diff --git a/CHANGELOG.md b/CHANGELOG.md
index ed9e17b43..7d4adc782 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -70,6 +70,7 @@
 - Discord: include recent guild context when replying to mentions and add `discord.historyLimit` to tune how many messages are captured.
 - Discord: include author tag + id in group context `[from:]` lines for ping-ready replies (thanks @thewilloftheshadow).
 - Discord: include replied-to message context when a Discord message references another message (thanks @thewilloftheshadow).
+- Discord: preserve newlines when stripping reply tags from agent output.
 - Gateway: fix TypeScript build by aligning hook mapping `channel` types and removing a dead Group DM branch in Discord monitor.
 - Skills: switch imsg installer to brew tap formula.
 - Skills: gate macOS-only skills by OS and surface block reasons in the Skills UI.
diff --git a/src/auto-reply/reply.directive.test.ts b/src/auto-reply/reply.directive.test.ts
index 709a2fa8c..aac22e6b2 100644
--- a/src/auto-reply/reply.directive.test.ts
+++ b/src/auto-reply/reply.directive.test.ts
@@ -109,6 +109,15 @@ describe("directive parsing", () => {
     expect(res.cleaned).toBe("see now");
   });
 
+  it("preserves newlines when stripping reply tags", () => {
+    const res = extractReplyToTag(
+      "line 1\nline 2 [[reply_to_current]]\n\nline 3",
+      "msg-2",
+    );
+    expect(res.replyToId).toBe("msg-2");
+    expect(res.cleaned).toBe("line 1\nline 2\n\nline 3");
+  });
+
   it("strips reply tags and maps reply_to_current to MessageSid", async () => {
     await withTempHome(async (home) => {
       vi.mocked(runEmbeddedPiAgent).mockResolvedValue({
diff --git a/src/auto-reply/reply.ts b/src/auto-reply/reply.ts
index 87f5d6c69..20dd24d9a 100644
--- a/src/auto-reply/reply.ts
+++ b/src/auto-reply/reply.ts
@@ -193,7 +193,10 @@ export function extractReplyToTag(
     hasTag = true;
   }
 
-  cleaned = cleaned.replace(/\s+/g, " ").trim();
+  cleaned = cleaned
+    .replace(/[ \t]+/g, " ")
+    .replace(/[ \t]*\n[ \t]*/g, "\n")
+    .trim();
   return { cleaned, replyToId, hasTag };
 }