From 7f4f322c7385049dcc1c12e06faad0a1632c28c4 Mon Sep 17 00:00:00 2001
From: roboomp <omp@can.ac>
Date: Mon, 27 Jul 2026 18:19:38 +0000
Subject: [PATCH] fix(cli): wrap streaming-phase download timeout with friendly
 message

downloadVerifiedBinary only wrapped isTimeoutError around the fetch()
catch, so a 15-minute timeout firing while pipeline() streamed the
response body re-threw the raw "TimeoutError: The operation timed out."
Mirror the wrap into the pipeline catch after cleaning up the partial
file, matching the connection-phase message.

Fixes #6822
---
 packages/coding-agent/CHANGELOG.md            |  4 +++
 packages/coding-agent/src/cli/update-cli.ts   |  3 +++
 packages/coding-agent/test/update-cli.test.ts | 25 +++++++++++++++++++
 3 files changed, 32 insertions(+)

diff --git a/packages/coding-agent/CHANGELOG.md b/packages/coding-agent/CHANGELOG.md
index 280be8c1e..24402acf5 100644
--- a/packages/coding-agent/CHANGELOG.md
+++ b/packages/coding-agent/CHANGELOG.md
@@ -2,6 +2,10 @@
 
 ## [Unreleased]
 
+### Fixed
+
+- Fixed `omp update` surfacing a raw `TimeoutError: The operation timed out.` when the 15-minute download deadline fired while streaming the binary body rather than during the initial `fetch()`. The streaming-phase catch now emits the same friendly `Timed out downloading release binary after 15 minutes` message as the connection phase ([#6822](https://github.com/can1357/oh-my-pi/issues/6822)).
+
 ## [17.1.6] - 2026-07-27
 
 ### Added
diff --git a/packages/coding-agent/src/cli/update-cli.ts b/packages/coding-agent/src/cli/update-cli.ts
index e86d22782..3b87fc6b0 100644
--- a/packages/coding-agent/src/cli/update-cli.ts
+++ b/packages/coding-agent/src/cli/update-cli.ts
@@ -231,6 +231,9 @@ export async function downloadVerifiedBinary(options: VerifiedBinaryDownloadOpti
 		await fs.promises.chmod(options.targetPath, 0o755);
 	} catch (err) {
 		await unlinkIfExists(options.targetPath);
+		if (isTimeoutError(err)) {
+			throw new Error("Timed out downloading release binary after 15 minutes", { cause: err });
+		}
 		throw err;
 	}
 }
diff --git a/packages/coding-agent/test/update-cli.test.ts b/packages/coding-agent/test/update-cli.test.ts
index 88df3a3fb..c232253c4 100644
--- a/packages/coding-agent/test/update-cli.test.ts
+++ b/packages/coding-agent/test/update-cli.test.ts
@@ -465,6 +465,31 @@ describe("update-cli release binary integrity", () => {
 		expect(await Bun.file(targetPath).exists()).toBe(false);
 	});
 
+	it("wraps a timeout during body streaming with a friendly message", async () => {
+		const dir = await makeTempDir();
+		const targetPath = path.join(dir, binaryName);
+		const body = new ReadableStream<Uint8Array>(
+			{
+				pull(controller) {
+					controller.enqueue(new Uint8Array(1));
+					controller.error(new DOMException("The operation timed out.", "TimeoutError"));
+				},
+			},
+			{ highWaterMark: 0 },
+		);
+
+		await expect(
+			downloadVerifiedBinary({
+				url,
+				targetPath,
+				expectedSize: Buffer.byteLength(content),
+				expectedDigest: digest,
+				fetchImpl: async () => new Response(body),
+			}),
+		).rejects.toThrow("Timed out downloading release binary after 15 minutes");
+		expect(await Bun.file(targetPath).exists()).toBe(false);
+	});
+
 	it("removes downloads whose size or digest does not match", async () => {
 		const dir = await makeTempDir();
 		const targetPath = path.join(dir, binaryName);