diff --git a/CHANGELOG.md b/CHANGELOG.md
index 91c1d61d7b7..bb904f69b7f 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -31,6 +31,7 @@ Docs: https://docs.openclaw.ai
 - Gateway/pairing: shared-secret loopback CLI clients now silently auto-approve `metadata-upgrade` pairing (platform / device family refresh) instead of being disconnected with `1008 pairing required`. This matches the scope-upgrade and role-upgrade behavior added in #69431 and unblocks non-interactive CLI automation when a paired-device record has a stale platform string (e.g. device key replicated across hosts, install migrated between OSes, or platform-string format changed between OpenClaw versions). Browser / Control-UI clients keep the existing approval-required flow for metadata changes.
 - Gateway/pairing: treat any forwarded-header evidence (`Forwarded`, `X-Forwarded-*`, or `X-Real-IP`) as proxied WebSocket traffic before pairing locality checks, so reverse-proxy topologies cannot use the loopback shared-secret helper auto-pairing path.
 - Agents/OpenAI: treat exact `NO_REPLY` assistant output as a deliberate silent reply in embedded runs, so GPT-5.4 turns with signed reasoning plus a silent final no longer surface a false incomplete-turn error.
+- Auto-reply/streaming: preserve streamed reply directives through chunk boundaries and phase-aware `final_answer` delivery, so split `MEDIA:<path>` lines, voice tags, and reply targets reach channel delivery instead of leaking as text or being dropped. (#70243) Thanks @zqchris.
 - Gateway/pairing webchat: render `/pair qr` replies as structured media instead of raw markdown text, preserve inline reply threading and silent-control handling on media replies, avoid persisting sensitive QR images into transcript history, and keep local webchat media embedding behind internal-only trust markers. (#70047) Thanks @BunsDev.
 - Codex harness: default app-server runs to unchained local execution, so OpenAI heartbeats can use network and shell tools without stalling behind native Codex approvals or the workspace-write sandbox.
 - Codex harness: apply the GPT-5 behavior and heartbeat prompt overlay to native Codex app-server runs, so `codex/gpt-5.x` sessions get the same follow-through, tool-use, and proactive heartbeat guidance as OpenAI GPT-5 runs.
diff --git a/src/agents/pi-embedded-subscribe.handlers.messages.test.ts b/src/agents/pi-embedded-subscribe.handlers.messages.test.ts
index db315eca0d7..37151f0fbba 100644
--- a/src/agents/pi-embedded-subscribe.handlers.messages.test.ts
+++ b/src/agents/pi-embedded-subscribe.handlers.messages.test.ts
@@ -1,12 +1,15 @@
 import { describe, expect, it, vi } from "vitest";
+import { createStreamingDirectiveAccumulator } from "../auto-reply/reply/streaming-directives.js";
 import { createInlineCodeState } from "../markdown/code-spans.js";
 import {
   buildAssistantStreamData,
+  consumePendingAssistantReplyDirectivesIntoReply,
   consumePendingToolMediaIntoReply,
   consumePendingToolMediaReply,
   handleMessageEnd,
   handleMessageUpdate,
   hasAssistantVisibleReply,
+  recordPendingAssistantReplyDirectives,
   resolveSilentReplyFallbackText,
 } from "./pi-embedded-subscribe.handlers.messages.js";
 import type { EmbeddedPiSubscribeContext } from "./pi-embedded-subscribe.handlers.types.js";
@@ -24,6 +27,8 @@ function createMessageUpdateContext(
     resetAssistantMessageState?: ReturnType<typeof vi.fn>;
     debug?: ReturnType<typeof vi.fn>;
     shouldEmitPartialReplies?: boolean;
+    consumePartialReplyDirectives?: ReturnType<typeof vi.fn>;
+    state?: Record<string, unknown>;
   } = {},
 ) {
   return {
@@ -53,11 +58,13 @@ function createMessageUpdateContext(
       assistantMessageIndex: 0,
       lastAssistantStreamItemId: undefined,
       assistantTexts: [],
+      pendingAssistantReplyDirectives: undefined,
+      ...params.state,
     },
     log: { debug: params.debug ?? vi.fn() },
     noteLastAssistant: vi.fn(),
     stripBlockTags: (text: string) => text,
-    consumePartialReplyDirectives: vi.fn(() => null),
+    consumePartialReplyDirectives: params.consumePartialReplyDirectives ?? vi.fn(() => null),
     emitReasoningStream: vi.fn(),
     flushBlockReplyBuffer: params.flushBlockReplyBuffer ?? vi.fn(),
     resetAssistantMessageState: params.resetAssistantMessageState ?? vi.fn(),
@@ -194,6 +201,54 @@ describe("buildAssistantStreamData", () => {
   });
 });
 
+describe("pending assistant reply directives", () => {
+  it("merges directive metadata into the next non-reasoning block reply", () => {
+    const state = { pendingAssistantReplyDirectives: undefined };
+
+    recordPendingAssistantReplyDirectives(state, {
+      text: "",
+      mediaUrls: ["/tmp/reply.ogg"],
+      replyToCurrent: true,
+      replyToTag: true,
+      audioAsVoice: true,
+      isSilent: false,
+    });
+
+    expect(
+      consumePendingAssistantReplyDirectivesIntoReply(state, {
+        text: "Done.",
+      }),
+    ).toEqual({
+      text: "Done.",
+      mediaUrls: ["/tmp/reply.ogg"],
+      audioAsVoice: true,
+      replyToId: undefined,
+      replyToTag: true,
+      replyToCurrent: true,
+    });
+    expect(state.pendingAssistantReplyDirectives).toBeUndefined();
+  });
+
+  it("does not consume pending directive metadata on reasoning replies", () => {
+    const state = {
+      pendingAssistantReplyDirectives: {
+        mediaUrls: ["/tmp/reply.png"],
+      },
+    };
+
+    expect(
+      consumePendingAssistantReplyDirectivesIntoReply(state, {
+        text: "Thinking...",
+        isReasoning: true,
+      }),
+    ).toEqual({
+      text: "Thinking...",
+      isReasoning: true,
+    });
+    expect(state.pendingAssistantReplyDirectives?.mediaUrls).toEqual(["/tmp/reply.png"]);
+  });
+});
+
 describe("handleMessageUpdate", () => {
   it("treats phased textSignature item changes as assistant-message boundaries", () => {
     const flushBlockReplyBuffer = vi.fn();
@@ -244,6 +299,54 @@ describe("handleMessageUpdate", () => {
     expect(onAssistantMessageStart).toHaveBeenCalledTimes(1);
     expect(context.state.lastAssistantStreamItemId).toBe("item-2");
   });
+
+  it("preserves phase-aware media, voice, and reply directives for block delivery", () => {
+    const accumulator = createStreamingDirectiveAccumulator();
+    const ctx = createMessageUpdateContext({
+      consumePartialReplyDirectives: vi.fn((text: string, options?: { final?: boolean }) =>
+        accumulator.consume(text, options),
+      ),
+      state: {
+        blockReplyBreak: "message_end",
+      },
+    });
+    const replyText = "Done.\n\n[[reply_to_current]]\n[[audio_as_voice]]\nMEDIA:/tmp/reply.ogg";
+
+    handleMessageUpdate(
+      ctx,
+      createTextUpdateEvent({
+        type: "text_delta",
+        text: replyText,
+        id: "item-final",
+        signaturePhase: "final_answer",
+        partialPhase: "final_answer",
+      }),
+    );
+    handleMessageUpdate(
+      ctx,
+      createTextUpdateEvent({
+        type: "text_end",
+        text: replyText,
+        id: "item-final",
+        signaturePhase: "final_answer",
+        partialPhase: "final_answer",
+      }),
+    );
+
+    expect(ctx.state.blockBuffer).toBe("Done.");
+    expect(
+      consumePendingAssistantReplyDirectivesIntoReply(ctx.state, {
+        text: "Done.",
+      }),
+    ).toEqual({
+      text: "Done.",
+      mediaUrls: ["/tmp/reply.ogg"],
+      audioAsVoice: true,
+      replyToId: undefined,
+      replyToTag: true,
+      replyToCurrent: true,
+    });
+  });
 });
 
 describe("consumePendingToolMediaIntoReply", () => {
diff --git a/src/agents/pi-embedded-subscribe.handlers.messages.ts b/src/agents/pi-embedded-subscribe.handlers.messages.ts
index eb8819b3c8b..11859f7d62d 100644
--- a/src/agents/pi-embedded-subscribe.handlers.messages.ts
+++ b/src/agents/pi-embedded-subscribe.handlers.messages.ts
@@ -1,7 +1,11 @@
 import type { AgentEvent, AgentMessage } from "@mariozechner/pi-agent-core";
 import type { AssistantMessage } from "@mariozechner/pi-ai";
 import { resolveSendableOutboundReplyParts } from "openclaw/plugin-sdk/reply-payload";
-import { parseReplyDirectives } from "../auto-reply/reply/reply-directives.js";
+import {
+  parseReplyDirectives,
+  type ReplyDirectiveParseResult,
+} from "../auto-reply/reply/reply-directives.js";
+import { splitTrailingDirective } from "../auto-reply/reply/streaming-directives.js";
 import { isSilentReplyText, SILENT_REPLY_TOKEN } from "../auto-reply/tokens.js";
 import { emitAgentEvent } from "../infra/agent-events.js";
 import { createInlineCodeState } from "../markdown/code-spans.js";
@@ -33,21 +37,6 @@ import {
   promoteThinkingTagsToBlocks,
 } from "./pi-embedded-utils.js";
 
-const stripTrailingDirective = (text: string): string => {
-  const openIndex = text.lastIndexOf("[[");
-  if (openIndex < 0) {
-    if (text.endsWith("[")) {
-      return text.slice(0, -1);
-    }
-    return text;
-  }
-  const closeIndex = text.indexOf("]]", openIndex + 2);
-  if (closeIndex >= 0) {
-    return text;
-  }
-  return text.slice(0, openIndex);
-};
-
 function shouldSuppressAssistantVisibleOutput(message: AgentMessage | undefined): boolean {
   return resolveAssistantMessagePhase(message) === "commentary";
 }
@@ -242,6 +231,88 @@ export function consumePendingToolMediaReply(
   return payload;
 }
 
+function hasReplyDirectiveMetadata(parsed: ReplyDirectiveParseResult | null | undefined): boolean {
+  return Boolean(
+    parsed &&
+    ((parsed.mediaUrls?.length ?? 0) > 0 ||
+      parsed.audioAsVoice ||
+      parsed.replyToId ||
+      parsed.replyToTag ||
+      parsed.replyToCurrent),
+  );
+}
+
+function hasReplyDirectiveMetadataResult(
+  parsed: ReplyDirectiveParseResult | null | undefined,
+): parsed is ReplyDirectiveParseResult {
+  return hasReplyDirectiveMetadata(parsed);
+}
+
+function mergeReplyDirectiveResults(
+  first: ReplyDirectiveParseResult | null | undefined,
+  second: ReplyDirectiveParseResult | null | undefined,
+): ReplyDirectiveParseResult | null {
+  if (!first) {
+    return second ?? null;
+  }
+  if (!second) {
+    return first;
+  }
+  const mediaUrls = Array.from(new Set([...(first.mediaUrls ?? []), ...(second.mediaUrls ?? [])]));
+  return {
+    text: `${first.text ?? ""}${second.text ?? ""}`,
+    mediaUrls: mediaUrls.length ? mediaUrls : undefined,
+    mediaUrl: mediaUrls[0] ?? first.mediaUrl ?? second.mediaUrl,
+    replyToId: second.replyToId ?? first.replyToId,
+    replyToCurrent: first.replyToCurrent || second.replyToCurrent,
+    replyToTag: first.replyToTag || second.replyToTag,
+    audioAsVoice: first.audioAsVoice || second.audioAsVoice || undefined,
+    isSilent: first.isSilent || second.isSilent,
+  };
+}
+
+export function recordPendingAssistantReplyDirectives(
+  state: Pick<EmbeddedPiSubscribeState, "pendingAssistantReplyDirectives">,
+  parsed: ReplyDirectiveParseResult | null | undefined,
+) {
+  if (!hasReplyDirectiveMetadataResult(parsed)) {
+    return;
+  }
+  const current = state.pendingAssistantReplyDirectives;
+  const mediaUrls = Array.from(
+    new Set([...(current?.mediaUrls ?? []), ...(parsed.mediaUrls ?? [])]),
+  );
+  state.pendingAssistantReplyDirectives = {
+    mediaUrls: mediaUrls.length ? mediaUrls : undefined,
+    audioAsVoice: current?.audioAsVoice || parsed?.audioAsVoice || undefined,
+    replyToId: parsed?.replyToId ?? current?.replyToId,
+    replyToTag: current?.replyToTag || parsed.replyToTag || undefined,
+    replyToCurrent: current?.replyToCurrent || parsed.replyToCurrent || undefined,
+  };
+}
+
+export function consumePendingAssistantReplyDirectivesIntoReply(
+  state: Pick<EmbeddedPiSubscribeState, "pendingAssistantReplyDirectives">,
+  payload: BlockReplyPayload,
+): BlockReplyPayload {
+  if (payload.isReasoning || !state.pendingAssistantReplyDirectives) {
+    return payload;
+  }
+  const pending = state.pendingAssistantReplyDirectives;
+  const mediaUrls = Array.from(
+    new Set([...(payload.mediaUrls ?? []), ...(pending.mediaUrls ?? [])]),
+  );
+  state.pendingAssistantReplyDirectives = undefined;
+  return {
+    ...payload,
+    mediaUrls: mediaUrls.length ? mediaUrls : undefined,
+    audioAsVoice: payload.audioAsVoice || pending.audioAsVoice || undefined,
+    replyToId: payload.replyToId ?? pending.replyToId,
+    replyToTag: Boolean(payload.replyToTag || pending.replyToTag) || undefined,
+    replyToCurrent: Boolean(payload.replyToCurrent || pending.replyToCurrent) || undefined,
+  };
+}
+
 export function hasAssistantVisibleReply(params: {
   text?: string;
   mediaUrls?: string[];
@@ -431,10 +502,16 @@ export function handleMessageUpdate(
       emitReasoningEnd(ctx);
     }
     const parsedDelta = visibleDelta ? ctx.consumePartialReplyDirectives(visibleDelta) : null;
-    const parsedFull = parseReplyDirectives(stripTrailingDirective(next));
+    const finalParsedDelta =
+      evtType === "text_end" ? ctx.consumePartialReplyDirectives("", { final: true }) : null;
+    const parsedStreamDirectives = mergeReplyDirectiveResults(parsedDelta, finalParsedDelta);
+    if (shouldUsePhaseAwareBlockReply) {
+      recordPendingAssistantReplyDirectives(ctx.state, parsedStreamDirectives);
+    }
+    const parsedFull = parseReplyDirectives(splitTrailingDirective(next).text);
     const cleanedText = parsedFull.text;
-    const { mediaUrls, hasMedia } = resolveSendableOutboundReplyParts(parsedDelta ?? {});
-    const hasAudio = Boolean(parsedDelta?.audioAsVoice);
+    const { mediaUrls, hasMedia } = resolveSendableOutboundReplyParts(parsedStreamDirectives ?? {});
+    const hasAudio = Boolean(parsedStreamDirectives?.audioAsVoice);
     const previousCleaned = ctx.state.lastStreamedAssistantCleaned ?? "";
 
     let shouldEmit = false;
@@ -562,7 +639,9 @@ export function handleMessageEnd(
       : "";
   const formattedReasoning = rawThinking ? formatReasoningMessage(rawThinking) : "";
   const trimmedText = text.trim();
-  const parsedText = trimmedText ? parseReplyDirectives(stripTrailingDirective(trimmedText)) : null;
+  const parsedText = trimmedText
+    ? parseReplyDirectives(splitTrailingDirective(trimmedText, { final: true }).text)
+    : null;
   let cleanedText = parsedText?.text ?? "";
   let { mediaUrls, hasMedia } = resolveSendableOutboundReplyParts(parsedText ?? {});
 
@@ -695,6 +774,14 @@ export function handleMessageEnd(
     if (hasBufferedBlockReply && ctx.blockChunker?.hasBuffered()) {
       ctx.blockChunker.drain({ force: true, emit: ctx.emitBlockChunk });
       ctx.blockChunker.reset();
+      // Final-flush the streaming directive accumulator so any partial
+      // directive tail held back by splitTrailingDirective (for example a
+      // trailing `MEDIA:<path>` that arrived without a closing newline)
+      // gets emitted here. Without this, a reply ending in a directive
+      // line whose URL is complete but un-terminated would sit in
+      // pendingTail forever and the attachment would be silently dropped
+      // on the message_end / blockReplyChunking path.
+      emitSplitResultAsBlockReply(ctx.consumeReplyDirectives("", { final: true }));
     } else if (text !== ctx.state.lastBlockReplyText) {
       // Guard: for text_end channels, if text_end already delivered content
       // (lastBlockReplyText is set), skip this safety send. The text comparison
diff --git a/src/agents/pi-embedded-subscribe.handlers.types.ts b/src/agents/pi-embedded-subscribe.handlers.types.ts
index e0e544e4b7b..f541578ec23 100644
--- a/src/agents/pi-embedded-subscribe.handlers.types.ts
+++ b/src/agents/pi-embedded-subscribe.handlers.types.ts
@@ -82,6 +82,10 @@ export type EmbeddedPiSubscribeState = {
   pendingToolMediaUrls: string[];
   pendingToolAudioAsVoice: boolean;
   pendingToolTrustedLocalMedia: boolean;
+  pendingAssistantReplyDirectives?: Pick<
+    BlockReplyPayload,
+    "mediaUrls" | "audioAsVoice" | "replyToId" | "replyToTag" | "replyToCurrent"
+  >;
   deterministicApprovalPromptPending: boolean;
   deterministicApprovalPromptSent: boolean;
   lastAssistant?: AgentMessage;
diff --git a/src/agents/pi-embedded-subscribe.subscribe-embedded-pi-session.subscribeembeddedpisession.test.ts b/src/agents/pi-embedded-subscribe.subscribe-embedded-pi-session.subscribeembeddedpisession.test.ts
index 2b069a4c001..58ef500b83f 100644
--- a/src/agents/pi-embedded-subscribe.subscribe-embedded-pi-session.subscribeembeddedpisession.test.ts
+++ b/src/agents/pi-embedded-subscribe.subscribe-embedded-pi-session.subscribeembeddedpisession.test.ts
@@ -446,7 +446,7 @@ describe("subscribeEmbeddedPiSession", () => {
     expect(payloads).toHaveLength(1);
   });
 
-  it("emits a replacement snapshot when cleaned text rewinds mid-stream", () => {
+  it("emits one cleaned media snapshot when a streamed MEDIA line resolves to caption text", () => {
     const { emit, onAgentEvent } = createAgentEventHarness();
 
     emit({ type: "message_start", message: { role: "assistant" } });
@@ -454,20 +454,26 @@ describe("subscribeEmbeddedPiSession", () => {
     emitAssistantTextDelta(emit, " https://example.com/a.png\nCaption");
 
     const payloads = extractAgentEventPayloads(onAgentEvent.mock.calls);
-    expect(payloads).toHaveLength(2);
-    expect(payloads[0]?.text).toBe("MEDIA:");
-    expect(payloads[0]?.delta).toBe("MEDIA:");
+    expect(payloads).toHaveLength(1);
+    expect(payloads[0]?.text).toBe("Caption");
+    expect(payloads[0]?.delta).toBe("Caption");
     expect(payloads[0]?.replace).toBeUndefined();
-    expect(payloads[1]?.text).toBe("Caption");
-    expect(payloads[1]?.delta).toBe("");
-    expect(payloads[1]?.replace).toBe(true);
+    expect(payloads[0]?.mediaUrls).toEqual(["https://example.com/a.png"]);
   });
 
-  it("emits agent events when media arrives without text", () => {
+  it("emits agent events when media-only text is finalized", () => {
     const { emit, onAgentEvent } = createAgentEventHarness();
 
     emit({ type: "message_start", message: { role: "assistant" } });
     emitAssistantTextDelta(emit, "MEDIA: https://example.com/a.png");
+    emit({
+      type: "message_update",
+      message: { role: "assistant" },
+      assistantMessageEvent: {
+        type: "text_end",
+        content: "MEDIA: https://example.com/a.png",
+      },
+    });
 
     const payloads = extractAgentEventPayloads(onAgentEvent.mock.calls);
     expect(payloads).toHaveLength(1);
diff --git a/src/agents/pi-embedded-subscribe.ts b/src/agents/pi-embedded-subscribe.ts
index 3197f575f2c..c17376de978 100644
--- a/src/agents/pi-embedded-subscribe.ts
+++ b/src/agents/pi-embedded-subscribe.ts
@@ -21,7 +21,10 @@ import {
 } from "./pi-embedded-runner/replay-state.js";
 import type { EmbeddedRunLivenessState } from "./pi-embedded-runner/types.js";
 import { createEmbeddedPiSessionEventHandler } from "./pi-embedded-subscribe.handlers.js";
-import { consumePendingToolMediaIntoReply } from "./pi-embedded-subscribe.handlers.messages.js";
+import {
+  consumePendingAssistantReplyDirectivesIntoReply,
+  consumePendingToolMediaIntoReply,
+} from "./pi-embedded-subscribe.handlers.messages.js";
 import type {
   EmbeddedPiSubscribeContext,
   EmbeddedPiSubscribeState,
@@ -124,6 +127,7 @@ export function subscribeEmbeddedPiSession(params: SubscribeEmbeddedPiSessionPar
     pendingToolMediaUrls: initialPendingToolMediaUrls,
     pendingToolAudioAsVoice: false,
     pendingToolTrustedLocalMedia: false,
+    pendingAssistantReplyDirectives: undefined,
     deterministicApprovalPromptPending: false,
     deterministicApprovalPromptSent: false,
   };
@@ -184,7 +188,8 @@ export function subscribeEmbeddedPiSession(params: SubscribeEmbeddedPiSessionPar
     payload: BlockReplyPayload,
     options?: { assistantMessageIndex?: number },
   ) => {
-    emitBlockReplySafely(consumePendingToolMediaIntoReply(state, payload), options);
+    const withAssistantDirectives = consumePendingAssistantReplyDirectivesIntoReply(state, payload);
+    emitBlockReplySafely(consumePendingToolMediaIntoReply(state, withAssistantDirectives), options);
   };
 
   const resetAssistantMessageState = (nextAssistantTextBaseline: number) => {
@@ -213,6 +218,7 @@ export function subscribeEmbeddedPiSession(params: SubscribeEmbeddedPiSessionPar
     state.lastAssistantTextNormalized = undefined;
     state.lastAssistantTextTrimmed = undefined;
     state.assistantTextBaseline = nextAssistantTextBaseline;
+    state.pendingAssistantReplyDirectives = undefined;
   };
 
   const rememberAssistantText = (text: string) => {
@@ -710,6 +716,7 @@ export function subscribeEmbeddedPiSession(params: SubscribeEmbeddedPiSessionPar
     state.pendingMessagingMediaUrls.clear();
     state.pendingToolMediaUrls = [];
     state.pendingToolAudioAsVoice = false;
+    state.pendingAssistantReplyDirectives = undefined;
     state.deterministicApprovalPromptPending = false;
     state.deterministicApprovalPromptSent = false;
     state.replayState = mergeEmbeddedRunReplayState(state.replayState, params.initialReplayState);
diff --git a/src/auto-reply/reply/reply-utils.test.ts b/src/auto-reply/reply/reply-utils.test.ts
index 09a008b74f0..6c9f1fa82bc 100644
--- a/src/auto-reply/reply/reply-utils.test.ts
+++ b/src/auto-reply/reply/reply-utils.test.ts
@@ -10,7 +10,10 @@ import {
   hasTemplateVariables,
   resolveResponsePrefixTemplate,
 } from "./response-prefix-template.js";
-import { createStreamingDirectiveAccumulator } from "./streaming-directives.js";
+import {
+  createStreamingDirectiveAccumulator,
+  splitTrailingDirective,
+} from "./streaming-directives.js";
 import { createMockTypingController } from "./test-helpers.js";
 import { createTypingSignaler, resolveTypingMode } from "./typing-mode.js";
 import { createTypingController } from "./typing.js";
@@ -989,6 +992,15 @@ describe("createStreamingDirectiveAccumulator", () => {
     expect(result?.replyToCurrent).toBe(true);
   });
 
+  it("handles reply tags split before the second bracket", () => {
+    const accumulator = createStreamingDirectiveAccumulator();
+    expect(accumulator.consume("[")).toBeNull();
+
+    const result = accumulator.consume("[reply_to_current]] Yo");
+    expect(result?.text).toBe("Yo");
+    expect(result?.replyToCurrent).toBe(true);
+  });
+
   it("propagates explicit reply ids across current and subsequent chunks", () => {
     const accumulator = createStreamingDirectiveAccumulator();
 
@@ -1033,6 +1045,135 @@ describe("createStreamingDirectiveAccumulator", () => {
 
     expect(result?.text).toBe("NO_REPLY: explanation");
   });
+
+  it("reassembles MEDIA: directives split between the token and the colon", () => {
+    const accumulator = createStreamingDirectiveAccumulator();
+
+    const first = accumulator.consume("这次直接发图。\n\nMEDIA");
+    expect(first?.text).toBe("这次直接发图。");
+    expect(first?.mediaUrls).toBeUndefined();
+
+    const second = accumulator.consume(":/tmp/spy-family.png");
+    expect(second).toBeNull();
+
+    const finalResult = accumulator.consume("", { final: true });
+    expect(finalResult?.mediaUrls).toEqual(["/tmp/spy-family.png"]);
+    expect((finalResult?.text ?? "").includes("MEDIA")).toBe(false);
+  });
+
+  it("reassembles MEDIA: directives split inside the URL path", () => {
+    const accumulator = createStreamingDirectiveAccumulator();
+
+    const first = accumulator.consume("Preview below.\n\nMEDIA:/var/folders/tool-image");
+    expect(first?.text).toBe("Preview below.");
+    expect(first?.mediaUrls).toBeUndefined();
+
+    const second = accumulator.consume("-generation/cover.png");
+    expect(second).toBeNull();
+
+    const finalResult = accumulator.consume("", { final: true });
+    expect(finalResult?.mediaUrls).toEqual(["/var/folders/tool-image-generation/cover.png"]);
+  });
+
+  it("buffers partial MEDIA prefixes (M/ME/MED/MEDI) across chunk boundaries", () => {
+    for (const prefix of ["M", "ME", "MED", "MEDI"]) {
+      const accumulator = createStreamingDirectiveAccumulator();
+      const head = `Here is the file.\n\n${prefix}`;
+      const headResult = accumulator.consume(head);
+      expect(headResult?.text, `prefix=${prefix} head emits text`).toBe("Here is the file.");
+
+      const rest = `MEDIA:/tmp/file.png`.slice(prefix.length);
+      const restResult = accumulator.consume(rest);
+      expect(restResult, `prefix=${prefix} mid returns null`).toBeNull();
+
+      const finalResult = accumulator.consume("", { final: true });
+      expect(finalResult?.mediaUrls, `prefix=${prefix} final mediaUrls`).toEqual(["/tmp/file.png"]);
+    }
+  });
+
+  it("does not buffer a trailing letter that appears mid-line", () => {
+    const accumulator = createStreamingDirectiveAccumulator();
+
+    // "I am" ends in "m". The prefix guard only anchors to line-start (`^`
+    // or immediately after `\n`), so ordinary prose whose last character
+    // happens to be an `M|ME|MED|MEDI|MEDIA` letter stays in the emitted
+    // text.
+    const result = accumulator.consume("I am");
+    expect(result?.text).toBe("I am");
+    expect(result?.mediaUrls).toBeUndefined();
+  });
+
+  it("does not buffer prose that merely contains the token MEDIA:", () => {
+    const accumulator = createStreamingDirectiveAccumulator();
+
+    // Matches what upstream `splitMediaFromOutput` considers a directive:
+    // only lines whose trimmed start is `MEDIA:`. A line that merely
+    // contains "MEDIA:" mid-sentence is ordinary prose and must flush
+    // immediately — otherwise on a stream-item boundary (which may call
+    // `reset()` without a preceding `consume("", { final: true })`) the
+    // buffered prose would be silently dropped.
+    const result = accumulator.consume("See the MEDIA: section for details");
+    expect(result?.text).toBe("See the MEDIA: section for details");
+    expect(result?.mediaUrls).toBeUndefined();
+  });
+
+  it("still buffers an indented MEDIA directive line that is mid-stream", () => {
+    const accumulator = createStreamingDirectiveAccumulator();
+
+    // Upstream parser treats `line.trimStart().startsWith("MEDIA:")` as a
+    // directive, so the guard must also buffer the indented form across
+    // a chunk boundary.
+    const first = accumulator.consume("Preview:\n  MEDIA:/tmp/cover");
+    expect(first?.text).toBe("Preview:");
+    expect(first?.mediaUrls).toBeUndefined();
+
+    const second = accumulator.consume(".png");
+    expect(second).toBeNull();
+
+    const finalResult = accumulator.consume("", { final: true });
+    expect(finalResult?.mediaUrls).toEqual(["/tmp/cover.png"]);
+  });
+
+  it("does not rewrite mid-prose MEDIA into a directive across chunks", () => {
+    const accumulator = createStreamingDirectiveAccumulator();
+
+    // A chunk can legitimately end with `MEDIA` mid-sentence (e.g. "this
+    // uses legacy MEDIA"). A later chunk starting with `:` must NOT join
+    // with the buffered token to synthesize a `MEDIA:<rest>` directive —
+    // upstream `MEDIA_TOKEN_RE` captures `[^\n]+`, and treating the rest
+    // of that sentence as a media path would invent a media reply the
+    // agent never authored.
+    const first = accumulator.consume("The legacy pipeline uses MEDIA");
+    expect(first?.text).toBe("The legacy pipeline uses MEDIA");
+    expect(first?.mediaUrls).toBeUndefined();
+
+    const second = accumulator.consume(": kind=disk capacity=1TB");
+    expect(second?.text).toBe(": kind=disk capacity=1TB");
+    expect(second?.mediaUrls).toBeUndefined();
+  });
+
+  it("passes plain text through when there is no incomplete directive tail", () => {
+    const accumulator = createStreamingDirectiveAccumulator();
+
+    const result = accumulator.consume("Hello world.\nThis is a complete block.");
+    expect(result?.text).toBe("Hello world.\nThis is a complete block.");
+    expect(result?.mediaUrls).toBeUndefined();
+  });
+
+  it("keeps MEDIA directives that arrive in a single complete chunk working", () => {
+    const accumulator = createStreamingDirectiveAccumulator();
+
+    const result = accumulator.consume("Here it is.\n\nMEDIA:/tmp/complete.png\n");
+    expect(result?.text.includes("MEDIA")).toBe(false);
+    expect(result?.mediaUrls).toEqual(["/tmp/complete.png"]);
+  });
+
+  it("does not strip a complete final MEDIA line when parsing final text", () => {
+    expect(splitTrailingDirective("Here.\nMEDIA:/tmp/final.png", { final: true })).toEqual({
+      text: "Here.\nMEDIA:/tmp/final.png",
+      tail: "",
+    });
+  });
 });
 
 describe("extractShortModelName", () => {
diff --git a/src/auto-reply/reply/streaming-directives.ts b/src/auto-reply/reply/streaming-directives.ts
index 9feb194deaa..5fe4c9680e4 100644
--- a/src/auto-reply/reply/streaming-directives.ts
+++ b/src/auto-reply/reply/streaming-directives.ts
@@ -25,18 +25,84 @@ type ConsumeOptions = {
   silentToken?: string;
 };
 
-const splitTrailingDirective = (text: string): { text: string; tail: string } => {
+type SplitTrailingDirectiveOptions = {
+  final?: boolean;
+};
+
+// Holds back incomplete streaming-directive tails so parseChunk only ever sees
+// complete directives. Otherwise, upstream token boundaries can split markers
+// like `MEDIA:<path>` between chunks and cause the first half to be emitted as
+// plain text (e.g. the `MEDIA` token leaking into a channel reply while the
+// matching file path is silently dropped on the next chunk).
+export const splitTrailingDirective = (
+  text: string,
+  options: SplitTrailingDirectiveOptions = {},
+): { text: string; tail: string } => {
+  let bufferStart = text.length;
+
+  // 1. Unclosed `[[…` reply/audio directive tail.
   const openIndex = text.lastIndexOf("[[");
-  if (openIndex < 0) {
-    return { text, tail: "" };
-  }
-  const closeIndex = text.indexOf("]]", openIndex + 2);
-  if (closeIndex >= 0) {
+  if (openIndex >= 0 && text.indexOf("]]", openIndex + 2) < 0) {
+    if (openIndex < bufferStart) {
+      bufferStart = openIndex;
+    }
+  }
+  if (text.endsWith("[") && text.length - 1 < bufferStart) {
+    bufferStart = text.length - 1;
+  }
+
+  if (options.final) {
+    if (bufferStart >= text.length) {
+      return { text, tail: "" };
+    }
+
+    return {
+      text: text.slice(0, bufferStart),
+      tail: text.slice(bufferStart),
+    };
+  }
+
+  // 2. `MEDIA:` line without a trailing newline — the URL may still be
+  //    streaming. `splitMediaFromOutput` in src/media/parse.ts treats a
+  //    line as a media directive only when `line.trimStart()` begins with
+  //    `MEDIA:`, so we match the same shape here: only buffer when the
+  //    last line looks like an actual directive line (optional leading
+  //    whitespace, then `MEDIA:`). Prose such as
+  //    "See the MEDIA: section for details" does NOT qualify and is
+  //    flushed as ordinary text — otherwise it could sit in pendingTail
+  //    and be silently dropped if a stream-item boundary calls `reset()`
+  //    without a preceding `consume("", { final: true })`.
+  const lastNewline = text.lastIndexOf("\n");
+  const lastLine = lastNewline < 0 ? text : text.slice(lastNewline + 1);
+  if (/^\s*MEDIA:/i.test(lastLine)) {
+    const mediaLineStart = lastNewline < 0 ? 0 : lastNewline + 1;
+    if (mediaLineStart < bufferStart) {
+      bufferStart = mediaLineStart;
+    }
+  }
+
+  // 3. Trailing `M|ME|MED|MEDI|MEDIA` prefix (no colon yet) at the start of
+  //    a line — the next chunk might turn this into `MEDIA:<url>`. Only a
+  //    line-start anchor (`^` or immediately after `\n`) is accepted so
+  //    mid-prose tokens like "_M", "3ME", or "token MEDIA" are not
+  //    speculatively buffered and cannot accidentally be glued to a
+  //    following `:` into a synthetic directive. Matches the canonical
+  //    MEDIA directive placement (own line after `\n\n`).
+  const prefixMatch = text.match(/(?:^|\n)(MEDIA|MEDI|MED|ME|M)$/i);
+  if (prefixMatch) {
+    const prefixStart = text.length - prefixMatch[1].length;
+    if (prefixStart < bufferStart) {
+      bufferStart = prefixStart;
+    }
+  }
+
+  if (bufferStart >= text.length) {
     return { text, tail: "" };
   }
+
   return {
-    text: text.slice(0, openIndex),
-    tail: text.slice(openIndex),
+    text: text.slice(0, bufferStart),
+    tail: text.slice(bufferStart),
   };
 };