diff --git a/CHANGELOG.md b/CHANGELOG.md
index 2808121ec94..3ae028f7773 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -140,6 +140,7 @@ Docs: https://docs.openclaw.ai
 - Telegram/exec approvals: fall back to the origin session key for async approval followups and keep resume-failure status delivery sanitized so Telegram followups still land without leaking raw exec metadata. (#59351) Thanks @seonang.
 - Node-host/exec approvals: bind `pnpm dlx` invocations through the approval planner's mutable-script path so the effective runtime command is resolved for approval instead of being left unbound. (#58374)
 - Exec/node hosts: stop forwarding the gateway workspace cwd to remote node exec when no workdir was explicitly requested, so cross-platform node approvals fall back to the node default cwd instead of failing with `SYSTEM_RUN_DENIED`. (#58977) Thanks @Starhappysh.
+- TUI/chat: keep pending local sends visible and reconciled across history reloads, make busy/error recovery clearer through fallback and terminal-error paths, and reclaim transcript width for long links and paths. (#59800) Thanks @vincentkoc.
 - Exec approvals/channels: decouple initiating-surface approval availability from native delivery enablement so Telegram, Slack, and Discord still expose approvals when approvers exist and native target routing is configured separately. (#59776) Thanks @joelnishanth.
 - Plugins/runtime: reuse compatible active registries for `web_search` and `web_fetch` provider snapshot resolution so repeated runtime reads do not re-import the same bundled plugin set on each agent message. Related #48380.
 - Plugins/OpenAI: enable reference-image edits for `gpt-image-1` by routing edit calls to `/images/edits` with multipart image uploads, and update image-generation capability/docs metadata accordingly.
diff --git a/src/tui/components/assistant-message.ts b/src/tui/components/assistant-message.ts
index 89b97fc3396..99e1e928043 100644
--- a/src/tui/components/assistant-message.ts
+++ b/src/tui/components/assistant-message.ts
@@ -7,7 +7,7 @@ export class AssistantMessageComponent extends Container {
 
   constructor(text: string) {
     super();
-    this.body = new HyperlinkMarkdown(text, 1, 0, markdownTheme, {
+    this.body = new HyperlinkMarkdown(text, 0, 0, markdownTheme, {
       // Keep assistant body text in terminal default foreground so contrast
       // follows the user's terminal theme (dark or light).
       color: (line) => theme.assistantText(line),
diff --git a/src/tui/components/chat-log.test.ts b/src/tui/components/chat-log.test.ts
index a57de225f52..c5a1ce9a497 100644
--- a/src/tui/components/chat-log.test.ts
+++ b/src/tui/components/chat-log.test.ts
@@ -89,4 +89,61 @@ describe("ChatLog", () => {
     expect(rendered).not.toContain("BTW: what is 17 * 19?");
     expect(chatLog.hasVisibleBtw()).toBe(false);
   });
+
+  it("preserves pending user messages across history rebuilds", () => {
+    const chatLog = new ChatLog(40);
+
+    chatLog.addPendingUser("run-1", "queued hello");
+    chatLog.clearAll({ preservePendingUsers: true });
+    chatLog.addSystem("session agent:main:main");
+    chatLog.restorePendingUsers();
+
+    const rendered = chatLog.render(120).join("\n");
+    expect(rendered).toContain("queued hello");
+    expect(chatLog.countPendingUsers()).toBe(1);
+  });
+
+  it("does not append the same pending component twice when it is already mounted", () => {
+    const chatLog = new ChatLog(40);
+
+    chatLog.addPendingUser("run-1", "queued hello");
+    chatLog.restorePendingUsers();
+
+    expect(chatLog.children.length).toBe(1);
+    expect(chatLog.render(120).join("\n")).toContain("queued hello");
+  });
+
+  it("stops counting a pending user message once the run is committed", () => {
+    const chatLog = new ChatLog(40);
+
+    chatLog.addPendingUser("run-1", "hello");
+    expect(chatLog.countPendingUsers()).toBe(1);
+
+    expect(chatLog.commitPendingUser("run-1")).toBe(true);
+    expect(chatLog.countPendingUsers()).toBe(0);
+    expect(chatLog.render(120).join("\n")).toContain("hello");
+  });
+
+  it("reconciles pending users against rebuilt history using timestamps", () => {
+    const chatLog = new ChatLog(40);
+
+    chatLog.addPendingUser("run-1", "queued hello", 2_000);
+
+    expect(
+      chatLog.reconcilePendingUsers([
+        { text: "queued hello", timestamp: 2_100 },
+        { text: "older", timestamp: 1_000 },
+      ]),
+    ).toEqual(["run-1"]);
+    expect(chatLog.countPendingUsers()).toBe(0);
+  });
+
+  it("does not hide a new repeated prompt when only older history matches", () => {
+    const chatLog = new ChatLog(40);
+
+    chatLog.addPendingUser("run-1", "continue", 5_000);
+
+    expect(chatLog.reconcilePendingUsers([{ text: "continue", timestamp: 4_000 }])).toEqual([]);
+    expect(chatLog.countPendingUsers()).toBe(1);
+  });
 });
diff --git a/src/tui/components/chat-log.ts b/src/tui/components/chat-log.ts
index 07dd91d21c0..b1b789df3c7 100644
--- a/src/tui/components/chat-log.ts
+++ b/src/tui/components/chat-log.ts
@@ -10,6 +10,14 @@ export class ChatLog extends Container {
   private readonly maxComponents: number;
   private toolById = new Map<string, ToolExecutionComponent>();
   private streamingRuns = new Map<string, AssistantMessageComponent>();
+  private pendingUsers = new Map<
+    string,
+    {
+      component: UserMessageComponent;
+      text: string;
+      createdAt: number;
+    }
+  >();
   private btwMessage: BtwInlineMessage | null = null;
   private toolsExpanded = false;
 
@@ -29,6 +37,11 @@ export class ChatLog extends Container {
         this.streamingRuns.delete(runId);
       }
     }
+    for (const [runId, entry] of this.pendingUsers.entries()) {
+      if (entry.component === component) {
+        this.pendingUsers.delete(runId);
+      }
+    }
     if (this.btwMessage === component) {
       this.btwMessage = null;
     }
@@ -50,11 +63,30 @@ export class ChatLog extends Container {
     this.pruneOverflow();
   }
 
-  clearAll() {
+  clearAll(opts?: { preservePendingUsers?: boolean }) {
     this.clear();
     this.toolById.clear();
     this.streamingRuns.clear();
     this.btwMessage = null;
+    if (!opts?.preservePendingUsers) {
+      this.pendingUsers.clear();
+    }
+  }
+
+  restorePendingUsers() {
+    for (const entry of this.pendingUsers.values()) {
+      if (this.children.includes(entry.component)) {
+        continue;
+      }
+      this.append(entry.component);
+    }
+  }
+
+  clearPendingUsers() {
+    for (const entry of this.pendingUsers.values()) {
+      this.removeChild(entry.component);
+    }
+    this.pendingUsers.clear();
   }
 
   private createSystemMessage(text: string): Container {
@@ -72,6 +104,77 @@ export class ChatLog extends Container {
     this.append(new UserMessageComponent(text));
   }
 
+  addPendingUser(runId: string, text: string, createdAt = Date.now()) {
+    const existing = this.pendingUsers.get(runId);
+    if (existing) {
+      existing.text = text;
+      existing.createdAt = createdAt;
+      existing.component.setText(text);
+      return existing.component;
+    }
+    const component = new UserMessageComponent(text);
+    this.pendingUsers.set(runId, { component, text, createdAt });
+    this.append(component);
+    return component;
+  }
+
+  commitPendingUser(runId: string) {
+    return this.pendingUsers.delete(runId);
+  }
+
+  dropPendingUser(runId: string) {
+    const existing = this.pendingUsers.get(runId);
+    if (!existing) {
+      return false;
+    }
+    this.removeChild(existing.component);
+    this.pendingUsers.delete(runId);
+    return true;
+  }
+
+  hasPendingUser(runId: string) {
+    return this.pendingUsers.has(runId);
+  }
+
+  reconcilePendingUsers(
+    historyUsers: Array<{
+      text: string;
+      timestamp?: number | null;
+    }>,
+  ) {
+    const normalizedHistory = historyUsers
+      .map((entry) => ({
+        text: entry.text.trim(),
+        timestamp: typeof entry.timestamp === "number" ? entry.timestamp : null,
+      }))
+      .filter((entry) => entry.text.length > 0 && entry.timestamp !== null);
+    const clearedRunIds: string[] = [];
+    for (const [runId, entry] of this.pendingUsers.entries()) {
+      const pendingText = entry.text.trim();
+      if (!pendingText) {
+        continue;
+      }
+      const matchIndex = normalizedHistory.findIndex(
+        (historyEntry) =>
+          historyEntry.text === pendingText && (historyEntry.timestamp ?? 0) >= entry.createdAt,
+      );
+      if (matchIndex === -1) {
+        continue;
+      }
+      if (this.children.includes(entry.component)) {
+        this.removeChild(entry.component);
+      }
+      this.pendingUsers.delete(runId);
+      clearedRunIds.push(runId);
+      normalizedHistory.splice(matchIndex, 1);
+    }
+    return clearedRunIds;
+  }
+
+  countPendingUsers() {
+    return this.pendingUsers.size;
+  }
+
   private resolveRunId(runId?: string) {
     return runId ?? "default";
   }
diff --git a/src/tui/components/custom-editor.test.ts b/src/tui/components/custom-editor.test.ts
new file mode 100644
index 00000000000..31728eb8279
--- /dev/null
+++ b/src/tui/components/custom-editor.test.ts
@@ -0,0 +1,32 @@
+import { TUI } from "@mariozechner/pi-tui";
+import { afterEach, describe, expect, it, vi } from "vitest";
+import { editorTheme } from "../theme/theme.js";
+import { CustomEditor } from "./custom-editor.js";
+
+describe("CustomEditor", () => {
+  afterEach(() => {
+    vi.restoreAllMocks();
+  });
+
+  it("routes alt+enter to the follow-up handler", () => {
+    const tui = { requestRender: vi.fn() } as unknown as TUI;
+    const editor = new CustomEditor(tui, editorTheme);
+    const onAltEnter = vi.fn();
+    editor.onAltEnter = onAltEnter;
+
+    editor.handleInput("\u001b\r");
+
+    expect(onAltEnter).toHaveBeenCalledTimes(1);
+  });
+
+  it("routes alt+up to the dequeue handler", () => {
+    const tui = { requestRender: vi.fn() } as unknown as TUI;
+    const editor = new CustomEditor(tui, editorTheme);
+    const onAltUp = vi.fn();
+    editor.onAltUp = onAltUp;
+
+    editor.handleInput("\u001bp");
+
+    expect(onAltUp).toHaveBeenCalledTimes(1);
+  });
+});
diff --git a/src/tui/components/custom-editor.ts b/src/tui/components/custom-editor.ts
index 4dc42391f2e..4efc8acb18a 100644
--- a/src/tui/components/custom-editor.ts
+++ b/src/tui/components/custom-editor.ts
@@ -11,12 +11,17 @@ export class CustomEditor extends Editor {
   onCtrlT?: () => void;
   onShiftTab?: () => void;
   onAltEnter?: () => void;
+  onAltUp?: () => void;
 
   handleInput(data: string): void {
     if (matchesKey(data, Key.alt("enter")) && this.onAltEnter) {
       this.onAltEnter();
       return;
     }
+    if (matchesKey(data, Key.alt("up")) && this.onAltUp) {
+      this.onAltUp();
+      return;
+    }
     if (matchesKey(data, Key.ctrl("l")) && this.onCtrlL) {
       this.onCtrlL();
       return;
diff --git a/src/tui/components/markdown-message.ts b/src/tui/components/markdown-message.ts
index fca84d0d524..12dc935a6ad 100644
--- a/src/tui/components/markdown-message.ts
+++ b/src/tui/components/markdown-message.ts
@@ -1,14 +1,15 @@
-import { Container, Markdown, Spacer } from "@mariozechner/pi-tui";
+import { Container, Spacer } from "@mariozechner/pi-tui";
 import { markdownTheme } from "../theme/theme.js";
+import { HyperlinkMarkdown } from "./hyperlink-markdown.js";
 
-type MarkdownOptions = ConstructorParameters<typeof Markdown>[4];
+type MarkdownOptions = ConstructorParameters<typeof HyperlinkMarkdown>[4];
 
 export class MarkdownMessageComponent extends Container {
-  private body: Markdown;
+  private body: HyperlinkMarkdown;
 
   constructor(text: string, y: number, options?: MarkdownOptions) {
     super();
-    this.body = new Markdown(text, 1, y, markdownTheme, options);
+    this.body = new HyperlinkMarkdown(text, 0, y, markdownTheme, options);
     this.addChild(new Spacer(1));
     this.addChild(this.body);
   }
diff --git a/src/tui/components/pending-messages.test.ts b/src/tui/components/pending-messages.test.ts
new file mode 100644
index 00000000000..9a7fae3dcc6
--- /dev/null
+++ b/src/tui/components/pending-messages.test.ts
@@ -0,0 +1,25 @@
+import { describe, expect, it } from "vitest";
+import { PendingMessagesComponent } from "./pending-messages.js";
+
+describe("PendingMessagesComponent", () => {
+  it("renders queued steering and follow-up messages", () => {
+    const component = new PendingMessagesComponent();
+    component.setMessages([
+      { runId: "run-1", text: "continue", mode: "steer" },
+      { runId: "run-2", text: "after that, write tests", mode: "followUp" },
+    ]);
+
+    const rendered = component.render(120).join("\n");
+    expect(rendered).toContain("Steer: continue");
+    expect(rendered).toContain("Follow-up: after that, write tests");
+    expect(rendered).toContain("alt+up");
+  });
+
+  it("clears its output when no queued messages remain", () => {
+    const component = new PendingMessagesComponent();
+    component.setMessages([{ runId: "run-1", text: "continue", mode: "steer" }]);
+    component.clearMessages();
+
+    expect(component.render(120).join("\n")).toBe("");
+  });
+});
diff --git a/src/tui/components/pending-messages.ts b/src/tui/components/pending-messages.ts
new file mode 100644
index 00000000000..ba899d76a7c
--- /dev/null
+++ b/src/tui/components/pending-messages.ts
@@ -0,0 +1,35 @@
+import { Container, Spacer, Text } from "@mariozechner/pi-tui";
+import { theme } from "../theme/theme.js";
+import type { QueuedMessage } from "../tui-types.js";
+
+function formatLabel(mode: QueuedMessage["mode"]) {
+  return mode === "followUp" ? "Follow-up" : "Steer";
+}
+
+export class PendingMessagesComponent extends Container {
+  private messages: QueuedMessage[] = [];
+
+  setMessages(messages: QueuedMessage[]) {
+    this.messages = [...messages];
+    this.renderMessages();
+  }
+
+  clearMessages() {
+    this.messages = [];
+    this.renderMessages();
+  }
+
+  private renderMessages() {
+    this.clear();
+    if (this.messages.length === 0) {
+      return;
+    }
+
+    this.addChild(new Spacer(1));
+    for (const message of this.messages) {
+      const label = formatLabel(message.mode);
+      this.addChild(new Text(theme.dim(`${label}: ${message.text}`), 1, 0));
+    }
+    this.addChild(new Text(theme.dim("↳ alt+up to restore queued messages"), 1, 0));
+  }
+}
diff --git a/src/tui/tui-types.ts b/src/tui/tui-types.ts
index 03d0cacbc5a..5523d8b1ec8 100644
--- a/src/tui/tui-types.ts
+++ b/src/tui/tui-types.ts
@@ -60,6 +60,14 @@ export type AgentSummary = {
   name?: string;
 };
 
+export type QueuedMessageMode = "steer" | "followUp";
+
+export type QueuedMessage = {
+  runId: string;
+  text: string;
+  mode: QueuedMessageMode;
+};
+
 export type GatewayStatusSummary = {
   runtimeVersion?: string | null;
   linkChannel?: {
@@ -109,6 +117,7 @@ export type TuiStateAccess = {
   currentSessionId: string | null;
   activeChatRunId: string | null;
   pendingOptimisticUserMessage?: boolean;
+  queuedMessages?: QueuedMessage[];
   historyLoaded: boolean;
   sessionInfo: SessionInfo;
   initialSessionApplied: boolean;