diff --git a/src/auto-reply/reply/reply-delivery.test.ts b/src/auto-reply/reply/reply-delivery.test.ts
index 6978292e4748..083b60a38d05 100644
--- a/src/auto-reply/reply/reply-delivery.test.ts
+++ b/src/auto-reply/reply/reply-delivery.test.ts
@@ -311,6 +311,18 @@ describe("createBlockReplyDeliveryHandler", () => {
     expect(normalized.payload.mediaUrls).toEqual(["./report.pdf"]);
   });
 
+  it("keeps parsed media when an explicit media list is empty", () => {
+    const normalized = normalizeReplyPayloadDirectives({
+      payload: { text: "MEDIA: ./report.pdf", mediaUrls: [] },
+      trimLeadingWhitespace: true,
+      parseMode: "auto",
+    });
+
+    expect(normalized.payload.text).toBeUndefined();
+    expect(normalized.payload.mediaUrl).toBe("./report.pdf");
+    expect(normalized.payload.mediaUrls).toEqual([]);
+  });
+
   it("leaves media-looking text alone when media directive parsing is disabled", () => {
     const normalized = normalizeReplyPayloadDirectives({
       payload: { text: "Result\nMEDIA: ./image.png" },
diff --git a/src/auto-reply/reply/reply-delivery.ts b/src/auto-reply/reply/reply-delivery.ts
index 3c63ee62d820..18626e65d0fe 100644
--- a/src/auto-reply/reply/reply-delivery.ts
+++ b/src/auto-reply/reply/reply-delivery.ts
@@ -49,7 +49,7 @@ export function normalizeReplyPayloadDirectives(params: {
   }
 
   const mediaUrls = params.payload.mediaUrls ?? parsed?.mediaUrls;
-  const mediaUrl = params.payload.mediaUrl ?? mediaUrls?.[0];
+  const mediaUrl = params.payload.mediaUrl ?? parsed?.mediaUrls?.[0] ?? mediaUrls?.[0];
 
   const channelData = mergeReactionDirectiveChannelData(
     params.payload.channelData,