diff --git a/src/agents/pi-embedded-subscribe.handlers.tools.test.ts b/src/agents/pi-embedded-subscribe.handlers.tools.test.ts
index cff144d23a..473f6fdb8d 100644
--- a/src/agents/pi-embedded-subscribe.handlers.tools.test.ts
+++ b/src/agents/pi-embedded-subscribe.handlers.tools.test.ts
@@ -1,14 +1,14 @@
 import type { AgentEvent } from "@mariozechner/pi-agent-core";
 import { describe, expect, it, vi } from "vitest";
 import type { MessagingToolSend } from "./pi-embedded-messaging.js";
-import {
-  handleToolExecutionEnd,
-  handleToolExecutionStart,
-} from "./pi-embedded-subscribe.handlers.tools.js";
 import type {
   ToolCallSummary,
   ToolHandlerContext,
 } from "./pi-embedded-subscribe.handlers.types.js";
+import {
+  handleToolExecutionEnd,
+  handleToolExecutionStart,
+} from "./pi-embedded-subscribe.handlers.tools.js";
 
 type ToolExecutionStartEvent = Extract<AgentEvent, { type: "tool_execution_start" }>;
 type ToolExecutionEndEvent = Extract<AgentEvent, { type: "tool_execution_end" }>;
@@ -39,7 +39,7 @@ function createTestContext(): {
       toolSummaryById: new Set<string>(),
       pendingMessagingTargets: new Map<string, MessagingToolSend>(),
       pendingMessagingTexts: new Map<string, string>(),
-      pendingMessagingMediaUrls: new Map<string, string>(),
+      pendingMessagingMediaUrls: new Map<string, string[]>(),
       messagingToolSentTexts: [],
       messagingToolSentTextsNormalized: [],
       messagingToolSentMediaUrls: [],
@@ -145,19 +145,19 @@ describe("handleToolExecutionEnd cron.add commitment tracking", () => {
 });
 
 describe("messaging tool media URL tracking", () => {
-  it("tracks mediaUrl arg from messaging tool as pending", async () => {
+  it("tracks media arg from messaging tool as pending", async () => {
     const { ctx } = createTestContext();
 
     const evt: ToolExecutionStartEvent = {
       type: "tool_execution_start",
       toolName: "message",
       toolCallId: "tool-m1",
-      args: { action: "send", to: "channel:123", content: "hi", mediaUrl: "file:///img.jpg" },
+      args: { action: "send", to: "channel:123", content: "hi", media: "file:///img.jpg" },
     };
 
     await handleToolExecutionStart(ctx, evt);
 
-    expect(ctx.state.pendingMessagingMediaUrls.get("tool-m1")).toBe("file:///img.jpg");
+    expect(ctx.state.pendingMessagingMediaUrls.get("tool-m1")).toEqual(["file:///img.jpg"]);
   });
 
   it("commits pending media URL on tool success", async () => {
@@ -168,7 +168,7 @@ describe("messaging tool media URL tracking", () => {
       type: "tool_execution_start",
       toolName: "message",
       toolCallId: "tool-m2",
-      args: { action: "send", to: "channel:123", content: "hi", mediaUrl: "file:///img.jpg" },
+      args: { action: "send", to: "channel:123", content: "hi", media: "file:///img.jpg" },
     };
 
     await handleToolExecutionStart(ctx, startEvt);
@@ -188,6 +188,41 @@ describe("messaging tool media URL tracking", () => {
     expect(ctx.state.pendingMessagingMediaUrls.has("tool-m2")).toBe(false);
   });
 
+  it("commits mediaUrls from tool result payload", async () => {
+    const { ctx } = createTestContext();
+
+    const startEvt: ToolExecutionStartEvent = {
+      type: "tool_execution_start",
+      toolName: "message",
+      toolCallId: "tool-m2b",
+      args: { action: "send", to: "channel:123", content: "hi" },
+    };
+    await handleToolExecutionStart(ctx, startEvt);
+
+    const endEvt: ToolExecutionEndEvent = {
+      type: "tool_execution_end",
+      toolName: "message",
+      toolCallId: "tool-m2b",
+      isError: false,
+      result: {
+        content: [
+          {
+            type: "text",
+            text: JSON.stringify({
+              mediaUrls: ["file:///img-a.jpg", "file:///img-b.jpg"],
+            }),
+          },
+        ],
+      },
+    };
+    await handleToolExecutionEnd(ctx, endEvt);
+
+    expect(ctx.state.messagingToolSentMediaUrls).toEqual([
+      "file:///img-a.jpg",
+      "file:///img-b.jpg",
+    ]);
+  });
+
   it("trims messagingToolSentMediaUrls to 200 on commit (FIFO)", async () => {
     const { ctx } = createTestContext();
 
@@ -220,7 +255,7 @@ describe("messaging tool media URL tracking", () => {
       type: "tool_execution_start",
       toolName: "message",
       toolCallId: "tool-cap",
-      args: { action: "send", to: "channel:123", content: "hi", mediaUrl: "file:///img-new.jpg" },
+      args: { action: "send", to: "channel:123", content: "hi", media: "file:///img-new.jpg" },
     };
     await handleToolExecutionStart(ctx, startEvt);
 
@@ -247,7 +282,7 @@ describe("messaging tool media URL tracking", () => {
       type: "tool_execution_start",
       toolName: "message",
       toolCallId: "tool-m3",
-      args: { action: "send", to: "channel:123", content: "hi", mediaUrl: "file:///img.jpg" },
+      args: { action: "send", to: "channel:123", content: "hi", media: "file:///img.jpg" },
     };
 
     await handleToolExecutionStart(ctx, startEvt);
diff --git a/src/agents/pi-embedded-subscribe.handlers.tools.ts b/src/agents/pi-embedded-subscribe.handlers.tools.ts
index 2a9c1ce57f..d7bbbc9e07 100644
--- a/src/agents/pi-embedded-subscribe.handlers.tools.ts
+++ b/src/agents/pi-embedded-subscribe.handlers.tools.ts
@@ -1,13 +1,13 @@
 import type { AgentEvent } from "@mariozechner/pi-agent-core";
-import { emitAgentEvent } from "../infra/agent-events.js";
-import { getGlobalHookRunner } from "../plugins/hook-runner-global.js";
 import type { PluginHookAfterToolCallEvent } from "../plugins/types.js";
-import { normalizeTextForComparison } from "./pi-embedded-helpers.js";
-import { isMessagingTool, isMessagingToolSendAction } from "./pi-embedded-messaging.js";
 import type {
   ToolCallSummary,
   ToolHandlerContext,
 } from "./pi-embedded-subscribe.handlers.types.js";
+import { emitAgentEvent } from "../infra/agent-events.js";
+import { getGlobalHookRunner } from "../plugins/hook-runner-global.js";
+import { normalizeTextForComparison } from "./pi-embedded-helpers.js";
+import { isMessagingTool, isMessagingToolSendAction } from "./pi-embedded-messaging.js";
 import {
   extractToolErrorMessage,
   extractToolResultMediaPaths,
@@ -63,6 +63,71 @@ function extendExecMeta(toolName: string, args: unknown, meta?: string): string
   return meta ? `${meta} · ${suffix}` : suffix;
 }
 
+function pushUniqueMediaUrl(urls: string[], seen: Set<string>, value: unknown): void {
+  if (typeof value !== "string") {
+    return;
+  }
+  const normalized = value.trim();
+  if (!normalized || seen.has(normalized)) {
+    return;
+  }
+  seen.add(normalized);
+  urls.push(normalized);
+}
+
+function collectMessagingMediaUrlsFromRecord(record: Record<string, unknown>): string[] {
+  const urls: string[] = [];
+  const seen = new Set<string>();
+
+  pushUniqueMediaUrl(urls, seen, record.media);
+  pushUniqueMediaUrl(urls, seen, record.mediaUrl);
+  pushUniqueMediaUrl(urls, seen, record.path);
+  pushUniqueMediaUrl(urls, seen, record.filePath);
+
+  const mediaUrls = record.mediaUrls;
+  if (Array.isArray(mediaUrls)) {
+    for (const mediaUrl of mediaUrls) {
+      pushUniqueMediaUrl(urls, seen, mediaUrl);
+    }
+  }
+
+  return urls;
+}
+
+function collectMessagingMediaUrlsFromToolResult(result: unknown): string[] {
+  const urls: string[] = [];
+  const seen = new Set<string>();
+  const appendFromRecord = (value: unknown) => {
+    if (!value || typeof value !== "object") {
+      return;
+    }
+    const extracted = collectMessagingMediaUrlsFromRecord(value as Record<string, unknown>);
+    for (const url of extracted) {
+      if (seen.has(url)) {
+        continue;
+      }
+      seen.add(url);
+      urls.push(url);
+    }
+  };
+
+  appendFromRecord(result);
+  if (result && typeof result === "object") {
+    appendFromRecord((result as Record<string, unknown>).details);
+  }
+
+  const outputText = extractToolResultText(result);
+  if (outputText) {
+    try {
+      appendFromRecord(JSON.parse(outputText));
+    } catch {
+      // Ignore non-JSON tool output.
+    }
+  }
+
+  return urls;
+}
+
 export async function handleToolExecutionStart(
   ctx: ToolHandlerContext,
   evt: AgentEvent & { toolName: string; toolCallId: string; args: unknown },
@@ -145,10 +210,10 @@ export async function handleToolExecutionStart(
         ctx.state.pendingMessagingTexts.set(toolCallId, text);
         ctx.log.debug(`Tracking pending messaging text: tool=${toolName} len=${text.length}`);
       }
-      // Track media URL from messaging tool args (pending until tool_execution_end)
-      const mediaUrl = argsRecord.mediaUrl ?? argsRecord.path ?? argsRecord.filePath;
-      if (mediaUrl && typeof mediaUrl === "string") {
-        ctx.state.pendingMessagingMediaUrls.set(toolCallId, mediaUrl);
+      // Track media URLs from messaging tool args (pending until tool_execution_end).
+      const mediaUrls = collectMessagingMediaUrlsFromRecord(argsRecord);
+      if (mediaUrls.length > 0) {
+        ctx.state.pendingMessagingMediaUrls.set(toolCallId, mediaUrls);
       }
     }
   }
@@ -253,11 +318,22 @@ export async function handleToolExecutionEnd(
       ctx.trimMessagingToolSent();
     }
   }
-  const pendingMediaUrl = ctx.state.pendingMessagingMediaUrls.get(toolCallId);
-  if (pendingMediaUrl) {
-    ctx.state.pendingMessagingMediaUrls.delete(toolCallId);
-    if (!isToolError) {
-      ctx.state.messagingToolSentMediaUrls.push(pendingMediaUrl);
+  const pendingMediaUrls = ctx.state.pendingMessagingMediaUrls.get(toolCallId) ?? [];
+  ctx.state.pendingMessagingMediaUrls.delete(toolCallId);
+  const startArgs =
+    startData?.args && typeof startData.args === "object"
+      ? (startData.args as Record<string, unknown>)
+      : {};
+  const isMessagingSend =
+    pendingMediaUrls.length > 0 ||
+    (isMessagingTool(toolName) && isMessagingToolSendAction(toolName, startArgs));
+  if (!isToolError && isMessagingSend) {
+    const committedMediaUrls = [
+      ...pendingMediaUrls,
+      ...collectMessagingMediaUrlsFromToolResult(result),
+    ];
+    if (committedMediaUrls.length > 0) {
+      ctx.state.messagingToolSentMediaUrls.push(...committedMediaUrls);
       ctx.trimMessagingToolSent();
     }
   }
diff --git a/src/agents/pi-embedded-subscribe.handlers.types.ts b/src/agents/pi-embedded-subscribe.handlers.types.ts
index 9fc20f0079..435325601d 100644
--- a/src/agents/pi-embedded-subscribe.handlers.types.ts
+++ b/src/agents/pi-embedded-subscribe.handlers.types.ts
@@ -74,7 +74,7 @@ export type EmbeddedPiSubscribeState = {
   pendingMessagingTexts: Map<string, string>;
   pendingMessagingTargets: Map<string, MessagingToolSend>;
   successfulCronAdds: number;
-  pendingMessagingMediaUrls: Map<string, string>;
+  pendingMessagingMediaUrls: Map<string, string[]>;
   lastAssistant?: AgentMessage;
 };
 
diff --git a/src/plugins/wired-hooks-after-tool-call.e2e.test.ts b/src/plugins/wired-hooks-after-tool-call.e2e.test.ts
index 868f539ecd..47c6a8c262 100644
--- a/src/plugins/wired-hooks-after-tool-call.e2e.test.ts
+++ b/src/plugins/wired-hooks-after-tool-call.e2e.test.ts
@@ -41,7 +41,7 @@ function createToolHandlerCtx(params: {
       lastToolError: undefined,
       pendingMessagingTexts: new Map<string, string>(),
       pendingMessagingTargets: new Map<string, unknown>(),
-      pendingMessagingMediaUrls: new Map<string, string>(),
+      pendingMessagingMediaUrls: new Map<string, string[]>(),
       messagingToolSentTexts: [] as string[],
       messagingToolSentTextsNormalized: [] as string[],
       messagingToolSentMediaUrls: [] as string[],