From 46be5eac7d53b4b7826c59a744ba01d0b885ab10 Mon Sep 17 00:00:00 2001
From: Peter Steinberger <steipete@gmail.com>
Date: Tue, 25 Nov 2025 17:52:57 +0100
Subject: [PATCH] Auto-reply: send timeout fallback and tests

---
 CHANGELOG.md            |  3 ++-
 src/auto-reply/reply.ts |  8 ++++++
 src/index.core.test.ts  | 60 +++++++++++++++++++++++++++++++++++++++++
 3 files changed, 70 insertions(+), 1 deletion(-)

diff --git a/CHANGELOG.md b/CHANGELOG.md
index 5ba971847..d67c62382 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -3,7 +3,8 @@
 ## [Unreleased] 0.1.4
 
 ### Pending
-- (add entries here)
+- Auto-replies now send a WhatsApp fallback message when a command/Claude run hits the timeout, including up to 800 chars of partial stdout so the user still sees progress.
+- Added tests covering the new timeout fallback behavior and partial-output truncation.
 
 ## 0.1.3 — 2025-11-25
 
diff --git a/src/auto-reply/reply.ts b/src/auto-reply/reply.ts
index e6178a603..518b95eb4 100644
--- a/src/auto-reply/reply.ts
+++ b/src/auto-reply/reply.ts
@@ -386,6 +386,14 @@ export async function getReplyFromConfig(
 				console.error(
 					`Command auto-reply timed out after ${elapsed}ms (limit ${timeoutMs}ms)`,
 				);
+				const baseMsg = `Command timed out after ${timeoutSeconds}s. Try a shorter prompt or split the request.`;
+				const partial = errorObj.stdout?.trim();
+				const partialSnippet =
+					partial && partial.length > 800 ? `${partial.slice(0, 800)}...` : partial;
+				const text = partialSnippet
+					? `${baseMsg}\n\nPartial output before timeout:\n${partialSnippet}`
+					: baseMsg;
+				return { text };
 			} else {
 				logError(
 					`Command auto-reply failed after ${elapsed}ms: ${String(err)}`,
diff --git a/src/index.core.test.ts b/src/index.core.test.ts
index 820cedb22..1e134cf5d 100644
--- a/src/index.core.test.ts
+++ b/src/index.core.test.ts
@@ -300,6 +300,66 @@ describe("config and templating", () => {
 		expect(result?.mediaUrl).toBeUndefined();
 	});
 
+	it("returns timeout reply with partial stdout snippet", async () => {
+		const partial = "x".repeat(900);
+		const runSpy = vi.fn().mockRejectedValue({
+			killed: true,
+			signal: "SIGKILL",
+			stdout: partial,
+			stderr: "",
+		});
+		const cfg = {
+			inbound: {
+				reply: {
+					mode: "command" as const,
+					command: ["echo", "{{Body}}"],
+					timeoutSeconds: 42,
+				},
+			},
+		};
+
+		const result = await index.getReplyFromConfig(
+			{ Body: "hi", From: "+1", To: "+2" },
+			undefined,
+			cfg,
+			runSpy,
+		);
+
+		expect(result?.text).toContain("Command timed out after 42s");
+		expect(result?.text).toContain("Partial output before timeout");
+		expect(result?.text).toContain(`${partial.slice(0, 800)}...`);
+		expect(result?.text).not.toContain(partial);
+	});
+
+	it("returns timeout reply without partial output when none is available", async () => {
+		const runSpy = vi.fn().mockRejectedValue({
+			killed: true,
+			signal: "SIGKILL",
+			stdout: "",
+			stderr: "",
+		});
+		const cfg = {
+			inbound: {
+				reply: {
+					mode: "command" as const,
+					command: ["echo", "{{Body}}"],
+					timeoutSeconds: 5,
+				},
+			},
+		};
+
+		const result = await index.getReplyFromConfig(
+			{ Body: "hi", From: "+1", To: "+2" },
+			undefined,
+			cfg,
+			runSpy,
+		);
+
+		expect(result?.text).toBe(
+			"Command timed out after 5s. Try a shorter prompt or split the request.",
+		);
+	});
+
 	it("splitMediaFromOutput strips media token and preserves text", () => {
 		const { text, mediaUrl } = splitMediaFromOutput(
 			"line1\nMEDIA:https://x/y.png\nline2",