diff --git a/CHANGELOG.md b/CHANGELOG.md
index c2036917a64..1740725504d 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -44,6 +44,7 @@ Docs: https://docs.openclaw.ai
 - Gateway/startup: fix spurious SIGUSR1 restart loop on Linux/systemd when plugin auto-enable is the only startup config write; the config hash guard was not captured for that write path, causing chokidar to treat each boot write as an external change and trigger a reload → restart cycle that corrupts manifest.db after repeated cycles. Fixes #67436. (#67557) thanks @openperf
 - OpenAI Codex/CLI: keep resumed `codex exec resume` runs on the safe non-interactive path without reintroducing the removed dangerous bypass flag by passing the supported `--skip-git-repo-check` resume arg that real Codex CLI requires outside trusted git directories. (#67666) Thanks @plgonzalezrx8.
 - Codex/app-server: parse Desktop-originated app-server user agents such as `Codex Desktop/0.118.0`, keeping the version gate working when the Codex CLI inherits a multi-word originator. (#64666) Thanks @cyrusaf.
+- Cron/announce delivery: keep isolated announce `NO_REPLY` stripping case-insensitive across direct and text delivery, preserve structured media-only sends when a caption strips silent, and derive main-session awareness from the cleaned payloads so silent captions no longer leak stale `NO_REPLY` text. (#65016) Thanks @BKF-Gitty.
 
 ## 2026.4.15-beta.1
 
diff --git a/src/agents/subagent-announce.ts b/src/agents/subagent-announce.ts
index db308f55657..cce280e6480 100644
--- a/src/agents/subagent-announce.ts
+++ b/src/agents/subagent-announce.ts
@@ -1,4 +1,10 @@
-import { isSilentReplyText, SILENT_REPLY_TOKEN } from "../auto-reply/tokens.js";
+import {
+  isSilentReplyText,
+  SILENT_REPLY_TOKEN,
+  startsWithSilentToken,
+  stripLeadingSilentToken,
+  stripSilentToken,
+} from "../auto-reply/tokens.js";
 import { defaultRuntime } from "../runtime.js";
 import { isCronSessionKey } from "../sessions/session-key-utils.js";
 import { normalizeOptionalString } from "../shared/string-coerce.js";
@@ -127,6 +133,27 @@ function isWakeContinuationRun(runId: string): boolean {
   return stripWakeRunSuffixes(trimmed) !== trimmed;
 }
 
+function stripAndClassifyReply(text: string): string | null {
+  let result = text;
+  let didStrip = false;
+  const hasLeadingSilentToken = startsWithSilentToken(result, SILENT_REPLY_TOKEN);
+  if (hasLeadingSilentToken) {
+    result = stripLeadingSilentToken(result, SILENT_REPLY_TOKEN);
+    didStrip = true;
+  }
+  if (hasLeadingSilentToken || result.toLowerCase().includes(SILENT_REPLY_TOKEN.toLowerCase())) {
+    result = stripSilentToken(result, SILENT_REPLY_TOKEN);
+    didStrip = true;
+  }
+  if (
+    didStrip &&
+    (!result.trim() || isSilentReplyText(result, SILENT_REPLY_TOKEN) || isAnnounceSkip(result))
+  ) {
+    return null;
+  }
+  return result;
+}
+
 async function wakeSubagentRunAfterDescendants(params: {
   runId: string;
   childSessionKey: string;
@@ -385,10 +412,29 @@ export async function runSubagentAnnounceFlow(params: {
 
       if (isAnnounceSkip(reply) || isSilentReplyText(reply, SILENT_REPLY_TOKEN)) {
         if (fallbackReply && !fallbackIsSilent) {
-          reply = fallbackReply;
+          const cleaned = stripAndClassifyReply(fallbackReply);
+          if (cleaned === null) {
+            return true;
+          }
+          reply = cleaned;
         } else {
           return true;
         }
+      } else if (reply) {
+        const cleaned = stripAndClassifyReply(reply);
+        if (cleaned === null) {
+          if (fallbackReply && !fallbackIsSilent) {
+            const cleanedFallback = stripAndClassifyReply(fallbackReply);
+            if (cleanedFallback === null) {
+              return true;
+            }
+            reply = cleanedFallback;
+          } else {
+            return true;
+          }
+        } else {
+          reply = cleaned;
+        }
       }
     }
 
diff --git a/src/auto-reply/reply/normalize-reply.ts b/src/auto-reply/reply/normalize-reply.ts
index c6a1065d1a1..e8883ff6bab 100644
--- a/src/auto-reply/reply/normalize-reply.ts
+++ b/src/auto-reply/reply/normalize-reply.ts
@@ -69,7 +69,7 @@ export function normalizeReplyPayload(
     if (hasLeadingSilentToken) {
       text = stripLeadingSilentToken(text, silentToken);
     }
-    if (hasLeadingSilentToken || text.includes(silentToken)) {
+    if (hasLeadingSilentToken || text.toLowerCase().includes(silentToken.toLowerCase())) {
       text = stripSilentToken(text, silentToken);
       if (!hasContent(text)) {
         opts.onSkip?.("silent");
diff --git a/src/auto-reply/tokens.ts b/src/auto-reply/tokens.ts
index ea6c47dc9ff..3385fde95d8 100644
--- a/src/auto-reply/tokens.ts
+++ b/src/auto-reply/tokens.ts
@@ -24,7 +24,7 @@ function getSilentTrailingRegex(token: string): RegExp {
     return cached;
   }
   const escaped = escapeRegExp(token);
-  const regex = new RegExp(`(?:^|\\s+|\\*+)${escaped}\\s*$`);
+  const regex = new RegExp(`(?:^|\\s+|\\*+)${escaped}\\s*$`, "i");
   silentTrailingRegexByToken.set(token, regex);
   return regex;
 }
diff --git a/src/cron/isolated-agent/delivery-dispatch.double-announce.test.ts b/src/cron/isolated-agent/delivery-dispatch.double-announce.test.ts
index 413eacb957c..52dc888b592 100644
--- a/src/cron/isolated-agent/delivery-dispatch.double-announce.test.ts
+++ b/src/cron/isolated-agent/delivery-dispatch.double-announce.test.ts
@@ -122,7 +122,7 @@ function makeBaseParams(overrides: {
   runSessionId?: string;
   sessionTarget?: string;
   deliveryBestEffort?: boolean;
-}) {
+}): Parameters<typeof dispatchCronDelivery>[0] {
   const resolvedDelivery = makeResolvedDelivery();
   return {
     cfg: {} as never,
@@ -327,6 +327,32 @@ describe("dispatchCronDelivery — double-announce guard", () => {
     });
   });
 
+  it("skips awareness text when direct delivery strips a silent caption", async () => {
+    vi.mocked(countActiveDescendantRuns).mockReturnValue(0);
+    vi.mocked(isLikelyInterimCronMessage).mockReturnValue(false);
+
+    const params = makeBaseParams({ synthesizedText: undefined });
+    params.deliveryPayloadHasStructuredContent = true;
+    params.deliveryPayloads = [
+      { mediaUrl: "https://example.com/image.png", text: "All done\n\nNO_REPLY" },
+    ];
+    params.outputText = "All done\n\nNO_REPLY";
+    params.summary = "All done\n\nNO_REPLY";
+
+    const state = await dispatchCronDelivery(params);
+
+    expect(state.result).toBeUndefined();
+    expect(state.delivered).toBe(true);
+    expect(state.deliveryAttempted).toBe(true);
+    expect(deliverOutboundPayloads).toHaveBeenCalledTimes(1);
+    expect(deliverOutboundPayloads).toHaveBeenCalledWith(
+      expect.objectContaining({
+        payloads: [{ mediaUrl: "https://example.com/image.png", text: undefined }],
+      }),
+    );
+    expect(enqueueSystemEvent).not.toHaveBeenCalled();
+  });
+
   it("keeps the cron run successful when awareness queueing throws after delivery", async () => {
     vi.mocked(countActiveDescendantRuns).mockReturnValue(0);
     vi.mocked(isLikelyInterimCronMessage).mockReturnValue(false);
@@ -986,4 +1012,73 @@ describe("dispatchCronDelivery — double-announce guard", () => {
       expect.objectContaining({ status: "ok", delivered: false, deliveryAttempted: true }),
     );
   });
+
+  it("delivers substantive text that mentions NO_REPLY in non-trailing content (text delivery)", async () => {
+    vi.mocked(countActiveDescendantRuns).mockReturnValue(0);
+    vi.mocked(isLikelyInterimCronMessage).mockReturnValue(false);
+
+    const params = makeBaseParams({
+      synthesizedText:
+        "The NO_REPLY sentinel tells the agent to skip delivery when nothing changes.",
+    });
+    const state = await dispatchCronDelivery(params);
+
+    expect(state.deliveryAttempted).toBe(true);
+    expect(state.delivered).toBe(true);
+    expect(deliverOutboundPayloads).toHaveBeenCalledTimes(1);
+  });
+
+  it("delivers substantive text that mentions NO_REPLY in non-trailing content (direct delivery)", async () => {
+    vi.mocked(countActiveDescendantRuns).mockReturnValue(0);
+    vi.mocked(isLikelyInterimCronMessage).mockReturnValue(false);
+
+    const params = makeBaseParams({
+      synthesizedText:
+        "Reminder: reply NO_REPLY when there is nothing to announce, otherwise send a summary.",
+    });
+    (params as Record<string, unknown>).deliveryPayloadHasStructuredContent = true;
+    const state = await dispatchCronDelivery(params);
+
+    expect(state.deliveryAttempted).toBe(true);
+    expect(state.delivered).toBe(true);
+    expect(deliverOutboundPayloads).toHaveBeenCalledTimes(1);
+  });
+
+  it("delivers non-trailing NO_REPLY mention with trailing whitespace", async () => {
+    vi.mocked(countActiveDescendantRuns).mockReturnValue(0);
+    vi.mocked(isLikelyInterimCronMessage).mockReturnValue(false);
+
+    const params = makeBaseParams({
+      synthesizedText: "Use NO_REPLY when nothing actionable changed.\n",
+    });
+    const state = await dispatchCronDelivery(params);
+
+    expect(state.deliveryAttempted).toBe(true);
+    expect(state.delivered).toBe(true);
+    expect(deliverOutboundPayloads).toHaveBeenCalledTimes(1);
+  });
+
+  it("drops only the payload with trailing NO_REPLY in a multi-payload direct delivery", async () => {
+    vi.mocked(countActiveDescendantRuns).mockReturnValue(0);
+    vi.mocked(isLikelyInterimCronMessage).mockReturnValue(false);
+
+    const params = makeBaseParams({ synthesizedText: undefined });
+    params.deliveryPayloads = [
+      { text: "Working on it..." },
+      { text: "Final weather summary\n\nNO_REPLY" },
+    ];
+    params.summary = "Working on it...";
+    params.outputText = "Working on it...";
+
+    const state = await dispatchCronDelivery(params);
+
+    expect(state.deliveryAttempted).toBe(true);
+    expect(state.delivered).toBe(true);
+    expect(deliverOutboundPayloads).toHaveBeenCalledTimes(1);
+    expect(deliverOutboundPayloads).toHaveBeenCalledWith(
+      expect.objectContaining({
+        payloads: [{ text: "Working on it..." }],
+      }),
+    );
+  });
 });
diff --git a/src/cron/isolated-agent/delivery-dispatch.ts b/src/cron/isolated-agent/delivery-dispatch.ts
index f7e081bc895..fe5e7e8513d 100644
--- a/src/cron/isolated-agent/delivery-dispatch.ts
+++ b/src/cron/isolated-agent/delivery-dispatch.ts
@@ -1,5 +1,11 @@
 import type { ReplyPayload } from "../../auto-reply/reply-payload.js";
-import { isSilentReplyText, stripSilentToken, SILENT_REPLY_TOKEN } from "../../auto-reply/tokens.js";
+import {
+  isSilentReplyText,
+  SILENT_REPLY_TOKEN,
+  startsWithSilentToken,
+  stripLeadingSilentToken,
+  stripSilentToken,
+} from "../../auto-reply/tokens.js";
 import type { CliDeps } from "../../cli/outbound-send-deps.js";
 import {
   resolveAgentMainSessionKey,
@@ -10,6 +16,7 @@ import { sleepWithAbort } from "../../infra/backoff.js";
 import { formatErrorMessage } from "../../infra/errors.js";
 import type { OutboundDeliveryResult } from "../../infra/outbound/deliver.js";
 import { normalizeTargetForProvider } from "../../infra/outbound/target-normalization.js";
+import { hasReplyPayloadContent } from "../../interactive/payload.js";
 import {
   normalizeLowercaseStringOrEmpty,
   normalizeOptionalLowercaseString,
@@ -18,7 +25,7 @@ import {
 import { hasScheduledNextRunAtMs } from "../service/jobs.js";
 import type { CronJob, CronRunTelemetry } from "../types.js";
 import type { DeliveryTargetResolution } from "./delivery-target.js";
-import { pickSummaryFromOutput } from "./helpers.js";
+import { pickLastNonEmptyTextFromPayloads, pickSummaryFromOutput } from "./helpers.js";
 import type { RunCronAgentTurnResult } from "./run.types.js";
 import { expectsSubagentFollowup, isLikelyInterimCronMessage } from "./subagent-followup-hints.js";
 
@@ -27,6 +34,39 @@ function normalizeDeliveryTarget(channel: string, to: string): string {
   return normalizeTargetForProvider(channel, toTrimmed) ?? toTrimmed;
 }
 
+type NormalizedSilentReplyText = {
+  text: string | undefined;
+  strippedTrailingSilentToken: boolean;
+};
+
+function normalizeSilentReplyText(text: string | undefined): NormalizedSilentReplyText {
+  if (!text) {
+    return { text, strippedTrailingSilentToken: false };
+  }
+  if (isSilentReplyText(text, SILENT_REPLY_TOKEN)) {
+    return { text: undefined, strippedTrailingSilentToken: false };
+  }
+
+  let next = text;
+  const hasLeadingSilentToken = startsWithSilentToken(next, SILENT_REPLY_TOKEN);
+  if (hasLeadingSilentToken) {
+    next = stripLeadingSilentToken(next, SILENT_REPLY_TOKEN);
+  }
+
+  let strippedTrailingSilentToken = false;
+  if (hasLeadingSilentToken || next.toLowerCase().includes(SILENT_REPLY_TOKEN.toLowerCase())) {
+    const trimmedBefore = next.trim();
+    const stripped = stripSilentToken(next, SILENT_REPLY_TOKEN);
+    strippedTrailingSilentToken = stripped !== trimmedBefore;
+    next = stripped;
+  }
+
+  if (!next.trim() || isSilentReplyText(next, SILENT_REPLY_TOKEN)) {
+    return { text: undefined, strippedTrailingSilentToken };
+  }
+  return { text: next, strippedTrailingSilentToken };
+}
+
 export function matchesMessagingToolDeliveryTarget(
   target: { provider?: string; to?: string; accountId?: string },
   delivery: { channel?: string; to?: string; accountId?: string },
@@ -293,9 +333,12 @@ async function queueCronAwarenessSystemEvent(params: {
   deliveryIdempotencyKey: string;
   outputText?: string;
   synthesizedText?: string;
+  deliveryPayloads?: ReplyPayload[];
 }): Promise<void> {
-  const text =
-    normalizeOptionalString(params.outputText) ?? normalizeOptionalString(params.synthesizedText);
+  const text = params.deliveryPayloads
+    ? pickLastNonEmptyTextFromPayloads(params.deliveryPayloads)
+    : (normalizeOptionalString(params.outputText) ??
+      normalizeOptionalString(params.synthesizedText));
   if (!text) {
     return;
   }
@@ -462,21 +505,18 @@ export async function dispatchCronDelivery(
           : synthesizedText
             ? [{ text: synthesizedText }]
             : [];
-      // Suppress NO_REPLY sentinel so it never leaks to external channels.
-      // Also suppress payloads where the agent appended a trailing NO_REPLY
-      // after other text (e.g. "summary...\n\nNO_REPLY") — the token signals
-      // "do not deliver" regardless of preceding content.
-      const payloadsForDelivery = rawPayloads.filter((p) => {
-        const text = p.text ?? "";
-        if (isSilentReplyText(text, SILENT_REPLY_TOKEN)) {
-          return false;
-        }
-        // Case-insensitive trailing check: uppercase before stripping since
-        // stripSilentToken's regex is case-sensitive.
-        const upper = text.toUpperCase();
-        const stripped = stripSilentToken(upper, SILENT_REPLY_TOKEN);
-        return stripped === upper.trim();
-      });
+      const payloadsForDelivery = rawPayloads
+        .map((p) => {
+          if (!p.text) {
+            return p;
+          }
+          const normalized = normalizeSilentReplyText(p.text);
+          return {
+            ...p,
+            text: normalized.strippedTrailingSilentToken ? undefined : normalized.text,
+          };
+        })
+        .filter((p) => hasReplyPayloadContent(p, { trimText: true }));
       if (payloadsForDelivery.length === 0) {
         return await finishSilentReplyDelivery();
       }
@@ -583,6 +623,7 @@ export async function dispatchCronDelivery(
           deliveryIdempotencyKey,
           outputText,
           synthesizedText,
+          deliveryPayloads: payloadsForDelivery,
         });
       }
       if (delivered) {
@@ -700,17 +741,15 @@ export async function dispatchCronDelivery(
         ...params.telemetry,
       });
     }
-    // Suppress delivery when synthesizedText is (or ends with) NO_REPLY.
-    // isSilentReplyText handles case-insensitive exact matches (e.g. "No_Reply");
-    // stripSilentToken catches trailing tokens after other text.
-    if (isSilentReplyText(synthesizedText, SILENT_REPLY_TOKEN)) {
-      return await finishSilentReplyDelivery();
-    }
-    const upperSynthesized = synthesizedText.toUpperCase();
-    const strippedSynthesized = stripSilentToken(upperSynthesized, SILENT_REPLY_TOKEN);
-    if (strippedSynthesized !== upperSynthesized.trim()) {
+    const normalizedSynthesizedText = normalizeSilentReplyText(synthesizedText);
+    if (
+      normalizedSynthesizedText.text === undefined ||
+      normalizedSynthesizedText.strippedTrailingSilentToken
+    ) {
       return await finishSilentReplyDelivery();
     }
+    synthesizedText = normalizedSynthesizedText.text;
+    outputText = synthesizedText;
     if (params.isAborted()) {
       return params.withRunSession({
         status: "error",