diff --git a/CHANGELOG.md b/CHANGELOG.md
index c20a8f58c53..4ef32c766b5 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -27,6 +27,7 @@ Docs: https://docs.openclaw.ai
 - Agents/CLI transcripts: persist successful CLI-backed turns into the OpenClaw session transcript so google-gemini-cli replies appear in session history and the Control UI again. (#67490) Thanks @obviyus.
 - Discord/tool-call text: strip standalone Gemma-style `<function>...</function>` tool-call payloads from visible assistant text without truncating prose examples or trailing replies. (#67318) Thanks @joelnishanth.
 - WhatsApp/web-session: drain the pending per-auth creds save queue before reopening sockets so reconnect-time auth bootstrap no longer races in-flight `creds.json` writes and falsely restores from backup. (#67464) Thanks @neeravmakwana.
+- BlueBubbles/catchup: add a per-message retry ceiling (`catchup.maxFailureRetries`, default 10) so a persistently-failing message with a malformed payload no longer wedges the catchup cursor forever. After N consecutive `processMessage` failures against the same GUID, catchup logs a WARN, skips that message on subsequent sweeps, and lets the cursor advance past it. Transient failures still retry from the same point as before. Also fixes a lost-update race in the persistent dedupe file lock that silently dropped inbound GUIDs on concurrent writes, a dedupe file naming migration gap on version upgrade, and a balloon-event bypass that let catchup replay debouncer-coalesced events as standalone messages. (#67426, #66870) Thanks @omarshahine.
 
 ## 2026.4.15-beta.1
 
diff --git a/extensions/bluebubbles/src/catchup.test.ts b/extensions/bluebubbles/src/catchup.test.ts
index a87818bdf87..7e4a265dea7 100644
--- a/extensions/bluebubbles/src/catchup.test.ts
+++ b/extensions/bluebubbles/src/catchup.test.ts
@@ -428,9 +428,13 @@ describe("runBlueBubblesCatchup", () => {
     // Cursor is held just before the bad message's timestamp so the next
     // sweep retries it (and re-queries ok1 which dedupe will drop).
     expect(summary?.failed).toBe(1);
+    expect(summary?.givenUp).toBe(0);
     expect(summary?.cursorAfter).toBe(7 * 60 * 1000 - 1);
     const cursorAfter = await loadBlueBubblesCatchupCursor("test-account");
     expect(cursorAfter?.lastSeenMs).toBe(7 * 60 * 1000 - 1);
+    // Retry counter is persisted so subsequent sweeps know how close we
+    // are to the give-up ceiling.
+    expect(cursorAfter?.failureRetries?.bad).toBe(1);
   });
 
   it("clamps held cursor to previous cursor when failure ts is below it", async () => {
@@ -606,6 +610,494 @@ describe("runBlueBubblesCatchup", () => {
   });
 });
 
+describe("runBlueBubblesCatchup — per-message retry cap", () => {
+  let stateDir: string;
+  beforeEach(() => {
+    stateDir = makeStateDir();
+  });
+  afterEach(() => {
+    clearStateDir(stateDir);
+    vi.restoreAllMocks();
+  });
+
+  it("increments retry counter on each consecutive failure and holds cursor", async () => {
+    // Three sweeps, all fail on the same GUID. Counter accumulates and
+    // cursor stays pinned below the failing message so every sweep
+    // retries it. maxFailureRetries: 5 so we don't give up inside this
+    // test.
+    const now1 = 10 * 60 * 1000;
+    const now2 = now1 + 60 * 1000;
+    const now3 = now2 + 60 * 1000;
+    await saveBlueBubblesCatchupCursor("test-account", 5 * 60 * 1000);
+
+    const target = makeTarget({
+      account: {
+        accountId: "test-account",
+        enabled: true,
+        configured: true,
+        baseUrl: "http://127.0.0.1:1234",
+        config: {
+          serverUrl: "http://127.0.0.1:1234",
+          password: "x",
+          network: { dangerouslyAllowPrivateNetwork: true },
+          catchup: { maxFailureRetries: 5 },
+        } as unknown as WebhookTarget["account"]["config"],
+      },
+    });
+
+    const fetchMessages = async () => ({
+      resolved: true,
+      messages: [makeBbMessage({ guid: "wedge", dateCreated: 7 * 60 * 1000 })],
+    });
+    const processMessageFn = async () => {
+      throw new Error("boom");
+    };
+
+    const s1 = await runBlueBubblesCatchup(target, {
+      now: () => now1,
+      fetchMessages,
+      processMessageFn,
+    });
+    const s2 = await runBlueBubblesCatchup(target, {
+      now: () => now2,
+      fetchMessages,
+      processMessageFn,
+    });
+    const s3 = await runBlueBubblesCatchup(target, {
+      now: () => now3,
+      fetchMessages,
+      processMessageFn,
+    });
+
+    expect(s1?.failed).toBe(1);
+    expect(s1?.givenUp).toBe(0);
+    expect(s2?.givenUp).toBe(0);
+    expect(s3?.givenUp).toBe(0);
+    const cursor = await loadBlueBubblesCatchupCursor("test-account");
+    expect(cursor?.failureRetries?.wedge).toBe(3);
+    // Cursor still held just below the wedge message's timestamp.
+    expect(cursor?.lastSeenMs).toBe(7 * 60 * 1000 - 1);
+  });
+
+  it("gives up on the Nth consecutive failure and records count >= max", async () => {
+    const now = 10 * 60 * 1000;
+    await saveBlueBubblesCatchupCursor("test-account", 5 * 60 * 1000);
+    // Pre-seed a cursor with retries at the one-before-give-up threshold
+    // so a single run trips the ceiling. This mirrors what would happen
+    // after many runs through the incremental-retry path above.
+    await saveBlueBubblesCatchupCursor("test-account", 5 * 60 * 1000, { wedge: 2 });
+
+    const warnings: string[] = [];
+    const target = makeTarget({
+      account: {
+        accountId: "test-account",
+        enabled: true,
+        configured: true,
+        baseUrl: "http://127.0.0.1:1234",
+        config: {
+          serverUrl: "http://127.0.0.1:1234",
+          password: "x",
+          network: { dangerouslyAllowPrivateNetwork: true },
+          catchup: { maxFailureRetries: 3 },
+        } as unknown as WebhookTarget["account"]["config"],
+      },
+    });
+
+    const summary = await runBlueBubblesCatchup(target, {
+      now: () => now,
+      fetchMessages: async () => ({
+        resolved: true,
+        messages: [makeBbMessage({ guid: "wedge", dateCreated: 7 * 60 * 1000 })],
+      }),
+      processMessageFn: async () => {
+        throw new Error("malformed");
+      },
+      error: (m) => warnings.push(m),
+    });
+
+    expect(summary?.failed).toBe(1);
+    expect(summary?.givenUp).toBe(1);
+    // Give-up no longer holds the cursor: it advances to nowMs so the
+    // wedge message falls out of the next query window entirely.
+    expect(summary?.cursorAfter).toBe(now);
+
+    const persisted = await loadBlueBubblesCatchupCursor("test-account");
+    expect(persisted?.lastSeenMs).toBe(now);
+    // Counter is persisted at the give-up value so a later sweep that
+    // still sees the message (e.g., because a different GUID is holding
+    // the cursor) will recognize the GUID as given up and skip it.
+    expect(persisted?.failureRetries?.wedge).toBe(3);
+
+    // Distinct WARN log line fired on the give-up transition.
+    const giveUpWarnings = warnings.filter((w) => w.includes("giving up on guid="));
+    expect(giveUpWarnings).toHaveLength(1);
+    expect(giveUpWarnings[0]).toContain("guid=wedge");
+    expect(giveUpWarnings[0]).toContain("3 consecutive failures");
+  });
+
+  it("skips an already-given-up GUID without re-attempting processMessage", async () => {
+    // Setup: the cursor file was written with wedge already at the
+    // give-up threshold from a prior run. On this run, the cursor is
+    // held by a different, still-retrying GUID (`held`), so wedge's
+    // timestamp falls back into the query window. Catchup must skip
+    // wedge without invoking processMessage on it.
+    const now = 10 * 60 * 1000;
+    await saveBlueBubblesCatchupCursor("test-account", 5 * 60 * 1000, { wedge: 3 });
+
+    const attempted: string[] = [];
+    const target = makeTarget({
+      account: {
+        accountId: "test-account",
+        enabled: true,
+        configured: true,
+        baseUrl: "http://127.0.0.1:1234",
+        config: {
+          serverUrl: "http://127.0.0.1:1234",
+          password: "x",
+          network: { dangerouslyAllowPrivateNetwork: true },
+          catchup: { maxFailureRetries: 3 },
+        } as unknown as WebhookTarget["account"]["config"],
+      },
+    });
+
+    const summary = await runBlueBubblesCatchup(target, {
+      now: () => now,
+      fetchMessages: async () => ({
+        resolved: true,
+        messages: [
+          makeBbMessage({ guid: "held", dateCreated: 6 * 60 * 1000 }),
+          makeBbMessage({ guid: "wedge", dateCreated: 7 * 60 * 1000 }),
+        ],
+      }),
+      processMessageFn: async (m) => {
+        attempted.push(m.messageId ?? "?");
+        if (m.messageId === "held") {
+          throw new Error("transient");
+        }
+      },
+    });
+
+    // processMessage never runs for wedge.
+    expect(attempted).toEqual(["held"]);
+    expect(summary?.skippedGivenUp).toBe(1);
+    expect(summary?.failed).toBe(1);
+    expect(summary?.givenUp).toBe(0);
+    // Cursor held at `held` so held keeps retrying next sweep.
+    expect(summary?.cursorAfter).toBe(6 * 60 * 1000 - 1);
+
+    const cursor = await loadBlueBubblesCatchupCursor("test-account");
+    // Both entries preserved: held at count 1 (still retrying),
+    // wedge at count 3 (given up, sticky).
+    expect(cursor?.failureRetries?.held).toBe(1);
+    expect(cursor?.failureRetries?.wedge).toBe(3);
+  });
+
+  it("clears the retry counter on successful processing", async () => {
+    // GUID recovered after a transient failure. The counter must drop
+    // so the next failure starts fresh (not carrying forward stale
+    // retry history).
+    const now = 10 * 60 * 1000;
+    await saveBlueBubblesCatchupCursor("test-account", 5 * 60 * 1000, { flaky: 4 });
+
+    const summary = await runBlueBubblesCatchup(makeTarget(), {
+      now: () => now,
+      fetchMessages: async () => ({
+        resolved: true,
+        messages: [makeBbMessage({ guid: "flaky", dateCreated: 6 * 60 * 1000 })],
+      }),
+      processMessageFn: async () => {
+        /* succeeds */
+      },
+    });
+
+    expect(summary?.replayed).toBe(1);
+    const cursor = await loadBlueBubblesCatchupCursor("test-account");
+    expect(cursor?.failureRetries?.flaky).toBeUndefined();
+    // When the map is empty, the field itself is omitted from the file.
+    expect(cursor?.failureRetries).toBeUndefined();
+    expect(cursor?.lastSeenMs).toBe(now);
+  });
+
+  it("resolves 'earlier retry + later give-up' by holding cursor at earlier and skipping later", async () => {
+    // This is the key scenario issue #66870 exists to solve. GUID A at
+    // t=6min is still retrying (count=1). GUID B at t=7min has been
+    // failing for many runs and crosses the ceiling on this run. The
+    // wrong answer is "advance cursor past B to t=7min" — that would
+    // lose A. The right answer is "hold cursor below A, record B as
+    // given-up, skip B on sight next run".
+    const now = 10 * 60 * 1000;
+    await saveBlueBubblesCatchupCursor("test-account", 5 * 60 * 1000, { giveUpHere: 2 });
+
+    const target = makeTarget({
+      account: {
+        accountId: "test-account",
+        enabled: true,
+        configured: true,
+        baseUrl: "http://127.0.0.1:1234",
+        config: {
+          serverUrl: "http://127.0.0.1:1234",
+          password: "x",
+          network: { dangerouslyAllowPrivateNetwork: true },
+          catchup: { maxFailureRetries: 3 },
+        } as unknown as WebhookTarget["account"]["config"],
+      },
+    });
+
+    const summary = await runBlueBubblesCatchup(target, {
+      now: () => now,
+      fetchMessages: async () => ({
+        resolved: true,
+        messages: [
+          makeBbMessage({ guid: "retryEarlier", dateCreated: 6 * 60 * 1000 }),
+          makeBbMessage({ guid: "giveUpHere", dateCreated: 7 * 60 * 1000 }),
+        ],
+      }),
+      processMessageFn: async () => {
+        throw new Error("failing");
+      },
+    });
+
+    expect(summary?.failed).toBe(2);
+    expect(summary?.givenUp).toBe(1);
+    // Cursor held at (earlier message ts - 1) so retryEarlier keeps retrying.
+    expect(summary?.cursorAfter).toBe(6 * 60 * 1000 - 1);
+
+    const cursor = await loadBlueBubblesCatchupCursor("test-account");
+    expect(cursor?.failureRetries?.retryEarlier).toBe(1);
+    // Give-up counter preserved at or above the threshold.
+    expect(cursor?.failureRetries?.giveUpHere).toBe(3);
+  });
+
+  it("uses the default retry cap when maxFailureRetries is omitted from config", async () => {
+    // Boot-strap: record 9 failures, then a 10th should trigger give-up
+    // at the default threshold. We pre-seed the counter at 9 so this
+    // single-run test doesn't need to iterate the whole sequence.
+    const now = 10 * 60 * 1000;
+    await saveBlueBubblesCatchupCursor("test-account", 5 * 60 * 1000, { wedge: 9 });
+
+    const warnings: string[] = [];
+    const summary = await runBlueBubblesCatchup(makeTarget(), {
+      now: () => now,
+      fetchMessages: async () => ({
+        resolved: true,
+        messages: [makeBbMessage({ guid: "wedge", dateCreated: 6 * 60 * 1000 })],
+      }),
+      processMessageFn: async () => {
+        throw new Error("boom");
+      },
+      error: (m) => warnings.push(m),
+    });
+    expect(summary?.givenUp).toBe(1);
+    expect(warnings.some((w) => w.includes("giving up on guid=wedge"))).toBe(true);
+    expect(warnings.some((w) => w.includes("10 consecutive failures"))).toBe(true);
+  });
+
+  it("clamps maxFailureRetries to >= 1 when configured to zero or negative", async () => {
+    // With clamp floor of 1, the first failure already meets count >= 1
+    // so catchup gives up immediately on first attempt.
+    const now = 10 * 60 * 1000;
+    await saveBlueBubblesCatchupCursor("test-account", 5 * 60 * 1000);
+
+    const summary = await runBlueBubblesCatchup(
+      makeTarget({
+        account: {
+          accountId: "test-account",
+          enabled: true,
+          configured: true,
+          baseUrl: "http://127.0.0.1:1234",
+          config: {
+            serverUrl: "http://127.0.0.1:1234",
+            password: "x",
+            network: { dangerouslyAllowPrivateNetwork: true },
+            catchup: { maxFailureRetries: 0 },
+          } as unknown as WebhookTarget["account"]["config"],
+        },
+      }),
+      {
+        now: () => now,
+        fetchMessages: async () => ({
+          resolved: true,
+          messages: [makeBbMessage({ guid: "wedge", dateCreated: 6 * 60 * 1000 })],
+        }),
+        processMessageFn: async () => {
+          throw new Error("boom");
+        },
+      },
+    );
+    expect(summary?.givenUp).toBe(1);
+    expect(summary?.cursorAfter).toBe(now);
+  });
+
+  it("loads cleanly from a legacy cursor file without a failureRetries field", async () => {
+    // Older cursor files (written before this field existed) must still
+    // parse. Round-trip: save without the field (legacy path), then
+    // run catchup and confirm a normal sweep proceeds.
+    await saveBlueBubblesCatchupCursor("test-account", 5 * 60 * 1000);
+    const loaded = await loadBlueBubblesCatchupCursor("test-account");
+    expect(loaded?.lastSeenMs).toBe(5 * 60 * 1000);
+    expect(loaded?.failureRetries).toBeUndefined();
+
+    const summary = await runBlueBubblesCatchup(makeTarget(), {
+      now: () => 10 * 60 * 1000,
+      fetchMessages: async () => ({
+        resolved: true,
+        messages: [makeBbMessage({ guid: "ok", dateCreated: 6 * 60 * 1000 })],
+      }),
+      processMessageFn: async () => {},
+    });
+    expect(summary?.replayed).toBe(1);
+  });
+
+  it("drops retry entries for GUIDs that are no longer in the query window", async () => {
+    // A stale entry carried in the cursor file (e.g., from an older
+    // run whose cursor has since advanced past its timestamp) should
+    // NOT be carried forward if the GUID does not appear in the
+    // current fetch. Otherwise the map grows without bound over time.
+    const now = 10 * 60 * 1000;
+    await saveBlueBubblesCatchupCursor("test-account", 5 * 60 * 1000, {
+      staleGuid: 2,
+      alsoStale: 5,
+    });
+
+    const summary = await runBlueBubblesCatchup(makeTarget(), {
+      now: () => now,
+      fetchMessages: async () => ({
+        resolved: true,
+        // Fetch returns entirely different GUIDs from the stored map.
+        messages: [makeBbMessage({ guid: "fresh", dateCreated: 6 * 60 * 1000 })],
+      }),
+      processMessageFn: async () => {},
+    });
+    expect(summary?.replayed).toBe(1);
+    const cursor = await loadBlueBubblesCatchupCursor("test-account");
+    // Both stale entries dropped; no new entries since the fresh message
+    // succeeded.
+    expect(cursor?.failureRetries).toBeUndefined();
+  });
+
+  it("preserves stickiness when a given-up GUID reappears and fails again", async () => {
+    // Setup: cursor advanced, but held by a newer still-retrying GUID
+    // `held`. The wedge GUID is already given up from a prior run and
+    // still appears because `held` is holding the cursor below it.
+    // Catchup must continue to skip wedge on sight across many runs
+    // without ever calling processMessage on it.
+    const now = 10 * 60 * 1000;
+    await saveBlueBubblesCatchupCursor("test-account", 5 * 60 * 1000, {
+      wedge: 10,
+      held: 1,
+    });
+
+    const attempted: string[] = [];
+    const target = makeTarget({
+      account: {
+        accountId: "test-account",
+        enabled: true,
+        configured: true,
+        baseUrl: "http://127.0.0.1:1234",
+        config: {
+          serverUrl: "http://127.0.0.1:1234",
+          password: "x",
+          network: { dangerouslyAllowPrivateNetwork: true },
+          catchup: { maxFailureRetries: 5 },
+        } as unknown as WebhookTarget["account"]["config"],
+      },
+    });
+    const fetchMessages = async () => ({
+      resolved: true,
+      messages: [
+        makeBbMessage({ guid: "held", dateCreated: 6 * 60 * 1000 }),
+        makeBbMessage({ guid: "wedge", dateCreated: 7 * 60 * 1000 }),
+      ],
+    });
+    const processMessageFn = async () => {
+      throw new Error("still broken");
+    };
+
+    for (let i = 0; i < 3; i++) {
+      await runBlueBubblesCatchup(target, {
+        now: () => now + i,
+        fetchMessages,
+        processMessageFn: async (m) => {
+          attempted.push(m.messageId ?? "?");
+          return processMessageFn();
+        },
+      });
+    }
+    // wedge is NEVER attempted despite reappearing every sweep.
+    expect(attempted.filter((g) => g === "wedge")).toHaveLength(0);
+    // held is attempted every sweep.
+    expect(attempted.filter((g) => g === "held")).toHaveLength(3);
+  });
+
+  it("summary.skippedGivenUp counter is zero on a clean run", async () => {
+    const summary = await runBlueBubblesCatchup(makeTarget(), {
+      now: () => 10_000,
+      fetchMessages: async () => ({ resolved: true, messages: [] }),
+      processMessageFn: async () => {},
+    });
+    expect(summary?.skippedGivenUp).toBe(0);
+    expect(summary?.givenUp).toBe(0);
+  });
+});
+
+describe("saveBlueBubblesCatchupCursor + loadBlueBubblesCatchupCursor — retry map", () => {
+  let stateDir: string;
+  beforeEach(() => {
+    stateDir = makeStateDir();
+  });
+  afterEach(() => {
+    clearStateDir(stateDir);
+  });
+
+  it("round-trips an empty retry map by omitting the field from the persisted shape", async () => {
+    await saveBlueBubblesCatchupCursor("acct", 100, {});
+    const loaded = await loadBlueBubblesCatchupCursor("acct");
+    expect(loaded?.lastSeenMs).toBe(100);
+    expect(loaded?.failureRetries).toBeUndefined();
+  });
+
+  it("round-trips a populated retry map", async () => {
+    await saveBlueBubblesCatchupCursor("acct", 100, { a: 1, b: 9 });
+    const loaded = await loadBlueBubblesCatchupCursor("acct");
+    expect(loaded?.failureRetries).toEqual({ a: 1, b: 9 });
+  });
+
+  it("filters malformed retry entries during load (zero, negative, non-numeric)", async () => {
+    // Use the public save to produce the on-disk file, then overwrite
+    // its contents with a hand-crafted payload to exercise the loader's
+    // sanitization independently of what the saver would emit.
+    await saveBlueBubblesCatchupCursor("acct", 100);
+    const stateRoot = process.env.OPENCLAW_STATE_DIR;
+    if (!stateRoot) {
+      throw new Error("OPENCLAW_STATE_DIR must be set by the test harness");
+    }
+    const dir = path.join(stateRoot, "bluebubbles", "catchup");
+    const files = fs.readdirSync(dir);
+    expect(files).toHaveLength(1);
+    const firstFile = files[0];
+    if (!firstFile) {
+      throw new Error("expected a cursor file to exist after save");
+    }
+    const badCursor = {
+      lastSeenMs: 100,
+      updatedAt: 0,
+      failureRetries: {
+        good: 3,
+        zero: 0,
+        negative: -1,
+        notANumber: "oops",
+        infinite: Number.POSITIVE_INFINITY,
+        nan: Number.NaN,
+      },
+    };
+    fs.writeFileSync(path.join(dir, firstFile), JSON.stringify(badCursor));
+
+    const loaded = await loadBlueBubblesCatchupCursor("acct");
+    expect(loaded?.lastSeenMs).toBe(100);
+    expect(loaded?.failureRetries).toEqual({ good: 3 });
+  });
+});
+
 describe("fetchBlueBubblesMessagesSince", () => {
   it("returns resolved:false when the network call throws", async () => {
     // Point at a port nothing is listening on so fetch fails fast.
diff --git a/extensions/bluebubbles/src/catchup.ts b/extensions/bluebubbles/src/catchup.ts
index 3c1aba299be..0aa70342264 100644
--- a/extensions/bluebubbles/src/catchup.ts
+++ b/extensions/bluebubbles/src/catchup.ts
@@ -4,6 +4,7 @@ import { readJsonFileWithFallback, writeJsonFileAtomically } from "openclaw/plug
 import { resolveStateDir } from "openclaw/plugin-sdk/state-paths";
 import { resolvePreferredOpenClawTmpDir } from "openclaw/plugin-sdk/temp-path";
 import { resolveBlueBubblesServerAccount } from "./account-resolve.js";
+import { warmupBlueBubblesInboundDedupe } from "./inbound-dedupe.js";
 import { asRecord, normalizeWebhookMessage } from "./monitor-normalize.js";
 import { processMessage } from "./monitor-processing.js";
 import type { WebhookTarget } from "./monitor-shared.js";
@@ -21,6 +22,14 @@ const MAX_MAX_AGE_MINUTES = 12 * 60;
 const DEFAULT_PER_RUN_LIMIT = 50;
 const MAX_PER_RUN_LIMIT = 500;
 const DEFAULT_FIRST_RUN_LOOKBACK_MINUTES = 30;
+const DEFAULT_MAX_FAILURE_RETRIES = 10;
+const MAX_MAX_FAILURE_RETRIES = 1_000;
+// Defense-in-depth bound: a runaway retry map (e.g., a storm of unique
+// failing GUIDs) should not balloon the cursor file unboundedly. When the
+// map exceeds this size, we keep only the highest-count entries (the ones
+// closest to being given up) and drop the rest. Realistic backlogs stay
+// well under this; the bound exists to cap pathological growth.
+const MAX_FAILURE_RETRY_MAP_SIZE = 5_000;
 const FETCH_TIMEOUT_MS = 15_000;
 
 export type BlueBubblesCatchupConfig = {
@@ -28,6 +37,13 @@ export type BlueBubblesCatchupConfig = {
   maxAgeMinutes?: number;
   perRunLimit?: number;
   firstRunLookbackMinutes?: number;
+  /**
+   * Per-message retry ceiling. After this many consecutive failed
+   * `processMessage` attempts against the same GUID, catchup logs a WARN
+   * and force-advances the cursor past the wedged message instead of
+   * holding it indefinitely. Defaults to 10. Clamped to [1, 1000].
+   */
+  maxFailureRetries?: number;
 };
 
 export type BlueBubblesCatchupSummary = {
@@ -35,7 +51,21 @@ export type BlueBubblesCatchupSummary = {
   replayed: number;
   skippedFromMe: number;
   skippedPreCursor: number;
+  /**
+   * Messages whose GUID was already recorded as "given up" from a previous
+   * run (count >= `maxFailureRetries`). These are skipped without calling
+   * `processMessage` again. Lets the cursor continue advancing past the
+   * wedged message on the next sweep while avoiding another failed attempt.
+   */
+  skippedGivenUp: number;
   failed: number;
+  /**
+   * Messages that crossed the `maxFailureRetries` ceiling ON THIS RUN.
+   * Each transition triggers a WARN log line. Already-given-up messages
+   * in subsequent runs count under `skippedGivenUp`, not here. Lets
+   * operators distinguish fresh give-up events from steady-state skips.
+   */
+  givenUp: number;
   cursorBefore: number | null;
   cursorAfter: number;
   windowStartMs: number;
@@ -43,7 +73,24 @@ export type BlueBubblesCatchupSummary = {
   fetchedCount: number;
 };
 
-export type BlueBubblesCatchupCursor = { lastSeenMs: number; updatedAt: number };
+export type BlueBubblesCatchupCursor = {
+  lastSeenMs: number;
+  updatedAt: number;
+  /**
+   * Per-GUID failure counter, preserved across runs. Two states:
+   * - `1 <= count < maxFailureRetries`: the GUID is still retrying and
+   *   continues to hold the cursor back.
+   * - `count >= maxFailureRetries`: catchup has "given up" on the GUID.
+   *   The message is skipped on sight (no `processMessage` attempt) and
+   *   the GUID no longer holds the cursor. The entry stays in the map
+   *   until the cursor naturally advances past the message's timestamp
+   *   (at which point the message stops appearing in queries entirely).
+   *
+   * A successful `processMessage` removes the entry. Optional on the
+   * persisted shape so older cursor files without this field load cleanly.
+   */
+  failureRetries?: Record<string, number>;
+};
 
 function resolveStateDirFromEnv(env: NodeJS.ProcessEnv = process.env): string {
   // Explicit OPENCLAW_STATE_DIR overrides take precedence (including
@@ -81,6 +128,26 @@ function resolveCursorFilePath(accountId: string): string {
   );
 }
 
+function sanitizeFailureRetriesInput(raw: unknown): Record<string, number> {
+  // Older cursor files don't carry this field; also guard against
+  // hand-edited JSON or future shape drift. Drop any entry whose count is
+  // not a finite positive integer so downstream arithmetic stays sound.
+  if (!raw || typeof raw !== "object") {
+    return {};
+  }
+  const out: Record<string, number> = {};
+  for (const [guid, count] of Object.entries(raw as Record<string, unknown>)) {
+    if (!guid || typeof guid !== "string") {
+      continue;
+    }
+    if (typeof count !== "number" || !Number.isFinite(count) || count <= 0) {
+      continue;
+    }
+    out[guid] = Math.floor(count);
+  }
+  return out;
+}
+
 export async function loadBlueBubblesCatchupCursor(
   accountId: string,
 ): Promise<BlueBubblesCatchupCursor | null> {
@@ -92,18 +159,66 @@ export async function loadBlueBubblesCatchupCursor(
   if (typeof value.lastSeenMs !== "number" || !Number.isFinite(value.lastSeenMs)) {
     return null;
   }
-  return value;
+  const failureRetries = sanitizeFailureRetriesInput(value.failureRetries);
+  const hasRetries = Object.keys(failureRetries).length > 0;
+  // Keep the shape consistent with what the writer emits: only carry the
+  // `failureRetries` key when there's something to retry. Old cursor files
+  // without the field continue to round-trip to the same shape.
+  return {
+    lastSeenMs: value.lastSeenMs,
+    updatedAt: typeof value.updatedAt === "number" ? value.updatedAt : 0,
+    ...(hasRetries ? { failureRetries } : {}),
+  };
 }
 
 export async function saveBlueBubblesCatchupCursor(
   accountId: string,
   lastSeenMs: number,
+  failureRetries?: Record<string, number>,
 ): Promise<void> {
   const filePath = resolveCursorFilePath(accountId);
-  const cursor: BlueBubblesCatchupCursor = { lastSeenMs, updatedAt: Date.now() };
+  const sanitized = sanitizeFailureRetriesInput(failureRetries);
+  const hasRetries = Object.keys(sanitized).length > 0;
+  const cursor: BlueBubblesCatchupCursor = {
+    lastSeenMs,
+    updatedAt: Date.now(),
+    // Only emit the field when non-empty so unrelated cursor writes from
+    // the happy path don't bloat the cursor file with `"failureRetries": {}`.
+    ...(hasRetries ? { failureRetries: sanitized } : {}),
+  };
   await writeJsonFileAtomically(filePath, cursor);
 }
 
+/**
+ * Bound the retry map so a pathological storm of unique failing GUIDs
+ * cannot grow the cursor file without limit. Keeps the `maxSize` entries
+ * with the highest counts (closest to give-up) when over the bound.
+ *
+ * The map is already scoped to "currently failing, still-retrying" GUIDs
+ * and prunes on every run (entries not observed in the fetched window are
+ * dropped), so this is a defense-in-depth cap, not the primary pruning
+ * mechanism.
+ */
+function capFailureRetriesMap(
+  map: Record<string, number>,
+  maxSize: number,
+): Record<string, number> {
+  const entries = Object.entries(map);
+  if (entries.length <= maxSize) {
+    return map;
+  }
+  // Sort by count desc; stable tiebreak on guid string so the retained set
+  // is deterministic across runs (important for cursor-file diffing during
+  // debugging).
+  entries.sort((a, b) => b[1] - a[1] || a[0].localeCompare(b[0]));
+  const capped: Record<string, number> = {};
+  for (let i = 0; i < maxSize; i++) {
+    const [guid, count] = entries[i];
+    capped[guid] = count;
+  }
+  return capped;
+}
+
 type FetchOpts = {
   baseUrl: string;
   password: string;
@@ -180,10 +295,15 @@ function clampCatchupConfig(raw?: BlueBubblesCatchupConfig) {
     Math.max(raw?.firstRunLookbackMinutes ?? DEFAULT_FIRST_RUN_LOOKBACK_MINUTES, 1),
     MAX_MAX_AGE_MINUTES,
   );
+  const maxFailureRetries = Math.min(
+    Math.max(Math.floor(raw?.maxFailureRetries ?? DEFAULT_MAX_FAILURE_RETRIES), 1),
+    MAX_MAX_FAILURE_RETRIES,
+  );
   return {
     maxAgeMs: maxAgeMinutes * 60_000,
     perRunLimit,
     firstRunLookbackMs: firstRunLookbackMinutes * 60_000,
+    maxFailureRetries,
   };
 }
 
@@ -247,10 +367,11 @@ async function runBlueBubblesCatchupInner(
   const procFn = deps.processMessageFn ?? processMessage;
   const accountId = target.account.accountId;
 
-  const { maxAgeMs, perRunLimit, firstRunLookbackMs } = clampCatchupConfig(raw);
+  const { maxAgeMs, perRunLimit, firstRunLookbackMs, maxFailureRetries } = clampCatchupConfig(raw);
   const nowMs = now();
   const existing = await loadBlueBubblesCatchupCursor(accountId).catch(() => null);
   const cursorBefore = existing?.lastSeenMs ?? null;
+  const prevRetries = existing?.failureRetries ?? {};
 
   // Catchup runs once per gateway startup (called from monitor.ts after
   // webhook target registration). We deliberately do NOT short-circuit on
@@ -295,6 +416,15 @@ async function runBlueBubblesCatchupInner(
     return null;
   }
 
+  // Ensure legacy→hashed dedupe file migration runs and the on-disk store
+  // is warm before we replay. Without this, an upgrade from a version that
+  // used the old `${safe}.json` naming to the current `${safe}__${hash}.json`
+  // would start with an empty dedupe cache and re-dispatch every message in
+  // the catchup window — producing duplicate replies.
+  await warmupBlueBubblesInboundDedupe(accountId).catch((err) => {
+    error?.(`[${accountId}] BlueBubbles catchup: dedupe warmup failed: ${String(err)}`);
+  });
+
   const { resolved, messages } = await fetchFn(windowStartMs, perRunLimit, {
     baseUrl,
     password,
@@ -306,7 +436,9 @@ async function runBlueBubblesCatchupInner(
     replayed: 0,
     skippedFromMe: 0,
     skippedPreCursor: 0,
+    skippedGivenUp: 0,
     failed: 0,
+    givenUp: 0,
     cursorBefore,
     cursorAfter: nowMs,
     windowStartMs,
@@ -320,18 +452,31 @@ async function runBlueBubblesCatchupInner(
     return summary;
   }
 
-  // Track the earliest timestamp where `processMessage` threw so we never
-  // advance the cursor past a retryable failure. Normalize failures (the
-  // record didn't yield a usable NormalizedWebhookMessage) are treated as
-  // permanent skips and do NOT block cursor advance — those payloads are
-  // unlikely to ever normalize on retry, and blocking on them would wedge
-  // catchup forever.
+  // Track the earliest timestamp where `processMessage` threw *and* the
+  // failing message has not yet crossed the per-GUID retry ceiling, so we
+  // never advance the cursor past a retryable failure. Normalize failures
+  // (the record didn't yield a usable NormalizedWebhookMessage) are
+  // treated as permanent skips and do NOT block cursor advance — those
+  // payloads are unlikely to ever normalize on retry, and blocking on
+  // them would wedge catchup forever. Given-up messages (count >= max)
+  // also do NOT contribute here; see `skippedGivenUp` below.
   let earliestProcessFailureTs: number | null = null;
   // Track the latest fetched message timestamp regardless of fate, so a
   // truncated query (fetchedCount === perRunLimit) can advance the cursor
   // exactly to the page boundary. Without this, the unfetched tail past
   // the cap is permanently unreachable.
   let latestFetchedTs = windowStartMs;
+  // Next-run retry map. Built from scratch each run so entries for GUIDs
+  // that didn't appear in this fetch are dropped (the cursor has
+  // advanced past them and they will never be queried again). Entries we
+  // do carry forward encode two states via the stored count:
+  // - `1 <= count < maxFailureRetries`: still-retrying, holds cursor.
+  // - `count >= maxFailureRetries`: given-up, skipped on sight without
+  //   another `processMessage` attempt. Preserving the count is what
+  //   keeps the give-up state sticky across runs when an earlier
+  //   still-retrying failure is holding the cursor and the given-up
+  //   message keeps reappearing in the query window.
+  const nextRetries: Record<string, number> = {};
 
   for (const rec of messages) {
     // Defense in depth: the server-side `after:` filter should already
@@ -353,6 +498,30 @@ async function runBlueBubblesCatchupInner(
       continue;
     }
 
+    // Skip tapback/reaction/balloon events. These carry an
+    // `associatedMessageGuid` pointing at the parent text message and
+    // have a different `guid` of their own. The live webhook path handles
+    // balloons via the debouncer, which coalesces them with their parent.
+    // Without debouncing here, replaying a balloon would dispatch it as a
+    // standalone message — producing a duplicate reply to the parent.
+    //
+    // Guard: only skip when `associatedMessageType` is set (tapbacks and
+    // reactions — e.g., "like", 2000) OR `balloonBundleId` is set (URL
+    // previews, stickers). iMessage threaded replies use a separate
+    // `threadOriginatorGuid` field and do NOT set either of these, so
+    // they pass through for correct catchup replay.
+    const assocGuid =
+      typeof rec.associatedMessageGuid === "string"
+        ? rec.associatedMessageGuid.trim()
+        : typeof rec.associated_message_guid === "string"
+          ? rec.associated_message_guid.trim()
+          : "";
+    const assocType = rec.associatedMessageType ?? rec.associated_message_type;
+    const balloonId = typeof rec.balloonBundleId === "string" ? rec.balloonBundleId.trim() : "";
+    if (assocGuid && (assocType != null || balloonId)) {
+      continue;
+    }
+
     const normalized = normalizeWebhookMessage({ type: "new-message", data: rec });
     if (!normalized) {
       summary.failed++;
@@ -363,15 +532,62 @@ async function runBlueBubblesCatchupInner(
       continue;
     }
 
+    // Prefer the normalized messageId (what the dedupe cache uses) so the
+    // retry counter and downstream dedupe key agree on identity. Fall
+    // back to the raw BB `guid` only when normalization didn't supply one.
+    const retryKey = normalized.messageId ?? (typeof rec.guid === "string" ? rec.guid : "");
+
+    // Already-given-up GUIDs are skipped without another `processMessage`
+    // attempt. This is what lets catchup make forward progress through an
+    // earlier, still-retrying failure while not burning cycles re-running
+    // a permanently broken message every sweep.
+    const prevCount = retryKey ? (prevRetries[retryKey] ?? 0) : 0;
+    if (retryKey && prevCount >= maxFailureRetries) {
+      summary.skippedGivenUp++;
+      // Preserve the count so give-up stickiness survives this run.
+      nextRetries[retryKey] = prevCount;
+      continue;
+    }
+
     try {
       await procFn(normalized, target);
       summary.replayed++;
+      // Success clears any accumulated retries for this GUID. Since we
+      // build `nextRetries` from scratch rather than mutating
+      // `prevRetries`, simply NOT copying the entry is the clear. (We
+      // still need this branch so readers understand the lifecycle.)
     } catch (err) {
       summary.failed++;
-      if (ts > 0 && (earliestProcessFailureTs === null || ts < earliestProcessFailureTs)) {
-        earliestProcessFailureTs = ts;
+      const nextCount = prevCount + 1;
+      if (retryKey && nextCount >= maxFailureRetries) {
+        // Crossing the ceiling this run: log WARN once and record the
+        // give-up in the persisted map. Don't contribute to
+        // `earliestProcessFailureTs` — we're intentionally letting the
+        // cursor advance past this GUID on the next sweep.
+        summary.givenUp++;
+        nextRetries[retryKey] = nextCount;
+        error?.(
+          `[${accountId}] BlueBubbles catchup: giving up on guid=${retryKey} ` +
+            `after ${nextCount} consecutive failures; future sweeps will skip ` +
+            `this message. timestamp=${ts}: ${String(err)}`,
+        );
+      } else {
+        // Still retrying: count this failure and hold the cursor so the
+        // next sweep retries the same window. (retryKey may be empty in
+        // the unusual case where neither normalizer nor raw payload
+        // carried a GUID — in that case we hold the cursor but cannot
+        // increment a counter, matching pre-retry-cap behavior.)
+        if (retryKey) {
+          nextRetries[retryKey] = nextCount;
+        }
+        if (ts > 0 && (earliestProcessFailureTs === null || ts < earliestProcessFailureTs)) {
+          earliestProcessFailureTs = ts;
+        }
+        error?.(
+          `[${accountId}] BlueBubbles catchup: processMessage failed (retry ` +
+            `${nextCount}/${maxFailureRetries}): ${String(err)}`,
+        );
       }
-      error?.(`[${accountId}] BlueBubbles catchup: processMessage failed: ${String(err)}`);
     }
   }
 
@@ -381,10 +597,17 @@ async function runBlueBubblesCatchupInner(
   //   this sweep finished (avoiding stuck rescans of a message with
   //   `dateCreated > nowMs` from minor clock skew between BB host and
   //   gateway host).
-  // - On retryable failure (any `processMessage` throw): hold the cursor
-  //   just before the earliest failed timestamp so the next run retries
-  //   from there. The inbound-dedupe cache from #66230 keeps successfully
-  //   replayed messages from being re-processed.
+  // - On retryable failure (any still-retrying `processMessage` throw,
+  //   where the GUID has NOT crossed `maxFailureRetries`): hold the
+  //   cursor just before the earliest still-retrying failed timestamp so
+  //   the next run retries from there. The inbound-dedupe cache from
+  //   #66230 keeps successfully replayed messages from being re-processed.
+  // - On give-up (failures that crossed `maxFailureRetries`): the GUID
+  //   is recorded in the persisted retry map with `count >= max` and
+  //   skipped on sight in subsequent runs (without another processMessage
+  //   attempt). Give-up GUIDs intentionally do NOT hold the cursor, so
+  //   the cursor can advance past them naturally — this is what unwedges
+  //   catchup from a permanently malformed message (issue #66870).
   // - On truncation (fetched === perRunLimit): advance only to the latest
   //   fetched timestamp so the next run picks up from the page boundary.
   //   Otherwise the unfetched tail past the cap (which can be substantial
@@ -400,14 +623,18 @@ async function runBlueBubblesCatchupInner(
     nextCursorMs = Math.min(Math.max(latestFetchedTs, cursorBefore ?? windowStartMs), nowMs);
   }
   summary.cursorAfter = nextCursorMs;
-  await saveBlueBubblesCatchupCursor(accountId, nextCursorMs).catch((err) => {
+  // Cap the retry map before writing — defense in depth against a storm
+  // of unique failing GUIDs ballooning the cursor file.
+  const retriesToPersist = capFailureRetriesMap(nextRetries, MAX_FAILURE_RETRY_MAP_SIZE);
+  await saveBlueBubblesCatchupCursor(accountId, nextCursorMs, retriesToPersist).catch((err) => {
     error?.(`[${accountId}] BlueBubbles catchup: cursor save failed: ${String(err)}`);
   });
 
   log?.(
     `[${accountId}] BlueBubbles catchup: replayed=${summary.replayed} ` +
       `skipped_fromMe=${summary.skippedFromMe} skipped_preCursor=${summary.skippedPreCursor} ` +
-      `failed=${summary.failed} fetched=${summary.fetchedCount} ` +
+      `skipped_givenUp=${summary.skippedGivenUp} failed=${summary.failed} ` +
+      `given_up=${summary.givenUp} fetched=${summary.fetchedCount} ` +
       `window_ms=${nowMs - windowStartMs}`,
   );
 
diff --git a/extensions/bluebubbles/src/config-schema.ts b/extensions/bluebubbles/src/config-schema.ts
index 22282989475..a4b7fb5e7b3 100644
--- a/extensions/bluebubbles/src/config-schema.ts
+++ b/extensions/bluebubbles/src/config-schema.ts
@@ -50,6 +50,14 @@ const bluebubblesCatchupSchema = z
     perRunLimit: z.number().int().positive().optional(),
     /** First-run lookback used when no cursor has been persisted yet. Clamped to [1, 720]. */
     firstRunLookbackMinutes: z.number().int().positive().optional(),
+    /**
+     * Consecutive-failure ceiling per message GUID. After this many failed
+     * processMessage attempts against the same GUID, catchup logs a WARN
+     * and skips the message on subsequent sweeps (letting the cursor
+     * advance past a permanently malformed payload). Defaults to 10.
+     * Clamped to [1, 1000].
+     */
+    maxFailureRetries: z.number().int().positive().optional(),
   })
   .strict()
   .optional();
diff --git a/extensions/bluebubbles/src/inbound-dedupe.ts b/extensions/bluebubbles/src/inbound-dedupe.ts
index 8327b899710..deffa49685f 100644
--- a/extensions/bluebubbles/src/inbound-dedupe.ts
+++ b/extensions/bluebubbles/src/inbound-dedupe.ts
@@ -1,4 +1,5 @@
 import { createHash } from "node:crypto";
+import fs from "node:fs";
 import path from "node:path";
 import { type ClaimableDedupe, createClaimableDedupe } from "openclaw/plugin-sdk/persistent-dedupe";
 import { resolveStateDir } from "openclaw/plugin-sdk/state-paths";
@@ -33,6 +34,11 @@ function resolveStateDirFromEnv(env: NodeJS.ProcessEnv = process.env): string {
   return resolveStateDir(env);
 }
 
+function resolveLegacyNamespaceFilePath(namespace: string): string {
+  const safe = namespace.replace(/[^a-zA-Z0-9_-]/g, "_") || "global";
+  return path.join(resolveStateDirFromEnv(), "bluebubbles", "inbound-dedupe", `${safe}.json`);
+}
+
 function resolveNamespaceFilePath(namespace: string): string {
   // Keep a readable prefix for operator debugging, but suffix with a short
   // hash of the raw namespace so account IDs that only differ by
@@ -40,12 +46,42 @@ function resolveNamespaceFilePath(namespace: string): string {
   // onto the same file.
   const safePrefix = namespace.replace(/[^a-zA-Z0-9_-]/g, "_") || "ns";
   const hash = createHash("sha256").update(namespace, "utf8").digest("hex").slice(0, 12);
-  return path.join(
-    resolveStateDirFromEnv(),
-    "bluebubbles",
-    "inbound-dedupe",
-    `${safePrefix}__${hash}.json`,
-  );
+  const dir = path.join(resolveStateDirFromEnv(), "bluebubbles", "inbound-dedupe");
+  const newPath = path.join(dir, `${safePrefix}__${hash}.json`);
+
+  // One-time migration: earlier beta shipped `${safe}.json` (no hash).
+  // Rename so the upgrade preserves existing dedupe entries instead of
+  // starting from an empty file and replaying already-handled messages.
+  migrateLegacyDedupeFile(namespace, newPath);
+
+  return newPath;
+}
+
+const migratedNamespaces = new Set<string>();
+
+function migrateLegacyDedupeFile(namespace: string, newPath: string): void {
+  if (migratedNamespaces.has(namespace)) {
+    return;
+  }
+  migratedNamespaces.add(namespace);
+  try {
+    const legacyPath = resolveLegacyNamespaceFilePath(namespace);
+    if (legacyPath === newPath) {
+      return;
+    }
+    if (!fs.existsSync(legacyPath)) {
+      return;
+    }
+    if (!fs.existsSync(newPath)) {
+      fs.renameSync(legacyPath, newPath);
+    } else {
+      // Both exist: new file is authoritative; remove the stale legacy.
+      fs.unlinkSync(legacyPath);
+    }
+  } catch {
+    // Best-effort migration; a missed rename is strictly less harmful
+    // than crashing the module load path.
+  }
 }
 
 function buildPersistentImpl(): ClaimableDedupe {
@@ -162,6 +198,18 @@ export async function claimBlueBubblesInboundMessage(params: {
   };
 }
 
+/**
+ * Ensure the legacy→hashed dedupe file migration runs and the on-disk
+ * store is warmed into memory for the given account. Call before any
+ * catchup replay so already-handled GUIDs are recognized even when the
+ * file-naming convention changed between versions.
+ */
+export async function warmupBlueBubblesInboundDedupe(accountId: string): Promise<void> {
+  // Trigger the migration side-effect inside resolveNamespaceFilePath.
+  resolveNamespaceFilePath(accountId);
+  await impl.warmup(accountId);
+}
+
 /**
  * Reset inbound dedupe state between tests. Installs an in-memory-only
  * implementation so tests do not hit disk, avoiding file-lock timing issues
diff --git a/src/plugin-sdk/persistent-dedupe.ts b/src/plugin-sdk/persistent-dedupe.ts
index 79dd33e2779..651a5b9193f 100644
--- a/src/plugin-sdk/persistent-dedupe.ts
+++ b/src/plugin-sdk/persistent-dedupe.ts
@@ -154,6 +154,35 @@ export function createPersistentDedupe(options: PersistentDedupeOptions): Persis
   const lockOptions = mergeLockOptions(options.lockOptions);
   const memory = createDedupeCache({ ttlMs, maxSize: memoryMaxSize });
   const inflight = new Map<string, Promise<boolean>>();
+  // In-process write queue per file path. `withFileLock` is re-entrant
+  // within the same process (a second caller for the same path gets
+  // immediate access instead of waiting), so two concurrent
+  // checkAndRecordInner calls for different keys but the same file can
+  // race: both read the same stale data, and the last writer's
+  // writeJsonFileAtomically silently overwrites the first writer's
+  // additions. This queue serializes all read-modify-write cycles
+  // targeting the same file within this process, preventing the lost
+  // update while still allowing cross-process file-lock contention to
+  // be handled by the file lock itself.
+  const fileWriteQueues = new Map<string, Promise<unknown>>();
+
+  function enqueueFileWrite<T>(filePath: string, fn: () => Promise<T>): Promise<T> {
+    const prev = fileWriteQueues.get(filePath) ?? Promise.resolve();
+    const next = prev.then(fn, fn);
+    fileWriteQueues.set(filePath, next);
+    // Cleanup: remove the queue entry once this link settles, but only if
+    // no newer work was chained after us. The `.catch(() => {})` prevents
+    // an unhandled rejection when `next` rejects — callers still observe
+    // the rejection through the returned `next` promise directly.
+    next
+      .finally(() => {
+        if (fileWriteQueues.get(filePath) === next) {
+          fileWriteQueues.delete(filePath);
+        }
+      })
+      .catch(() => {});
+    return next;
+  }
 
   async function checkAndRecordInner(
     key: string,
@@ -168,19 +197,21 @@ export function createPersistentDedupe(options: PersistentDedupeOptions): Persis
 
     const path = options.resolveFilePath(namespace);
     try {
-      const duplicate = await withFileLock(path, lockOptions, async () => {
-        const { value } = await readJsonFileWithFallback<PersistentDedupeData>(path, {});
-        const data = sanitizeData(value);
-        const seenAt = data[key];
-        const isRecent = seenAt != null && (ttlMs <= 0 || now - seenAt < ttlMs);
-        if (isRecent) {
-          return true;
-        }
-        data[key] = now;
-        pruneData(data, now, ttlMs, fileMaxEntries);
-        await writeJsonFileAtomically(path, data);
-        return false;
-      });
+      const duplicate = await enqueueFileWrite(path, () =>
+        withFileLock(path, lockOptions, async () => {
+          const { value } = await readJsonFileWithFallback<PersistentDedupeData>(path, {});
+          const data = sanitizeData(value);
+          const seenAt = data[key];
+          const isRecent = seenAt != null && (ttlMs <= 0 || now - seenAt < ttlMs);
+          if (isRecent) {
+            return true;
+          }
+          data[key] = now;
+          pruneData(data, now, ttlMs, fileMaxEntries);
+          await writeJsonFileAtomically(path, data);
+          return false;
+        }),
+      );
       return !duplicate;
     } catch (error) {
       onDiskError?.(error);