/gif,image/webp" multiple hidden @change=${(event: Event) => { void this.handleFileInput(event); }} />
           <button class="attach-button" ?disabled=${busy} title="Attach images" @click=${() => { this.attachmentInput?.click(); }}>Attach</button>
-          <button ?disabled=${busy} title=${queuesInput ? "Queue until the current activity finishes" : "Send message"} @click=${() => { void this.send("followUp"); }}>${sendLabel}</button>
-          ${this.canSteer && !this.isCompacting ? html`<button ?disabled=${busy} title="Steer the current response before the next model call" @click=${() => { void this.send("steer"); }}>Steer</button>` : null}
+          <button ?disabled=${busy} title=${queuesInput ? "Queue until the current activity finishes" : "Send message"} @click=${() => { this.send("followUp"); }}>${queuesInput ? "Queue" : "Send"}</button>
+          ${this.canSteer && !this.isCompacting ? html`<button ?disabled=${busy} title="Steer the current response before the next model call" @click=${() => { this.send("steer"); }}>Steer</button>` : null}
           <button ?disabled=${this.disabled || !this.canStop} title=${this.canStop ? "Stop current work and clear queued messages" : "Nothing running"} @click=${() => this.onStop?.()}>Stop</button>
         </div>
       </footer>
@@ -348,7 +343,7 @@ export class PromptEditor extends LitElement {
       if (completion !== undefined) this.pick(completion);
       return true;
     }
-    void this.send(this.canSteer || this.isCompacting ? "followUp" : undefined);
+    this.send(this.canSteer || this.isCompacting ? "followUp" : undefined);
     return true;
   }
 
@@ -380,52 +375,19 @@ export class PromptEditor extends LitElement {
     this.completions = [];
   }
 
-  private async send(streamingBehavior?: "steer" | "followUp") {
-    if (this.disabled || this.isSavingAttachments || this.isSending) return;
+  private send(streamingBehavior?: "steer" | "followUp") {
+    if (this.disabled || this.sending) return;
     const text = this.draft.trim();
     const pending = this.attachments;
     if (text === "" && pending.length === 0) return;
     const behavior = this.canSteer || this.isCompacting ? streamingBehavior : undefined;
-
-    if (pending.length > 0 && this.attachmentDelivery === "folder") {
-      await this.sendWithFolderAttachments(text, behavior);
-      return;
-    }
-
     const attachments = pending.length > 0 ? this.currentAttachments() : undefined;
+    const delivery = this.attachmentDelivery;
     this.resetComposer();
-    if (attachments === undefined) {
-      // Plain text messages stay fire-and-forget so the input frees up instantly.
-      void this.onSend?.(text, behavior, attachments);
-      return;
-    }
-    // Image uploads can take a moment (large payloads, server-side resizing,
-    // first-session open), so surface a sending indicator until they land.
-    this.isSending = true;
-    try {
-      await this.onSend?.(text, behavior, attachments);
-    } catch (error) {
-      this.attachmentError = error instanceof Error ? error.message : String(error);
-    } finally {
-      this.isSending = false;
-    }
-  }
-
-  private async sendWithFolderAttachments(text: string, behavior?: "steer" | "followUp") {
-    if (this.onSaveAttachments === undefined) return;
-    this.isSavingAttachments = true;
-    this.attachmentError = undefined;
-    try {
-      const saved = await this.onSaveAttachments(this.currentAttachments());
-      const references = saved.map((file) => fileCompletionInsertText(file.path, false)).join(" ");
-      const body = text === "" ? references : `${text}\n\n${references}`;
-      this.resetComposer();
-      await this.onSend?.(body, behavior);
-    } catch (error) {
-      this.attachmentError = error instanceof Error ? error.message : String(error);
-    } finally {
-      this.isSavingAttachments = false;
-    }
+    // Sending is owned by the controller (it drives the chat activity dock and,
+    // for folder mode, orchestrates the upload + reference rewrite), so this is
+    // fire-and-forget here.
+    void this.onSend?.(text, behavior, attachments, attachments === undefined ? undefined : delivery);
   }
 
   private resetComposer() {
diff --git a/src/client/src/components/shared.ts b/src/client/src/components/shared.ts
index 035ca7a..aa7f8ba 100644
--- a/src/client/src/components/shared.ts
+++ b/src/client/src/components/shared.ts
@@ -459,7 +459,6 @@ export const promptEditorStyles = css`
   .markdown-editor .cm-focused { outline: none; }
   .shell-mode textarea, .shell-mode .markdown-editor .cm-editor { border-color: var(--pi-success); box-shadow: 0 0 0 1px var(--pi-success-ring); }
   .mode-hint { position: absolute; right: 8px; bottom: 8px; max-width: calc(100% - 16px); border: 1px solid var(--pi-success-border); border-radius: 999px; background: var(--pi-success-surface); color: var(--pi-success); padding: 2px 8px; font-size: 12px; pointer-events: none; }
-  .sending-hint { border-color: var(--pi-accent-border); background: var(--pi-selection-bg); color: var(--pi-accent); }
   .attachments { display: flex; flex-wrap: wrap; align-items: center; gap: 8px; margin-top: 8px; }
   .attachment-chip { position: relative; width: 56px; height: 56px; border: 1px solid var(--pi-border); border-radius: 8px; overflow: hidden; background: var(--pi-bg); }
   .attachment-chip img { width: 100%; height: 100%; object-fit: cover; display: block; }
diff --git a/src/client/src/controllers/sessionController.test.ts b/src/client/src/controllers/sessionController.test.ts
index 820d9a7..245654f 100644
--- a/src/client/src/controllers/sessionController.test.ts
+++ b/src/client/src/controllers/sessionController.test.ts
@@ -1,5 +1,5 @@
 import { afterEach, describe, expect, it } from "vitest";
-import { api as defaultApi, type MessagePage, type SessionActivity, type SessionInfo, type SessionRef, type SessionStatus, type Workspace } from "../api";
+import { api as defaultApi, type MessagePage, type PromptAttachment, type SessionActivity, type SessionInfo, type SessionRef, type SessionStatus, type Workspace } from "../api";
 import { isCachedNewSessionInfo, loadCachedNewSessions, markCachedNewSessionInfo, rememberCachedNewSession } from "../cachedNewSessions";
 import { initialAppState, type AppState } from "../appState";
 import { machineSessionKey } from "../machineKeys";
@@ -142,6 +142,84 @@ describe("SessionController", () => {
     expect(state.selectedSession?.messageCount).toBe(3);
   });
 
+  it("toggles the sending state around an inline attachment send and forwards attachments", async () => {
+    let resolvePrompt: (() => void) | undefined;
+    const sendingDuringPrompt: boolean[] = [];
+    let promptArgs: { attachments?: PromptAttachment[] } | undefined;
+    let state: AppState = { ...initialAppState(), selectedWorkspace: workspace, selectedSession: oldSession, sessions: [oldSession] };
+    const attachments: PromptAttachment[] = [{ kind: "image", mimeType: "image/png", data: "QUJD", name: "shot.png" }];
+    const api: typeof defaultApi = {
+      ...defaultApi,
+      prompt: (_session, _text, _behavior, _machineId, sentAttachments) => new Promise<{ accepted: true }>((resolve) => {
+        promptArgs = { ...(sentAttachments === undefined ? {} : { attachments: sentAttachments }) };
+        resolvePrompt = () => { resolve({ accepted: true }); };
+      }),
+    };
+    const controller = new SessionController(
+      () => state,
+      (patch) => { state = { ...state, ...patch }; },
+      () => undefined,
+      undefined,
+      { api, socket: new FakeSocket() },
+    );
+
+    const send = controller.send("look", undefined, attachments, "inline");
+    sendingDuringPrompt.push(state.isSendingPrompt);
+    resolvePrompt?.();
+    await send;
+
+    expect(sendingDuringPrompt).toEqual([true]);
+    expect(state.isSendingPrompt).toBe(false);
+    expect(promptArgs).toEqual({ attachments });
+  });
+
+  it("uploads to the workspace folder and rewrites the prompt for folder delivery", async () => {
+    let savedCalledWith: PromptAttachment[] | undefined;
+    let promptText: string | undefined;
+    let promptAttachments: PromptAttachment[] | undefined;
+    let state: AppState = { ...initialAppState(), selectedWorkspace: workspace, selectedSession: oldSession, sessions: [oldSession] };
+    const attachments: PromptAttachment[] = [{ kind: "image", mimeType: "image/png", data: "QUJD", name: "shot.png" }];
+    const api: typeof defaultApi = {
+      ...defaultApi,
+      saveAttachments: (_session, sent) => { savedCalledWith = sent; return Promise.resolve([{ path: ".pi-web/paste/shot.png", mimeType: "image/png", size: 3 }]); },
+      prompt: (_session, text, _behavior, _machineId, sentAttachments) => { promptText = text; promptAttachments = sentAttachments; return Promise.resolve({ accepted: true }); },
+    };
+    const controller = new SessionController(
+      () => state,
+      (patch) => { state = { ...state, ...patch }; },
+      () => undefined,
+      undefined,
+      { api, socket: new FakeSocket() },
+    );
+
+    await controller.send("check this", undefined, attachments, "folder");
+
+    expect(savedCalledWith).toEqual(attachments);
+    expect(promptText).toBe("check this\n\n@.pi-web/paste/shot.png");
+    expect(promptAttachments).toBeUndefined();
+    expect(state.isSendingPrompt).toBe(false);
+  });
+
+  it("does not set the sending state for plain text messages", async () => {
+    let state: AppState = { ...initialAppState(), selectedWorkspace: workspace, selectedSession: oldSession, sessions: [oldSession] };
+    const seen: boolean[] = [];
+    const api: typeof defaultApi = {
+      ...defaultApi,
+      prompt: () => { seen.push(state.isSendingPrompt); return Promise.resolve({ accepted: true }); },
+    };
+    const controller = new SessionController(
+      () => state,
+      (patch) => { state = { ...state, ...patch }; },
+      () => undefined,
+      undefined,
+      { api, socket: new FakeSocket() },
+    );
+
+    await controller.send("hello");
+    expect(seen).toEqual([false]);
+    expect(state.isSendingPrompt).toBe(false);
+  });
+
   it("keeps live message count updates when a cached new session becomes persisted", async () => {
     const cachedSession = markCachedNewSessionInfo(oldSession);
     let resolvePrompt: (() => void) | undefined;
diff --git a/src/client/src/controllers/sessionController.ts b/src/client/src/controllers/sessionController.ts
index 96d8b00..554488b 100644
--- a/src/client/src/controllers/sessionController.ts
+++ b/src/client/src/controllers/sessionController.ts
@@ -6,6 +6,7 @@ import { machineSessionKey } from "../machineKeys";
 import { clearDraft, moveDraft, saveDraft } from "../promptDraftStorage";
 import { ChatTranscriptStore } from "../chatTranscriptStore";
 import { isShellInput } from "../inputModes";
+import { fileCompletionInsertText } from "../promptCompletions";
 import { SessionSocket, type GlobalSessionEvent, type SessionUiEvent } from "../sessionSocket";
 import { isSessionActive } from "../../../shared/activity";
 import { PI_WEB_CAPABILITIES, supportsPiWebCapability } from "../../../shared/capabilities";
@@ -63,7 +64,7 @@ export class SessionController {
     this.socket.close();
     this.catchupStreamSessionId = undefined;
     this.clearPendingTranscriptEvents();
-    this.setState({ selectedSession: undefined, messages: [], messagePageStart: 0, messagePageEnd: 0, messagePageTotal: 0, isLoadingEarlierMessages: false, isReceivingPartialStream: false, status: undefined, activity: undefined });
+    this.setState({ selectedSession: undefined, messages: [], messagePageStart: 0, messagePageEnd: 0, messagePageTotal: 0, isLoadingEarlierMessages: false, isReceivingPartialStream: false, isSendingPrompt: false, status: undefined, activity: undefined });
   }
 
   deselectSession(options?: { forgetRememberedSelection?: boolean | undefined; updateUrl?: boolean | undefined }) {
@@ -168,18 +169,32 @@ export class SessionController {
     }
   }
 
-  async send(text: string, streamingBehavior?: "steer" | "followUp", attachments?: PromptAttachment[]) {
+  async send(text: string, streamingBehavior?: "steer" | "followUp", attachments?: PromptAttachment[], delivery: "inline" | "folder" = "inline") {
     const trimmed = text.trim();
     const hasAttachments = attachments !== undefined && attachments.length > 0;
     if (!hasAttachments && trimmed.startsWith("/")) return this.runCommand(text);
     if (!hasAttachments && isShellInput(text)) return this.runShell(text);
     const session = this.getState().selectedSession;
     if (!session || session.archived === true) return;
+    // Surface a single optimistic sending state in the chat activity dock. It
+    // covers the pre-receipt window (upload, server-side image resizing,
+    // first-session open) and is superseded by real server activity/messages
+    // once api.prompt resolves.
+    if (hasAttachments) this.setState({ isSendingPrompt: true });
     try {
-      await this.api.prompt(session, text, streamingBehavior, selectedMachineId(this.getState()), attachments);
+      if (hasAttachments && delivery === "folder") {
+        const saved = await this.api.saveAttachments(session, attachments, selectedMachineId(this.getState()));
+        const references = saved.map((file) => fileCompletionInsertText(file.path, false)).join(" ");
+        const body = text === "" ? references : `${text}\n\n${references}`;
+        await this.api.prompt(session, body, streamingBehavior, selectedMachineId(this.getState()));
+      } else {
+        await this.api.prompt(session, text, streamingBehavior, selectedMachineId(this.getState()), attachments);
+      }
       this.markCachedNewSessionPersisted(session);
     } catch (error) {
       this.setState({ error: String(error) });
+    } finally {
+      if (hasAttachments) this.setState({ isSendingPrompt: false });
     }
   }
 
@@ -195,12 +210,6 @@ export class SessionController {
     }
   }
 
-  async saveAttachments(attachments: PromptAttachment[], folder?: string) {
-    const session = this.getState().selectedSession;
-    if (!session || session.archived === true || attachments.length === 0) return [];
-    return this.api.saveAttachments(session, attachments, selectedMachineId(this.getState()), folder);
-  }
-
   async runCommand(text: string) {
     const session = this.getState().selectedSession;
     if (!session || session.archived === true) return;