diff --git a/extensions/imessage/src/send.test.ts b/extensions/imessage/src/send.test.ts
index 7a163a2ac33..b2ef938ae59 100644
--- a/extensions/imessage/src/send.test.ts
+++ b/extensions/imessage/src/send.test.ts
@@ -200,6 +200,42 @@ describe("sendMessageIMessage receipts", () => {
     expect(client["request"]).not.toHaveBeenCalled();
   });
 
+  it("preserves audioAsVoice media when replying to an iMessage thread", async () => {
+    const client = createClient({ message_id: 12345 });
+    const runCliJson = vi.fn().mockResolvedValueOnce({ messageId: "p:0/threaded-voice-guid" });
+
+    const result = await sendMessageIMessage("chat_guid:chat-1", "", {
+      config: IMESSAGE_TEST_CFG,
+      client,
+      mediaUrl: "/tmp/voice.caf",
+      audioAsVoice: true,
+      replyToId: "p:0/reply-guid",
+      resolveAttachmentImpl: async () => ({ path: "/tmp/voice.caf", contentType: "audio/x-caf" }),
+      runCliJson,
+    });
+
+    expect(result.messageId).toBe("p:0/threaded-voice-guid");
+    expect(runCliJson.mock.calls).toEqual([
+      [
+        [
+          "send-attachment",
+          "--chat",
+          "chat-1",
+          "--file",
+          "/tmp/voice.caf",
+          "--audio",
+          "--reply-to",
+          "p:0/reply-guid",
+          "--transport",
+          "auto",
+        ],
+      ],
+    ]);
+    expect(result.receipt.replyToId).toBe("p:0/reply-guid");
+    expect(result.receipt.parts.map((part) => part.kind)).toEqual(["voice"]);
+    expect(client["request"]).not.toHaveBeenCalled();
+  });
+
   it("resolves chat_id media-only payloads before using send-attachment", async () => {
     const client = createClient({ message_id: 12345 });
     const runCliJson = vi
diff --git a/extensions/imessage/src/send.ts b/extensions/imessage/src/send.ts
index 95b73c91d0c..83f6d974b64 100644
--- a/extensions/imessage/src/send.ts
+++ b/extensions/imessage/src/send.ts
@@ -731,6 +731,7 @@ async function trySendAttachmentForTarget(params: {
   service?: IMessageService;
   filePath: string;
   audioAsVoice?: boolean;
+  replyToId?: string;
   echoText?: string;
   runCliJson: (args: readonly string[]) => Promise<Record<string, unknown>>;
   resolveMessageGuidImpl?: IMessageSendOpts["resolveMessageGuidImpl"];
@@ -761,6 +762,7 @@ async function trySendAttachmentForTarget(params: {
       "--file",
       params.filePath,
       ...(params.audioAsVoice ? ["--audio"] : []),
+      ...(params.replyToId ? ["--reply-to", params.replyToId] : []),
       "--transport",
       "auto",
     ]);
@@ -826,6 +828,7 @@ async function trySendAttachmentForTarget(params: {
       messageId,
       target: params.target,
       kind: params.audioAsVoice ? "voice" : "media",
+      ...(params.replyToId ? { replyToId: params.replyToId } : {}),
     }),
   };
 }
@@ -908,7 +911,7 @@ export async function sendMessageIMessage(
     opts.runCliJson ??
     ((args: readonly string[]) => runIMessageCliJson(cliPath, dbPath, args, timeoutMs));
 
-  if (filePath && !resolvedReplyToId) {
+  if (filePath && (!resolvedReplyToId || opts.audioAsVoice)) {
     const attachmentEchoText = message.trim()
       ? resolveOutboundEchoText("", mediaContentType)
       : echoText;
@@ -919,6 +922,7 @@ export async function sendMessageIMessage(
       service,
       filePath,
       audioAsVoice: opts.audioAsVoice,
+      ...(resolvedReplyToId ? { replyToId: resolvedReplyToId } : {}),
       echoText: attachmentEchoText,
       runCliJson,
       resolveMessageGuidImpl: opts.resolveMessageGuidImpl,