diff --git a/CHANGELOG.md b/CHANGELOG.md
index 3c9e7b3e9..17c9080de 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -24,6 +24,7 @@
 - Telegram: stop typing after tool results. Thanks @AbhisekBasu1 for PR #322.
 - Messages: stop defaulting ack reactions to 👀 when identity emoji is missing.
 - Auto-reply: require slash for control commands to avoid false triggers in normal text.
+- Auto-reply: flag error payloads and improve Bun socket error messaging. Thanks @emanuelst for PR #331.
 - Commands: unify native + text chat commands behind `commands.*` config (Discord/Slack/Telegram). Thanks @thewilloftheshadow for PR #275.
 - Auto-reply: treat steer during compaction as a follow-up, queued until compaction completes.
 - Auth: lock auth profile refreshes to avoid multi-instance OAuth logouts; keep credentials on refresh failure.
diff --git a/src/auto-reply/reply/agent-runner.heartbeat-typing.test.ts b/src/auto-reply/reply/agent-runner.heartbeat-typing.test.ts
index 85eb5cf84..017a51ca9 100644
--- a/src/auto-reply/reply/agent-runner.heartbeat-typing.test.ts
+++ b/src/auto-reply/reply/agent-runner.heartbeat-typing.test.ts
@@ -209,4 +209,26 @@ describe("runReplyAgent typing (heartbeat)", () => {
     expect(payloads[0]?.text).toContain("count 1");
     expect(sessionStore.main.compactionCount).toBe(1);
   });
+
+  it("rewrites Bun socket errors into friendly text", async () => {
+    runEmbeddedPiAgentMock.mockImplementationOnce(async () => ({
+      payloads: [
+        {
+          text: "TypeError: The socket connection was closed unexpectedly. For more information, pass `verbose: true` in the second argument to fetch()",
+          isError: true,
+        },
+      ],
+      meta: {},
+    }));
+
+    const { run } = createMinimalRun();
+    const res = await run();
+    const payloads = Array.isArray(res) ? res : res ? [res] : [];
+    expect(payloads.length).toBe(1);
+    expect(payloads[0]?.text).toContain("LLM connection failed");
+    expect(payloads[0]?.text).toContain(
+      "socket connection was closed unexpectedly",
+    );
+    expect(payloads[0]?.text).toContain("```");
+  });
 });
diff --git a/src/auto-reply/reply/agent-runner.ts b/src/auto-reply/reply/agent-runner.ts
index d25aac8e6..79b85e57a 100644
--- a/src/auto-reply/reply/agent-runner.ts
+++ b/src/auto-reply/reply/agent-runner.ts
@@ -31,6 +31,21 @@ import { extractReplyToTag } from "./reply-tags.js";
 import { incrementCompactionCount } from "./session-updates.js";
 import type { TypingController } from "./typing.js";
 
+const BUN_FETCH_SOCKET_ERROR_RE = /socket connection was closed unexpectedly/i;
+
+const isBunFetchSocketError = (message?: string) =>
+  Boolean(message && BUN_FETCH_SOCKET_ERROR_RE.test(message));
+
+const formatBunFetchSocketError = (message: string) => {
+  const trimmed = message.trim();
+  return [
+    "⚠️ LLM connection failed. This could be due to server issues, network problems, or context length exceeded (e.g., with local LLMs like LM Studio). Original error:",
+    "```",
+    trimmed || "Unknown error",
+    "```",
+  ].join("\n");
+};
+
 export async function runReplyAgent(params: {
   commandBody: string;
   followupRun: FollowupRun;
@@ -403,19 +418,8 @@ export async function runReplyAgent(params: {
       : payloadArray.flatMap((payload) => {
           let text = payload.text;
 
-          if (payload.isError) {
-            // Handle Bun fetch socket connection error that may indicate a context length issue
-            // Error source: https://github.com/oven-sh/bun/blob/main/src/bun.js/webcore/fetch/FetchTasklet.zig
-            const isBunFetchSocketError =
-              text ===
-              "The socket connection was closed unexpectedly. For more information, pass `verbose: true` in the second argument to fetch()";
-
-            if (isBunFetchSocketError) {
-              text = `⚠️ LLM connection failed. This could be due to server issues, network problems, or context length exceeded (e.g., with local LLMs like LM Studio). Original error:
-              \`\`\`
-              ${text || "Unknown error"}
-              \`\`\``;
-            }
+          if (payload.isError && text && isBunFetchSocketError(text)) {
+            text = formatBunFetchSocketError(text);
           }
 
           if (!text || !text.includes("HEARTBEAT_OK"))
diff --git a/src/auto-reply/types.ts b/src/auto-reply/types.ts
index 62b6d75bb..b76a0a5a1 100644
--- a/src/auto-reply/types.ts
+++ b/src/auto-reply/types.ts
@@ -14,4 +14,5 @@ export type ReplyPayload = {
   mediaUrl?: string;
   mediaUrls?: string[];
   replyToId?: string;
+  isError?: boolean;
 };