diff --git a/src/cron/delivery-plan.ts b/src/cron/delivery-plan.ts
new file mode 100644
index 00000000000..a04d4c64629
--- /dev/null
+++ b/src/cron/delivery-plan.ts
@@ -0,0 +1,233 @@
+import type { CronFailureDestinationConfig } from "../config/types.cron.js";
+import type { CronDelivery, CronDeliveryMode, CronJob, CronMessageChannel } from "./types.js";
+
+export type CronDeliveryPlan = {
+  mode: CronDeliveryMode;
+  channel?: CronMessageChannel;
+  to?: string;
+  threadId?: string | number;
+  /** Explicit channel account id from the delivery config, if set. */
+  accountId?: string;
+  source: "delivery";
+  requested: boolean;
+};
+
+function normalizeChannel(value: unknown): CronMessageChannel | undefined {
+  if (typeof value !== "string") {
+    return undefined;
+  }
+  const trimmed = value.trim().toLowerCase();
+  if (!trimmed) {
+    return undefined;
+  }
+  return trimmed as CronMessageChannel;
+}
+
+function normalizeTo(value: unknown): string | undefined {
+  if (typeof value !== "string") {
+    return undefined;
+  }
+  const trimmed = value.trim();
+  return trimmed ? trimmed : undefined;
+}
+
+function normalizeAccountId(value: unknown): string | undefined {
+  if (typeof value !== "string") {
+    return undefined;
+  }
+  const trimmed = value.trim();
+  return trimmed ? trimmed : undefined;
+}
+
+function normalizeThreadId(value: unknown): string | number | undefined {
+  if (typeof value === "number" && Number.isFinite(value)) {
+    return value;
+  }
+  if (typeof value !== "string") {
+    return undefined;
+  }
+  const trimmed = value.trim();
+  return trimmed ? trimmed : undefined;
+}
+
+export function resolveCronDeliveryPlan(job: CronJob): CronDeliveryPlan {
+  const delivery = job.delivery;
+  const hasDelivery = delivery && typeof delivery === "object";
+  const rawMode = hasDelivery ? (delivery as { mode?: unknown }).mode : undefined;
+  const normalizedMode = typeof rawMode === "string" ? rawMode.trim().toLowerCase() : rawMode;
+  const mode =
+    normalizedMode === "announce"
+      ? "announce"
+      : normalizedMode === "webhook"
+        ? "webhook"
+        : normalizedMode === "none"
+          ? "none"
+          : normalizedMode === "deliver"
+            ? "announce"
+            : undefined;
+
+  const deliveryChannel = normalizeChannel(
+    (delivery as { channel?: unknown } | undefined)?.channel,
+  );
+  const deliveryTo = normalizeTo((delivery as { to?: unknown } | undefined)?.to);
+  const deliveryThreadId = normalizeThreadId(
+    (delivery as { threadId?: unknown } | undefined)?.threadId,
+  );
+  const channel = deliveryChannel ?? "last";
+  const to = deliveryTo;
+  const deliveryAccountId = normalizeAccountId(
+    (delivery as { accountId?: unknown } | undefined)?.accountId,
+  );
+  if (hasDelivery) {
+    const resolvedMode = mode ?? "announce";
+    return {
+      mode: resolvedMode,
+      channel: resolvedMode === "announce" ? channel : undefined,
+      to,
+      threadId: resolvedMode === "announce" ? deliveryThreadId : undefined,
+      accountId: deliveryAccountId,
+      source: "delivery",
+      requested: resolvedMode === "announce",
+    };
+  }
+
+  const isIsolatedAgentTurn =
+    job.payload.kind === "agentTurn" &&
+    (job.sessionTarget === "isolated" ||
+      job.sessionTarget === "current" ||
+      job.sessionTarget.startsWith("session:"));
+  const resolvedMode = isIsolatedAgentTurn ? "announce" : "none";
+
+  return {
+    mode: resolvedMode,
+    channel: resolvedMode === "announce" ? "last" : undefined,
+    to: undefined,
+    threadId: undefined,
+    source: "delivery",
+    requested: resolvedMode === "announce",
+  };
+}
+
+export type CronFailureDeliveryPlan = {
+  mode: "announce" | "webhook";
+  channel?: CronMessageChannel;
+  to?: string;
+  accountId?: string;
+};
+
+export type CronFailureDestinationInput = {
+  channel?: CronMessageChannel;
+  to?: string;
+  accountId?: string;
+  mode?: "announce" | "webhook";
+};
+
+function normalizeFailureMode(value: unknown): "announce" | "webhook" | undefined {
+  if (typeof value !== "string") {
+    return undefined;
+  }
+  const trimmed = value.trim().toLowerCase();
+  if (trimmed === "announce" || trimmed === "webhook") {
+    return trimmed;
+  }
+  return undefined;
+}
+
+export function resolveFailureDestination(
+  job: CronJob,
+  globalConfig?: CronFailureDestinationConfig,
+): CronFailureDeliveryPlan | null {
+  const delivery = job.delivery;
+  const jobFailureDest = delivery?.failureDestination as CronFailureDestinationInput | undefined;
+  const hasJobFailureDest = jobFailureDest && typeof jobFailureDest === "object";
+
+  let channel: CronMessageChannel | undefined;
+  let to: string | undefined;
+  let accountId: string | undefined;
+  let mode: "announce" | "webhook" | undefined;
+
+  if (globalConfig) {
+    channel = normalizeChannel(globalConfig.channel);
+    to = normalizeTo(globalConfig.to);
+    accountId = normalizeAccountId(globalConfig.accountId);
+    mode = normalizeFailureMode(globalConfig.mode);
+  }
+
+  if (hasJobFailureDest) {
+    const jobChannel = normalizeChannel(jobFailureDest.channel);
+    const jobTo = normalizeTo(jobFailureDest.to);
+    const jobAccountId = normalizeAccountId(jobFailureDest.accountId);
+    const jobMode = normalizeFailureMode(jobFailureDest.mode);
+    const hasJobChannelField = "channel" in jobFailureDest;
+    const hasJobToField = "to" in jobFailureDest;
+    const hasJobAccountIdField = "accountId" in jobFailureDest;
+
+    const jobToExplicitValue = hasJobToField && jobTo !== undefined;
+
+    if (hasJobChannelField) {
+      channel = jobChannel;
+    }
+    if (hasJobToField) {
+      to = jobTo;
+    }
+    if (hasJobAccountIdField) {
+      accountId = jobAccountId;
+    }
+    if (jobMode !== undefined) {
+      const globalMode = globalConfig?.mode ?? "announce";
+      if (!jobToExplicitValue && globalMode !== jobMode) {
+        to = undefined;
+      }
+      mode = jobMode;
+    }
+  }
+
+  if (!channel && !to && !accountId && !mode) {
+    return null;
+  }
+
+  const resolvedMode = mode ?? "announce";
+  if (resolvedMode === "webhook" && !to) {
+    return null;
+  }
+
+  const result: CronFailureDeliveryPlan = {
+    mode: resolvedMode,
+    channel: resolvedMode === "announce" ? (channel ?? "last") : undefined,
+    to,
+    accountId,
+  };
+
+  if (delivery && isSameDeliveryTarget(delivery, result)) {
+    return null;
+  }
+
+  return result;
+}
+
+function isSameDeliveryTarget(
+  delivery: CronDelivery,
+  failurePlan: CronFailureDeliveryPlan,
+): boolean {
+  const primaryMode = delivery.mode ?? "announce";
+  if (primaryMode === "none") {
+    return false;
+  }
+
+  const primaryChannel = delivery.channel;
+  const primaryTo = delivery.to;
+  const primaryAccountId = delivery.accountId;
+
+  if (failurePlan.mode === "webhook") {
+    return primaryMode === "webhook" && primaryTo === failurePlan.to;
+  }
+
+  const primaryChannelNormalized = primaryChannel ?? "last";
+  const failureChannelNormalized = failurePlan.channel ?? "last";
+
+  return (
+    failureChannelNormalized === primaryChannelNormalized &&
+    failurePlan.to === primaryTo &&
+    failurePlan.accountId === primaryAccountId
+  );
+}
diff --git a/src/cron/delivery.test.ts b/src/cron/delivery.test.ts
index 2a2e2aa29ab..f30ddb22d4a 100644
--- a/src/cron/delivery.test.ts
+++ b/src/cron/delivery.test.ts
@@ -1,5 +1,5 @@
 import { describe, expect, it } from "vitest";
-import { resolveCronDeliveryPlan, resolveFailureDestination } from "./delivery.js";
+import { resolveCronDeliveryPlan, resolveFailureDestination } from "./delivery-plan.js";
 import type { CronJob } from "./types.js";
 
 function makeJob(overrides: Partial<CronJob>): CronJob {
diff --git a/src/cron/delivery.ts b/src/cron/delivery.ts
index 2f2e29fedac..74cb24e6aec 100644
--- a/src/cron/delivery.ts
+++ b/src/cron/delivery.ts
@@ -1,256 +1,29 @@
 import type { CliDeps } from "../cli/deps.js";
 import { createOutboundSendDeps } from "../cli/outbound-send-deps.js";
-import type { CronFailureDestinationConfig } from "../config/types.cron.js";
 import type { OpenClawConfig } from "../config/types.js";
 import { formatErrorMessage } from "../infra/errors.js";
 import { deliverOutboundPayloads } from "../infra/outbound/deliver.js";
 import { resolveAgentOutboundIdentity } from "../infra/outbound/identity.js";
 import { buildOutboundSessionContext } from "../infra/outbound/session-context.js";
 import { getChildLogger } from "../logging.js";
+import {
+  resolveFailureDestination,
+  type CronFailureDeliveryPlan,
+  type CronFailureDestinationInput,
+  type CronDeliveryPlan,
+  resolveCronDeliveryPlan,
+} from "./delivery-plan.js";
 import { resolveDeliveryTarget } from "./isolated-agent/delivery-target.js";
-import type { CronDelivery, CronDeliveryMode, CronJob, CronMessageChannel } from "./types.js";
+import type { CronMessageChannel } from "./types.js";
 
-export type CronDeliveryPlan = {
-  mode: CronDeliveryMode;
-  channel?: CronMessageChannel;
-  to?: string;
-  threadId?: string | number;
-  /** Explicit channel account id from the delivery config, if set. */
-  accountId?: string;
-  source: "delivery";
-  requested: boolean;
+export {
+  resolveCronDeliveryPlan,
+  resolveFailureDestination,
+  type CronDeliveryPlan,
+  type CronFailureDeliveryPlan,
+  type CronFailureDestinationInput,
 };
 
-function normalizeChannel(value: unknown): CronMessageChannel | undefined {
-  if (typeof value !== "string") {
-    return undefined;
-  }
-  const trimmed = value.trim().toLowerCase();
-  if (!trimmed) {
-    return undefined;
-  }
-  return trimmed as CronMessageChannel;
-}
-
-function normalizeTo(value: unknown): string | undefined {
-  if (typeof value !== "string") {
-    return undefined;
-  }
-  const trimmed = value.trim();
-  return trimmed ? trimmed : undefined;
-}
-
-function normalizeAccountId(value: unknown): string | undefined {
-  if (typeof value !== "string") {
-    return undefined;
-  }
-  const trimmed = value.trim();
-  return trimmed ? trimmed : undefined;
-}
-
-function normalizeThreadId(value: unknown): string | number | undefined {
-  if (typeof value === "number" && Number.isFinite(value)) {
-    return value;
-  }
-  if (typeof value !== "string") {
-    return undefined;
-  }
-  const trimmed = value.trim();
-  return trimmed ? trimmed : undefined;
-}
-
-export function resolveCronDeliveryPlan(job: CronJob): CronDeliveryPlan {
-  const delivery = job.delivery;
-  const hasDelivery = delivery && typeof delivery === "object";
-  const rawMode = hasDelivery ? (delivery as { mode?: unknown }).mode : undefined;
-  const normalizedMode = typeof rawMode === "string" ? rawMode.trim().toLowerCase() : rawMode;
-  const mode =
-    normalizedMode === "announce"
-      ? "announce"
-      : normalizedMode === "webhook"
-        ? "webhook"
-        : normalizedMode === "none"
-          ? "none"
-          : normalizedMode === "deliver"
-            ? "announce"
-            : undefined;
-
-  const deliveryChannel = normalizeChannel(
-    (delivery as { channel?: unknown } | undefined)?.channel,
-  );
-  const deliveryTo = normalizeTo((delivery as { to?: unknown } | undefined)?.to);
-  const deliveryThreadId = normalizeThreadId(
-    (delivery as { threadId?: unknown } | undefined)?.threadId,
-  );
-  const channel = deliveryChannel ?? "last";
-  const to = deliveryTo;
-  const deliveryAccountId = normalizeAccountId(
-    (delivery as { accountId?: unknown } | undefined)?.accountId,
-  );
-  if (hasDelivery) {
-    const resolvedMode = mode ?? "announce";
-    return {
-      mode: resolvedMode,
-      channel: resolvedMode === "announce" ? channel : undefined,
-      to,
-      threadId: resolvedMode === "announce" ? deliveryThreadId : undefined,
-      accountId: deliveryAccountId,
-      source: "delivery",
-      requested: resolvedMode === "announce",
-    };
-  }
-
-  const isIsolatedAgentTurn =
-    job.payload.kind === "agentTurn" &&
-    (job.sessionTarget === "isolated" ||
-      job.sessionTarget === "current" ||
-      job.sessionTarget.startsWith("session:"));
-  const resolvedMode = isIsolatedAgentTurn ? "announce" : "none";
-
-  return {
-    mode: resolvedMode,
-    channel: resolvedMode === "announce" ? "last" : undefined,
-    to: undefined,
-    threadId: undefined,
-    source: "delivery",
-    requested: resolvedMode === "announce",
-  };
-}
-
-export type CronFailureDeliveryPlan = {
-  mode: "announce" | "webhook";
-  channel?: CronMessageChannel;
-  to?: string;
-  accountId?: string;
-};
-
-export type CronFailureDestinationInput = {
-  channel?: CronMessageChannel;
-  to?: string;
-  accountId?: string;
-  mode?: "announce" | "webhook";
-};
-
-function normalizeFailureMode(value: unknown): "announce" | "webhook" | undefined {
-  if (typeof value !== "string") {
-    return undefined;
-  }
-  const trimmed = value.trim().toLowerCase();
-  if (trimmed === "announce" || trimmed === "webhook") {
-    return trimmed;
-  }
-  return undefined;
-}
-
-export function resolveFailureDestination(
-  job: CronJob,
-  globalConfig?: CronFailureDestinationConfig,
-): CronFailureDeliveryPlan | null {
-  const delivery = job.delivery;
-  const jobFailureDest = delivery?.failureDestination as CronFailureDestinationInput | undefined;
-  const hasJobFailureDest = jobFailureDest && typeof jobFailureDest === "object";
-
-  let channel: CronMessageChannel | undefined;
-  let to: string | undefined;
-  let accountId: string | undefined;
-  let mode: "announce" | "webhook" | undefined;
-
-  // Start with global config as base
-  if (globalConfig) {
-    channel = normalizeChannel(globalConfig.channel);
-    to = normalizeTo(globalConfig.to);
-    accountId = normalizeAccountId(globalConfig.accountId);
-    mode = normalizeFailureMode(globalConfig.mode);
-  }
-
-  // Override with job-level values if present
-  if (hasJobFailureDest) {
-    const jobChannel = normalizeChannel(jobFailureDest.channel);
-    const jobTo = normalizeTo(jobFailureDest.to);
-    const jobAccountId = normalizeAccountId(jobFailureDest.accountId);
-    const jobMode = normalizeFailureMode(jobFailureDest.mode);
-    const hasJobChannelField = "channel" in jobFailureDest;
-    const hasJobToField = "to" in jobFailureDest;
-    const hasJobAccountIdField = "accountId" in jobFailureDest;
-
-    // Track if 'to' was explicitly set at job level
-    const jobToExplicitValue = hasJobToField && jobTo !== undefined;
-
-    // Respect explicit clears from partial patches.
-    if (hasJobChannelField) {
-      channel = jobChannel;
-    }
-    if (hasJobToField) {
-      to = jobTo;
-    }
-    if (hasJobAccountIdField) {
-      accountId = jobAccountId;
-    }
-    if (jobMode !== undefined) {
-      // Mode was explicitly overridden - clear inherited 'to' since URL semantics differ
-      // between announce (channel recipient) and webhook (HTTP endpoint)
-      // But preserve explicit 'to' that was set at job level
-      // Treat undefined global mode as "announce" for comparison
-      const globalMode = globalConfig?.mode ?? "announce";
-      if (!jobToExplicitValue && globalMode !== jobMode) {
-        to = undefined;
-      }
-      mode = jobMode;
-    }
-  }
-
-  if (!channel && !to && !accountId && !mode) {
-    return null;
-  }
-
-  const resolvedMode = mode ?? "announce";
-
-  // Webhook mode requires a URL
-  if (resolvedMode === "webhook" && !to) {
-    return null;
-  }
-
-  const result: CronFailureDeliveryPlan = {
-    mode: resolvedMode,
-    channel: resolvedMode === "announce" ? (channel ?? "last") : undefined,
-    to,
-    accountId,
-  };
-
-  if (delivery && isSameDeliveryTarget(delivery, result)) {
-    return null;
-  }
-
-  return result;
-}
-
-function isSameDeliveryTarget(
-  delivery: CronDelivery,
-  failurePlan: CronFailureDeliveryPlan,
-): boolean {
-  const primaryMode = delivery.mode ?? "announce";
-  if (primaryMode === "none") {
-    return false;
-  }
-
-  const primaryChannel = delivery.channel;
-  const primaryTo = delivery.to;
-  const primaryAccountId = delivery.accountId;
-
-  if (failurePlan.mode === "webhook") {
-    return primaryMode === "webhook" && primaryTo === failurePlan.to;
-  }
-
-  const primaryChannelNormalized = primaryChannel ?? "last";
-  const failureChannelNormalized = failurePlan.channel ?? "last";
-
-  return (
-    failureChannelNormalized === primaryChannelNormalized &&
-    failurePlan.to === primaryTo &&
-    failurePlan.accountId === primaryAccountId
-  );
-}
-
 const FAILURE_NOTIFICATION_TIMEOUT_MS = 30_000;
 const cronDeliveryLogger = getChildLogger({ subsystem: "cron-delivery" });
 
diff --git a/src/cron/isolated-agent/run.test-harness.ts b/src/cron/isolated-agent/run.test-harness.ts
index df7543c8ded..4daa91fee7e 100644
--- a/src/cron/isolated-agent/run.test-harness.ts
+++ b/src/cron/isolated-agent/run.test-harness.ts
@@ -245,7 +245,7 @@ vi.mock("../../security/external-content.js", async (importOriginal) => {
   };
 });
 
-vi.mock("../delivery.js", () => ({
+vi.mock("../delivery-plan.js", () => ({
   resolveCronDeliveryPlan: resolveCronDeliveryPlanMock,
 }));
 
diff --git a/src/cron/isolated-agent/run.ts b/src/cron/isolated-agent/run.ts
index b3eb1c2cfde..b3eb4b61965 100644
--- a/src/cron/isolated-agent/run.ts
+++ b/src/cron/isolated-agent/run.ts
@@ -43,7 +43,7 @@ import {
   isExternalHookSession,
   resolveHookExternalContentSource,
 } from "../../security/external-content.js";
-import { resolveCronDeliveryPlan } from "../delivery.js";
+import { resolveCronDeliveryPlan } from "../delivery-plan.js";
 import type { CronJob, CronRunOutcome, CronRunTelemetry } from "../types.js";
 import {
   dispatchCronDelivery,
diff --git a/src/cron/service/timer.ts b/src/cron/service/timer.ts
index 36442c06b53..edd9f93c2b6 100644
--- a/src/cron/service/timer.ts
+++ b/src/cron/service/timer.ts
@@ -7,7 +7,7 @@ import {
   createRunningTaskRun,
   failTaskRunByRunId,
 } from "../../tasks/task-executor.js";
-import { resolveCronDeliveryPlan } from "../delivery.js";
+import { resolveCronDeliveryPlan } from "../delivery-plan.js";
 import { sweepCronRunSessions } from "../session-reaper.js";
 import type {
   CronDeliveryStatus,