diff --git a/prompts/whatsapp.md b/prompts/whatsapp.md
index ffd921e36..0560187ea 100644
--- a/prompts/whatsapp.md
+++ b/prompts/whatsapp.md
@@ -46,6 +46,25 @@ the file path is in the message, so you can read it immediately.
 - No forum topics, no custom admin titles, no stopping a poll.
 - Pins expire (24h, 7d, or 30d) and only pins Talon placed are listable.
 
+### Continuity — your context is not the chat
+
+Your working context can start fresh at any time (a `/reset`, a daemon
+restart, an overflowed session) while the WhatsApp conversation continues
+uninterrupted. The chat's real record lives in persistent history, both
+sides of it, and you can always get it back:
+
+- `read_chat_history` — the recent messages; pass `offset_id` (a msg_id)
+  or `before` (an ISO date) to page further back.
+- `search_chat_history` — keyword search over everything said in this
+  chat, including your own earlier messages.
+- `get_message_by_id` — one specific message when you hold its id.
+
+If the sender references something you don't recognize — "the flights",
+"what you said yesterday", "that plan" — search the history before
+saying you don't know or asking them to repeat themselves. A fresh
+session is your situation, not theirs; to the person on the phone this
+is one long conversation, and it should read like you remember it.
+
 ### Staying silent
 
 Reactions work here, so a react is the light acknowledgement when a
diff --git a/src/__tests__/whatsapp-continuity.test.ts b/src/__tests__/whatsapp-continuity.test.ts
new file mode 100644
index 000000000..49c3f47cf
--- /dev/null
+++ b/src/__tests__/whatsapp-continuity.test.ts
@@ -0,0 +1,345 @@
+/**
+ * WhatsApp session continuity — the pieces that make a fresh session able
+ * to reconstruct the conversation, and a broken turn visible in the chat.
+ *
+ * 1. Outbound recording: the bot's own replies must land in persistent
+ *    history, or read/search_chat_history shows a one-sided chat.
+ * 2. Id seeding: the in-memory msg-id counter restarts at its base every
+ *    boot while history persists; unseeded, post-restart messages re-issue
+ *    ids INSERT OR IGNORE silently drops.
+ * 3. Paging: the read_history fallback must honor offset_id/before — the
+ *    tool schema advertises them, and WhatsApp has no platform override.
+ * 4. Turn recovery: a failed turn must surface a friendly error in the
+ *    chat (with one retry for brief transients), not just a log line.
+ */
+
+import { beforeEach, describe, expect, it, vi } from "vitest";
+
+vi.mock("../util/log.js", () => ({
+  log: vi.fn(),
+  logError: vi.fn(),
+  logWarn: vi.fn(),
+  logDebug: vi.fn(),
+}));
+
+import {
+  rememberMessage,
+  resetMessageStore,
+  seedMessageStore,
+  lookupMessage,
+} from "../frontend/whatsapp/message-store.js";
+import {
+  sendContent,
+  setWhatsAppBotName,
+} from "../frontend/whatsapp/actions/shared.js";
+import {
+  runTurnWithRecovery,
+  shouldReplyToCatchUp,
+  CATCH_UP_REPLY_WINDOW_MS,
+} from "../frontend/whatsapp/turn-recovery.js";
+import { historyHandlers } from "../core/engine/gateway-actions/history.js";
+import {
+  pushMessage,
+  getRecentHistory,
+  maxMsgIdForChatPrefix,
+} from "../storage/history.js";
+import { deleteChat } from "../storage/repositories/history-repo.js";
+import { TalonError } from "../core/errors.js";
+
+const CHAT = "wa_dm_5550001";
+
+const fakeChat = {
+  chatId: CHAT,
+  numericChatId: 900001,
+  jid: "5550001@s.whatsapp.net",
+  isGroup: false,
+} as never;
+
+function fakeCtx(sendResult: unknown = undefined) {
+  const sock = {
+    sendMessage: vi.fn(async () => sendResult),
+  };
+  const gateway = { incrementMessages: vi.fn() };
+  return { sock: sock as never, gateway, mocks: { sock } };
+}
+
+beforeEach(() => {
+  resetMessageStore();
+  deleteChat(CHAT);
+  deleteChat("wa_dm_other");
+});
+
+describe("outbound history recording", () => {
+  it("persists the bot's reply alongside inbound messages", async () => {
+    setWhatsAppBotName("Talon");
+    pushMessage(CHAT, {
+      msgId: 1_000_000,
+      senderId: 42,
+      senderName: "Dylan",
+      text: "what time is the flight?",
+      timestamp: Date.now() - 1000,
+    });
+
+    const ctx = fakeCtx({ key: { id: "WA1", remoteJid: "x", fromMe: true } });
+    seedMessageStore(1_000_001);
+    await sendContent(ctx, fakeChat, { text: "Departure is 07:35 from DUB." });
+
+    const rows = getRecentHistory(CHAT, 10);
+    expect(rows.map((r) => [r.senderName, r.text])).toEqual([
+      ["Dylan", "what time is the flight?"],
+      ["Talon", "Departure is 07:35 from DUB."],
+    ]);
+    // The bot row uses the cross-frontend assistant sender id.
+    expect(rows[1].senderId).toBe(0);
+  });
+
+  it("records media sends with their caption and type", async () => {
+    const ctx = fakeCtx({ key: { id: "WA2", remoteJid: "x", fromMe: true } });
+    await sendContent(ctx, fakeChat, {
+      image: { url: "/tmp/x.jpg" },
+      caption: "the boarding pass",
+    } as never);
+
+    const [row] = getRecentHistory(CHAT, 1);
+    expect(row.text).toBe("the boarding pass");
+    expect(row.mediaType).toBe("photo");
+  });
+
+  it("does not write empty rows for reaction-like payloads", async () => {
+    const ctx = fakeCtx({ key: { id: "WA3", remoteJid: "x", fromMe: true } });
+    // Location has no text/caption and no history media type → marker text.
+    await sendContent(ctx, fakeChat, {
+      location: { degreesLatitude: 1, degreesLongitude: 2 },
+    } as never);
+    const rows = getRecentHistory(CHAT, 5);
+    expect(rows).toHaveLength(1);
+    expect(rows[0].text).toBe("[location]");
+  });
+});
+
+describe("message-id seeding across restarts", () => {
+  it("continues past what history already holds", () => {
+    // Simulate the previous run: history rows up to 1_000_012.
+    pushMessage(CHAT, {
+      msgId: 1_000_012,
+      senderId: 42,
+      senderName: "Dylan",
+      text: "old",
+      timestamp: Date.now(),
+    });
+
+    // Simulate the restart: fresh counter, then the boot-time seed.
+    resetMessageStore();
+    seedMessageStore((maxMsgIdForChatPrefix("wa_") ?? 0) + 1);
+
+    const id = rememberMessage({
+      key: { id: "WAX", remoteJid: "x" },
+      chatId: CHAT,
+    });
+    expect(id).toBeGreaterThan(1_000_012);
+
+    // And the history insert is not silently IGNOREd.
+    pushMessage(CHAT, {
+      msgId: id,
+      senderId: 42,
+      senderName: "Dylan",
+      text: "new after restart",
+      timestamp: Date.now(),
+    });
+    const rows = getRecentHistory(CHAT, 10);
+    expect(rows.map((r) => r.text)).toContain("new after restart");
+  });
+
+  it("matches the wa_ prefix literally, not as a LIKE wildcard", () => {
+    // "waX..." must not satisfy the "wa_" prefix — _ is a LIKE wildcard
+    // unless escaped, and an unescaped match would seed from foreign chats.
+    pushMessage("waXfoo", {
+      msgId: 9_999_999,
+      senderId: 1,
+      senderName: "x",
+      text: "not a whatsapp chat",
+      timestamp: Date.now(),
+    });
+    try {
+      expect(maxMsgIdForChatPrefix("wa_") ?? 0).toBeLessThan(9_999_999);
+    } finally {
+      deleteChat("waXfoo");
+    }
+  });
+
+  it("never lowers the counter", () => {
+    seedMessageStore(2_000_000);
+    seedMessageStore(5); // a later, lower seed must not rewind
+    const id = rememberMessage({
+      key: { id: "WAY", remoteJid: "x" },
+      chatId: CHAT,
+    });
+    expect(id).toBeGreaterThanOrEqual(2_000_000);
+    expect(lookupMessage(id)?.chatId).toBe(CHAT);
+  });
+});
+
+describe("read_history fallback paging", () => {
+  beforeEach(() => {
+    const base = Date.parse("2026-08-01T00:00:00Z");
+    for (let i = 0; i < 10; i++) {
+      pushMessage(CHAT, {
+        msgId: 1_000_000 + i,
+        senderId: 42,
+        senderName: "Dylan",
+        text: `message ${i}`,
+        timestamp: base + i * 60_000,
+      });
+    }
+  });
+
+  it("pages back with offset_id", async () => {
+    const res = (await historyHandlers.read_history(
+      { offset_id: 1_000_005, limit: 3 },
+      CHAT as never,
+    )) as { ok: boolean; text: string };
+    expect(res.ok).toBe(true);
+    expect(res.text).toContain("message 2");
+    expect(res.text).toContain("message 4");
+    expect(res.text).not.toContain("message 5");
+    expect(res.text).not.toContain("message 9");
+  });
+
+  it("pages back with a before date", async () => {
+    const res = (await historyHandlers.read_history(
+      { before: "2026-08-01T00:03:00Z", limit: 10 },
+      CHAT as never,
+    )) as { ok: boolean; text: string };
+    expect(res.text).toContain("message 2");
+    expect(res.text).not.toContain("message 3");
+  });
+
+  it("still returns the newest window with no cursor", async () => {
+    const res = (await historyHandlers.read_history(
+      { limit: 2 },
+      CHAT as never,
+    )) as {
+      ok: boolean;
+      text: string;
+    };
+    expect(res.text).toContain("message 9");
+    expect(res.text).not.toContain("message 0");
+  });
+
+  it("ignores an unparseable before date rather than failing", async () => {
+    const res = (await historyHandlers.read_history(
+      { before: "not-a-date", limit: 2 },
+      CHAT as never,
+    )) as { ok: boolean; text: string };
+    expect(res.ok).toBe(true);
+    expect(res.text).toContain("message 9");
+  });
+});
+
+describe("turn recovery — errors reach the chat", () => {
+  const noWait = () => Promise.resolve();
+
+  it("sends a friendly error for a non-retryable failure", async () => {
+    const sent: string[] = [];
+    await runTurnWithRecovery({
+      chatId: CHAT,
+      senderName: "Dylan",
+      runTurn: async () => {
+        throw new TalonError("boom", { reason: "unknown" });
+      },
+      sendErrorText: async (t) => {
+        sent.push(t);
+      },
+      wait: noWait,
+    });
+    expect(sent).toHaveLength(1);
+    expect(sent[0].length).toBeGreaterThan(0);
+  });
+
+  it("retries a transient once and stays silent when the retry succeeds", async () => {
+    const sent: string[] = [];
+    let calls = 0;
+    await runTurnWithRecovery({
+      chatId: CHAT,
+      senderName: "Dylan",
+      runTurn: async () => {
+        calls++;
+        if (calls === 1)
+          throw new TalonError("overloaded", {
+            reason: "overloaded",
+            retryable: true,
+          });
+      },
+      sendErrorText: async (t) => {
+        sent.push(t);
+      },
+      wait: noWait,
+    });
+    expect(calls).toBe(2);
+    expect(sent).toHaveLength(0);
+  });
+
+  it("reports the failure when the retry also fails", async () => {
+    const sent: string[] = [];
+    await runTurnWithRecovery({
+      chatId: CHAT,
+      senderName: "Dylan",
+      runTurn: async () => {
+        throw new TalonError("overloaded", {
+          reason: "overloaded",
+          retryable: true,
+        });
+      },
+      sendErrorText: async (t) => {
+        sent.push(t);
+      },
+      wait: noWait,
+    });
+    expect(sent).toHaveLength(1);
+  });
+
+  it("stays silent for a user-initiated stop", async () => {
+    const sent: string[] = [];
+    await runTurnWithRecovery({
+      chatId: CHAT,
+      senderName: "Dylan",
+      runTurn: async () => {
+        throw new TalonError("Turn stopped by user", { reason: "stopped" });
+      },
+      sendErrorText: async (t) => {
+        sent.push(t);
+      },
+      wait: noWait,
+    });
+    expect(sent).toHaveLength(0);
+  });
+});
+
+describe("catch-up (offline-queued) reply policy", () => {
+  it("replies to a message queued during a short restart", () => {
+    const now = Date.parse("2026-08-23T12:00:00Z");
+    const fiveMinAgo = now - 5 * 60_000;
+    expect(shouldReplyToCatchUp(fiveMinAgo, now)).toBe(true);
+  });
+
+  it("records but does not reply past the window", () => {
+    const now = Date.parse("2026-08-23T12:00:00Z");
+    const hourAgo = now - 60 * 60_000;
+    expect(shouldReplyToCatchUp(hourAgo, now)).toBe(false);
+  });
+
+  it("is inclusive at the boundary", () => {
+    const now = Date.parse("2026-08-23T12:00:00Z");
+    expect(shouldReplyToCatchUp(now - CATCH_UP_REPLY_WINDOW_MS, now)).toBe(
+      true,
+    );
+    expect(shouldReplyToCatchUp(now - CATCH_UP_REPLY_WINDOW_MS - 1, now)).toBe(
+      false,
+    );
+  });
+
+  it("treats a missing timestamp as fresh — better one odd reply than a dropped question", () => {
+    expect(shouldReplyToCatchUp(0)).toBe(true);
+    expect(shouldReplyToCatchUp(Number.NaN)).toBe(true);
+  });
+});
diff --git a/src/core/engine/gateway-actions/history.ts b/src/core/engine/gateway-actions/history.ts
index cebaa2eba..61efcbd03 100644
--- a/src/core/engine/gateway-actions/history.ts
+++ b/src/core/engine/gateway-actions/history.ts
@@ -5,6 +5,8 @@
 
 import {
   getRecentFormatted,
+  getFormattedBefore,
+  getFormattedBeforeTime,
   searchHistory,
   getMessagesByUser,
   getKnownUsers,
@@ -15,7 +17,23 @@ import type { SharedActionHandlers } from "./types.js";
 export const historyHandlers: SharedActionHandlers = {
   read_history: (body, chatId) => {
     const limit = Math.min(100, Number(body.limit ?? 30));
-    return { ok: true, text: getRecentFormatted(String(chatId), limit) };
+    const cid = String(chatId);
+    // The tool schema advertises `offset_id` and `before` for paging back;
+    // this fallback used to ignore both and hand back the same newest
+    // window no matter what the model asked, so "go further back" was a
+    // silent no-op on frontends without a platform history API (WhatsApp,
+    // native).
+    const offsetId = Number(body.offset_id);
+    if (Number.isFinite(offsetId) && offsetId > 0) {
+      return { ok: true, text: getFormattedBefore(cid, offsetId, limit) };
+    }
+    if (body.before !== undefined) {
+      const ts = Date.parse(String(body.before));
+      if (Number.isFinite(ts)) {
+        return { ok: true, text: getFormattedBeforeTime(cid, ts, limit) };
+      }
+    }
+    return { ok: true, text: getRecentFormatted(cid, limit) };
   },
 
   search_history: (body, chatId) => {
diff --git a/src/frontend/shared/session-status.ts b/src/frontend/shared/session-status.ts
index ae6f8fb9f..cfd965153 100644
--- a/src/frontend/shared/session-status.ts
+++ b/src/frontend/shared/session-status.ts
@@ -44,6 +44,7 @@ import { formatDuration } from "./format.js";
 export async function performSessionReset(
   chatId: string,
   backend: Backend | null | undefined,
+  opts: { keepHistory?: boolean } = {},
 ): Promise<void> {
   const info = getSessionInfo(chatId);
   if (info.turns > 0) {
@@ -59,7 +60,12 @@ export async function performSessionReset(
     );
   }
   resetSession(chatId);
-  clearHistory(chatId);
+  // Frontends whose platform keeps the real chat record (Telegram,
+  // Discord) clear the local mirror too — the platform still has
+  // everything. WhatsApp passes keepHistory: the local store is the ONLY
+  // record there, and wiping it on /reset would destroy exactly what the
+  // continuity tools (read/search_chat_history) exist to recover.
+  if (!opts.keepHistory) clearHistory(chatId);
   resetPulseCheckpoint(chatId);
   backend?.sessions?.resetChat?.(chatId);
   await backend?.sessions?.warmSession?.(chatId);
diff --git a/src/frontend/whatsapp/actions/shared.ts b/src/frontend/whatsapp/actions/shared.ts
index dad0816d3..1c869bfd7 100644
--- a/src/frontend/whatsapp/actions/shared.ts
+++ b/src/frontend/whatsapp/actions/shared.ts
@@ -12,6 +12,7 @@ import { log, logError } from "../../../util/log.js";
 import type { ActionResult } from "../../../core/types.js";
 import { toWhatsAppChunks } from "../formatting.js";
 import { lookupMessage, rememberMessage } from "../message-store.js";
+import { pushMessage, type HistoryMessage } from "../../../storage/history.js";
 import type { WhatsAppChatInfo } from "../registry.js";
 
 /** WhatsApp's own ceiling for a media upload. */
@@ -128,6 +129,40 @@ export function resolveQuoted(
   );
 }
 
+/**
+ * How the bot signs its own rows in persistent history. Set once at
+ * frontend start from `config.botDisplayName`; the 0 sender id is the
+ * cross-frontend "this is the assistant" convention (native/protocol.ts).
+ */
+let botName = "Talon";
+export function setWhatsAppBotName(name: string): void {
+  if (name.trim()) botName = name.trim();
+}
+
+/**
+ * History labels for outbound media, in HistoryMessage's closed
+ * vocabulary. Payloads with no file analogue (polls, locations, contact
+ * cards) return a text marker instead via `outboundTextMarker`.
+ */
+function outboundMediaType(
+  content: AnyMessageContent,
+): NonNullable<HistoryMessage["mediaType"]> | undefined {
+  if ("image" in content) return "photo";
+  if ("video" in content) return content.gifPlayback ? "animation" : "video";
+  if ("audio" in content) return "voice";
+  if ("sticker" in content) return "sticker";
+  if ("document" in content) return "document";
+  return undefined;
+}
+
+/** A readable stand-in for captionless payloads history can't type. */
+function outboundTextMarker(content: AnyMessageContent): string {
+  if ("poll" in content) return `[poll: ${content.poll.name}]`;
+  if ("location" in content) return "[location]";
+  if ("contacts" in content) return "[contact card]";
+  return "";
+}
+
 /**
  * Send one content payload, remember the resulting message so later
  * tool calls can address it, and report its Talon numeric id.
@@ -141,13 +176,35 @@ export async function sendContent(
   const sent = await ctx.sock.sendMessage(chat.jid, content, options);
   ctx.gateway.incrementMessages(chat.numericChatId);
   if (!sent?.key) return { ok: true };
+  const text =
+    "text" in content
+      ? String(content.text ?? "")
+      : "caption" in content && content.caption
+        ? String(content.caption)
+        : outboundTextMarker(content);
   const msgId = rememberMessage({
     key: sent.key,
     chatId: chat.chatId,
     message: sent,
-    text: "text" in content ? String(content.text ?? "") : "",
+    text,
     senderName: "bot",
   });
+  // Persist the bot's side of the conversation. Without this the history
+  // store held only inbound messages, so read_chat_history showed a
+  // one-sided chat and search_chat_history could never find anything the
+  // bot itself had said — exactly the messages a fresh session needs when
+  // reconstructing context after a reset or restart.
+  const mediaType = outboundMediaType(content);
+  if (text || mediaType) {
+    pushMessage(chat.chatId, {
+      msgId,
+      senderId: 0,
+      senderName: botName,
+      text,
+      timestamp: Date.now(),
+      ...(mediaType ? { mediaType } : {}),
+    });
+  }
   return { ok: true, message_id: msgId };
 }
 
diff --git a/src/frontend/whatsapp/index.ts b/src/frontend/whatsapp/index.ts
index 2a9d18aea..26a6c7c0a 100644
--- a/src/frontend/whatsapp/index.ts
+++ b/src/frontend/whatsapp/index.ts
@@ -33,12 +33,10 @@ import { toolInputToRecord } from "../../core/agent-runtime/events.js";
 import { resolveChatBackend } from "../../core/engine/backend-controller/index.js";
 import { performSessionReset } from "../shared/session-status.js";
 import { appendDailyLog } from "../../storage/daily-log.js";
-import { pushMessage } from "../../storage/history.js";
+import { pushMessage, maxMsgIdForChatPrefix } from "../../storage/history.js";
 import {
-  recordError,
   recordMessageProcessed,
   recordMessageReceived,
-  recordMessageSettled,
 } from "../../util/watchdog.js";
 import { createWhatsAppActionHandler } from "./actions/index.js";
 import {
@@ -47,9 +45,14 @@ import {
   identityAllowed,
   resolveIdentity,
 } from "./identity.js";
-import { sendText } from "./actions/shared.js";
+import { sendText, setWhatsAppBotName } from "./actions/shared.js";
 import { saveInboundMedia } from "./media-store.js";
-import { lookupByWaId, rememberMessage } from "./message-store.js";
+import {
+  lookupByWaId,
+  rememberMessage,
+  seedMessageStore,
+} from "./message-store.js";
+import { runTurnWithRecovery, shouldReplyToCatchUp } from "./turn-recovery.js";
 import {
   lookupWhatsAppChat,
   registerWhatsAppChat,
@@ -217,7 +220,10 @@ export function createWhatsAppFrontend(
     return Boolean(ctx?.participant && isSelf(ctx.participant));
   }
 
-  async function handleInbound(msg: WAMessage): Promise<void> {
+  async function handleInbound(
+    msg: WAMessage,
+    opts: { catchUp?: boolean } = {},
+  ): Promise<void> {
     const jid = msg.key.remoteJid;
     // `fromMe` covers our own sends echoing back; status@broadcast is the
     // Stories feed, which is not a conversation.
@@ -278,13 +284,17 @@ export function createWhatsAppFrontend(
     const replyToWaId =
       msg.message?.extendedTextMessage?.contextInfo?.stanzaId ?? undefined;
     const replyTo = replyToWaId ? lookupByWaId(replyToWaId) : undefined;
+    const platformTs = Number(msg.messageTimestamp) * 1000;
     pushMessage(chat.chatId, {
       msgId,
       senderId: Number(BigInt(canonicalId(identity) ?? "0") % 2147483647n),
       senderName,
       senderHandle: canonicalId(identity),
       text,
-      timestamp: Date.now(),
+      // The platform timestamp, so a catch-up message recorded late still
+      // reads in true order; Date.now() only when Baileys omits it.
+      timestamp:
+        Number.isFinite(platformTs) && platformTs > 0 ? platformTs : Date.now(),
       ...(replyTo ? { replyToMsgId: replyTo.msgId } : {}),
       ...(media ? { mediaType: media.type, filePath: media.filePath } : {}),
     });
@@ -295,6 +305,9 @@ export function createWhatsAppFrontend(
       await performSessionReset(
         chat.chatId,
         resolveChatBackend(chat.chatId, gateway.backend),
+        // The local history store is WhatsApp's only chat record — a
+        // reset clears the model's session, not the conversation log.
+        { keepHistory: true },
       );
       log("whatsapp", `Session reset by ${senderName}`);
       if (sock) {
@@ -310,13 +323,31 @@ export function createWhatsAppFrontend(
         await sendText(
           { sock, gateway },
           chat,
-          "*Commands*\n/reset — clear session & history\n/help — this message",
+          "*Commands*\n/reset — start a fresh session (chat log kept)\n/help — this message",
         ).catch(() => {});
       }
       recordMessageProcessed();
       return;
     }
 
+    // Catch-up messages (queued while the daemon was down) get a reply
+    // turn only while fresh; stale ones are already recorded above and
+    // the next live turn reads them from history.
+    if (opts.catchUp) {
+      if (!shouldReplyToCatchUp(platformTs)) {
+        log(
+          "whatsapp",
+          `[${chat.chatId}] Recorded offline message from ${senderName} (history only — too old for a reply turn)`,
+        );
+        recordMessageProcessed();
+        return;
+      }
+      log(
+        "whatsapp",
+        `[${chat.chatId}] Catch-up: replying to offline message from ${senderName}`,
+      );
+    }
+
     const preview = text || `(${media?.type ?? "media"})`;
     log(
       "whatsapp",
@@ -334,8 +365,8 @@ export function createWhatsAppFrontend(
       : "";
     const prompt = `[${senderName}] msg_id:${msgId}: ${text}${mediaNote}`;
 
-    try {
-      await execute({
+    const runTurn = () =>
+      execute({
         chatId: chat.chatId,
         numericChatId: chat.numericChatId,
         prompt,
@@ -374,13 +405,23 @@ export function createWhatsAppFrontend(
           }
         },
       });
-      recordMessageProcessed();
-    } catch (err) {
-      const message = err instanceof Error ? err.message : String(err);
-      logError("whatsapp", `[${chat.chatId}] execute failed: ${message}`);
-      recordError(message);
-      recordMessageSettled();
-    }
+
+    await runTurnWithRecovery({
+      chatId: chat.chatId,
+      senderName,
+      runTurn,
+      sendErrorText: async (text) => {
+        if (!sock) return;
+        try {
+          await sendText({ sock, gateway }, chat, text);
+        } catch (sendErr) {
+          logError(
+            "whatsapp",
+            `error delivery failed: ${sendErr instanceof Error ? sendErr.message : sendErr}`,
+          );
+        }
+      },
+    });
   }
 
   /** One socket lifetime. Resolves with what the caller should do next. */
@@ -397,11 +438,18 @@ export function createWhatsAppFrontend(
     socket.ev.on("creds.update", saveCreds);
 
     socket.ev.on("messages.upsert", ({ messages, type }) => {
-      // "notify" is a live message; "append" is history sync, which must
-      // not trigger turns for conversations that already happened.
-      if (type !== "notify") return;
+      // "notify" is a live message. "append" is everything delivered out
+      // of band — chiefly messages QUEUED WHILE THE DAEMON WAS DOWN
+      // (Baileys marks offline-queued nodes as append), but also our own
+      // sends echoing back and newsletter posts, which handleInbound's
+      // fromMe/allowlist gates drop. Dropping append wholesale meant any
+      // message sent during a restart simply vanished: never recorded,
+      // never answered. Appends are processed as catch-up: always
+      // recorded, replied to only while fresh.
+      if (type !== "notify" && type !== "append") return;
+      const catchUp = type === "append";
       for (const msg of messages) {
-        void handleInbound(msg).catch((err) => {
+        void handleInbound(msg, { catchUp }).catch((err) => {
           logError(
             "whatsapp",
             `inbound handler failed: ${err instanceof Error ? err.message : err}`,
@@ -498,6 +546,12 @@ export function createWhatsAppFrontend(
     getBridgePort: () => gateway.getPort(),
 
     async init() {
+      setWhatsAppBotName(config.botDisplayName);
+      // The in-memory message-id counter restarts at its base every boot,
+      // but history persists — seed it past what the table already holds
+      // so post-restart messages don't re-issue ids INSERT OR IGNORE then
+      // silently drops (chat ids all start with "wa_").
+      seedMessageStore((maxMsgIdForChatPrefix("wa_") ?? 0) + 1);
       gateway.registerFrontendHandler(
         "whatsapp",
         createWhatsAppActionHandler(() => sock, gateway),
diff --git a/src/frontend/whatsapp/message-store.ts b/src/frontend/whatsapp/message-store.ts
index a63190c00..26a41e384 100644
--- a/src/frontend/whatsapp/message-store.ts
+++ b/src/frontend/whatsapp/message-store.ts
@@ -41,6 +41,22 @@ const ID_BASE = 1_000_000;
 const MAX_TRACKED = 2_000;
 
 let nextId = ID_BASE;
+
+/**
+ * Raise the id counter past what persistent history already holds.
+ *
+ * The counter is in-memory and restarts at ID_BASE every boot, but the
+ * ids it hands out are also the `msg_id`s written to the history table,
+ * where `INSERT OR IGNORE` + UNIQUE(chat_id, msg_id) dedupes. Without
+ * this seed, the first messages after a daemon restart re-issue ids the
+ * previous run already used — the IGNORE then silently drops them from
+ * history, and a reaction/reply addressed at an old id from history hits
+ * whatever new message reused the number. Called at frontend start with
+ * max(msg_id) over wa_* chats + 1.
+ */
+export function seedMessageStore(floor: number): void {
+  if (Number.isFinite(floor)) nextId = Math.max(nextId, Math.floor(floor));
+}
 const byMsgId = new Map<number, StoredMessage>();
 const byWaId = new Map<string, number>();
 
diff --git a/src/frontend/whatsapp/turn-recovery.ts b/src/frontend/whatsapp/turn-recovery.ts
new file mode 100644
index 000000000..d9a85a600
--- /dev/null
+++ b/src/frontend/whatsapp/turn-recovery.ts
@@ -0,0 +1,113 @@
+/**
+ * Failure semantics for a WhatsApp turn, mirroring the Telegram queue
+ * (frontend/telegram/handlers/queue.ts): a user-initiated stop settles
+ * silently, a brief transient failure gets one retry, and anything else
+ * is REPORTED IN THE CHAT. Before this existed the error went only to
+ * the log — the WhatsApp user's message was marked read and then nothing
+ * ever came back, which reads as being ignored.
+ *
+ * Split from index.ts so the policy is unit-testable without a Baileys
+ * socket: the caller injects the turn and the delivery.
+ */
+
+import {
+  classify,
+  friendlyMessage,
+  RETRY_ELAPSED_CAP_MS,
+} from "../../core/errors.js";
+import { log, logError } from "../../util/log.js";
+import {
+  recordError,
+  recordMessageProcessed,
+  recordMessageSettled,
+} from "../../util/watchdog.js";
+
+export type TurnRecoveryDeps = {
+  chatId: string;
+  senderName: string;
+  runTurn: () => Promise<unknown>;
+  /** Deliver a friendly error line into the chat. Must not throw. */
+  sendErrorText: (text: string) => Promise<void>;
+  /** Test seam for the retry pause; defaults to a real setTimeout. */
+  wait?: (ms: number) => Promise<void>;
+};
+
+export async function runTurnWithRecovery(
+  deps: TurnRecoveryDeps,
+): Promise<void> {
+  const wait =
+    deps.wait ?? ((ms: number) => new Promise<void>((r) => setTimeout(r, ms)));
+
+  const startedAt = Date.now();
+  try {
+    await deps.runTurn();
+    recordMessageProcessed();
+  } catch (err) {
+    const classified = classify(err);
+    // A user-initiated /stop is an outcome, not a fault — the stop was
+    // already acknowledged, so an error bubble here would contradict it.
+    if (classified.reason === "stopped") {
+      log("whatsapp", `[${deps.chatId}] turn stopped by user`);
+      recordMessageSettled();
+      return;
+    }
+    logError(
+      "whatsapp",
+      `[${deps.chatId}] [${deps.senderName}] ${classified.reason}: ${classified.message}`,
+    );
+    recordError(classified.message);
+
+    // Retry once for transients (rate_limit, overloaded, network) — but
+    // only when the failed attempt was brief. An attempt that already ran
+    // for minutes won't be saved by a 2s pause, and turns serialize per
+    // chat, so a blind retry doubles the stall for everything behind it.
+    const attemptMs = Date.now() - startedAt;
+    if (classified.retryable && attemptMs < RETRY_ELAPSED_CAP_MS) {
+      const delayMs = classified.retryAfterMs ?? 2000;
+      log(
+        "whatsapp",
+        `[${deps.chatId}] Retrying after ${classified.reason} (${delayMs}ms)...`,
+      );
+      try {
+        await wait(delayMs);
+        await deps.runTurn();
+        recordMessageProcessed();
+        return;
+      } catch (retryErr) {
+        const retryClassified = classify(retryErr);
+        logError(
+          "whatsapp",
+          `[${deps.chatId}] Retry failed: ${retryClassified.message}`,
+        );
+        recordMessageSettled();
+        await deps.sendErrorText(friendlyMessage(retryClassified));
+        return;
+      }
+    }
+
+    recordMessageSettled();
+    await deps.sendErrorText(friendlyMessage(classified));
+  }
+}
+
+/**
+ * How fresh a catch-up (offline-queued) message must be to still get a
+ * reply turn. Messages older than this are recorded in history — the next
+ * live turn sees them — but not answered: replying to a whole night's
+ * backlog hours later reads worse than picking up naturally.
+ */
+export const CATCH_UP_REPLY_WINDOW_MS = 15 * 60_000;
+
+/**
+ * Whether a message delivered as catch-up (Baileys `append`) should get a
+ * reply turn. `platformTsMs` is the message's own timestamp in ms; a
+ * missing/zero timestamp counts as fresh — better one odd reply than a
+ * silently dropped question.
+ */
+export function shouldReplyToCatchUp(
+  platformTsMs: number,
+  now: number = Date.now(),
+): boolean {
+  if (!Number.isFinite(platformTsMs) || platformTsMs <= 0) return true;
+  return now - platformTsMs <= CATCH_UP_REPLY_WINDOW_MS;
+}
diff --git a/src/storage/history.ts b/src/storage/history.ts
index 544f36e31..824303b11 100644
--- a/src/storage/history.ts
+++ b/src/storage/history.ts
@@ -81,6 +81,11 @@ export function pushMessage(chatId: string, msg: HistoryMessage): void {
   }
 }
 
+/** See repositories/history-repo.ts `maxMsgIdForPrefix`. */
+export function maxMsgIdForChatPrefix(prefix: string): number | undefined {
+  return repo.maxMsgIdForPrefix(prefix);
+}
+
 export function getRecentHistory(chatId: string, limit = 50): HistoryMessage[] {
   return repo.recent(chatId, limit);
 }
@@ -98,6 +103,28 @@ export function getHistoryBefore(
   return repo.recentBefore(chatId, beforeMsgId, limit);
 }
 
+/** Formatted page of the messages strictly older than `beforeMsgId`. */
+export function getFormattedBefore(
+  chatId: string,
+  beforeMsgId: number,
+  limit = 30,
+): string {
+  const messages = repo.recentBefore(chatId, beforeMsgId, limit);
+  if (messages.length === 0) return "No messages before that point.";
+  return messages.map(formatMessage).join("\n");
+}
+
+/** Formatted page of the messages strictly older than a timestamp (ms). */
+export function getFormattedBeforeTime(
+  chatId: string,
+  beforeTs: number,
+  limit = 30,
+): string {
+  const messages = repo.recentBeforeTime(chatId, beforeTs, limit);
+  if (messages.length === 0) return "No messages before that date.";
+  return messages.map(formatMessage).join("\n");
+}
+
 /**
  * Raw (wire-friendly) full-text search over a chat's history. Unlike
  * [searchHistory] — which formats a string for the agent's tool — this
diff --git a/src/storage/repositories/history-repo.ts b/src/storage/repositories/history-repo.ts
index 08d5d5f42..0df898adb 100644
--- a/src/storage/repositories/history-repo.ts
+++ b/src/storage/repositories/history-repo.ts
@@ -108,6 +108,17 @@ export function recentBefore(
   return rows.reverse().map(rowToMessage);
 }
 
+export function recentBeforeTime(
+  chatId: string,
+  beforeTs: number,
+  limit: number,
+): HistoryMessage[] {
+  const rows = getDatabase()
+    .prepare(historySql.recentBeforeTime)
+    .all(chatId, beforeTs, limit) as Row[];
+  return rows.reverse().map(rowToMessage);
+}
+
 export function setFilePath(
   chatId: string,
   msgId: number,
@@ -174,6 +185,19 @@ export function latestMsgId(chatId: string): number | undefined {
   return row?.msg_id;
 }
 
+/**
+ * Highest msg_id over every chat whose id begins with `prefix` (compared
+ * literally — LIKE wildcards in the prefix are escaped). Undefined when no
+ * such chat has any history.
+ */
+export function maxMsgIdForPrefix(prefix: string): number | undefined {
+  const pattern = prefix.replace(/[\\%_]/g, (ch) => `\\${ch}`) + "%";
+  const row = getDatabase()
+    .prepare(historySql.maxMsgIdForPrefix)
+    .get(pattern) as { max_id: number | null } | undefined;
+  return row?.max_id ?? undefined;
+}
+
 export type KnownUser = {
   senderId: number;
   name: string;
diff --git a/src/storage/sql/history.sql b/src/storage/sql/history.sql
index 5de74c0b6..5e1233370 100644
--- a/src/storage/sql/history.sql
+++ b/src/storage/sql/history.sql
@@ -21,6 +21,14 @@ SELECT msg_id, sender_id, sender_name, sender_handle, text, reply_to_msg_id,
 FROM history_messages
 WHERE chat_id = ? AND msg_id < ? ORDER BY id DESC LIMIT ?
 
+-- name: recentBeforeTime
+-- Time-cursor variant of recentBefore for the read_history `before` date
+-- parameter: the newest `limit` messages strictly older than a timestamp.
+SELECT msg_id, sender_id, sender_name, sender_handle, text, reply_to_msg_id,
+       timestamp, media_type, sticker_file_id, file_path
+FROM history_messages
+WHERE chat_id = ? AND timestamp < ? ORDER BY id DESC LIMIT ?
+
 -- name: setFilePath
 UPDATE history_messages SET file_path = ? WHERE chat_id = ? AND msg_id = ?
 
@@ -60,6 +68,12 @@ WHERE chat_id = ? AND sender_id = ? ORDER BY id DESC LIMIT ?
 -- name: latestMsgId
 SELECT msg_id FROM history_messages WHERE chat_id = ? ORDER BY id DESC LIMIT 1
 
+-- name: maxMsgIdForPrefix
+-- Highest msg_id across every chat whose id starts with a prefix
+-- (parameter is a LIKE pattern with \ escapes). Seeds the WhatsApp
+-- frontend's in-memory id counter past what history already holds.
+SELECT MAX(msg_id) AS max_id FROM history_messages WHERE chat_id LIKE ? ESCAPE '\'
+
 -- name: knownUsers
 SELECT sender_id,
        MAX(timestamp) AS last_seen,
diff --git a/src/storage/sql/statements.generated.ts b/src/storage/sql/statements.generated.ts
index f63c1075d..922438761 100644
--- a/src/storage/sql/statements.generated.ts
+++ b/src/storage/sql/statements.generated.ts
@@ -346,6 +346,12 @@ SELECT msg_id, sender_id, sender_name, sender_handle, text, reply_to_msg_id,
        timestamp, media_type, sticker_file_id, file_path
 FROM history_messages
 WHERE chat_id = ? AND msg_id < ? ORDER BY id DESC LIMIT ?`,
+  recentBeforeTime: `-- Time-cursor variant of recentBefore for the read_history \`before\` date
+-- parameter: the newest \`limit\` messages strictly older than a timestamp.
+SELECT msg_id, sender_id, sender_name, sender_handle, text, reply_to_msg_id,
+       timestamp, media_type, sticker_file_id, file_path
+FROM history_messages
+WHERE chat_id = ? AND timestamp < ? ORDER BY id DESC LIMIT ?`,
   setFilePath: `UPDATE history_messages SET file_path = ? WHERE chat_id = ? AND msg_id = ?`,
   deleteChat: `DELETE FROM history_messages WHERE chat_id = ?`,
   searchFts: `-- The match param must already be a valid FTS5 expression
@@ -371,6 +377,10 @@ WHERE chat_id = ? AND msg_id = ? ORDER BY id DESC LIMIT 1`,
 FROM history_messages
 WHERE chat_id = ? AND sender_id = ? ORDER BY id DESC LIMIT ?`,
   latestMsgId: `SELECT msg_id FROM history_messages WHERE chat_id = ? ORDER BY id DESC LIMIT 1`,
+  maxMsgIdForPrefix: `-- Highest msg_id across every chat whose id starts with a prefix
+-- (parameter is a LIKE pattern with \\ escapes). Seeds the WhatsApp
+-- frontend's in-memory id counter past what history already holds.
+SELECT MAX(msg_id) AS max_id FROM history_messages WHERE chat_id LIKE ? ESCAPE '\\'`,
   knownUsers: `SELECT sender_id,
        MAX(timestamp) AS last_seen,
        COUNT(*) AS message_count,