diff --git a/CHANGELOG.md b/CHANGELOG.md
index 4de6bcb0e..717b268cb 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -4,6 +4,7 @@
 
 - Discord: stop provider when gateway reconnects are exhausted and surface errors. (#514) — thanks @joshp123
 - Auto-reply: preserve block reply ordering with timeout fallback for streaming. (#503) — thanks @joshp123
+- Auto-reply: avoid splitting outbound chunks inside parentheses. (#499) — thanks @philipp-spiess
 - Status: show provider prefix in /status model display. (#506) — thanks @mcinteerj
 - macOS: package ClawdbotKit resources and Swift 6.2 compatibility dylib to avoid launch/tool crashes. (#473) — thanks @gupsammy
 - WhatsApp: group `/model list` output by provider for scannability. (#456) - thanks @mcinteerj
diff --git a/src/auto-reply/chunk.test.ts b/src/auto-reply/chunk.test.ts
index c385d270d..335576b3c 100644
--- a/src/auto-reply/chunk.test.ts
+++ b/src/auto-reply/chunk.test.ts
@@ -67,6 +67,12 @@ describe("chunkText", () => {
     const chunks = chunkText(text, 10);
     expect(chunks).toEqual(["Supercalif", "ragilistic", "expialidoc", "ious"]);
   });
+
+  it("keeps parenthetical phrases together", () => {
+    const text = "Heads up now (Though now I'm curious)ok";
+    const chunks = chunkText(text, 35);
+    expect(chunks).toEqual(["Heads up now", "(Though now I'm curious)ok"]);
+  });
 });
 
 describe("resolveTextChunkLimit", () => {