From 5a0369197ec58d67a94a8eb7532ab96842028787 Mon Sep 17 00:00:00 2001
From: Benedikt Schackenberg <benedikt@schackenberg.dev>
Date: Sun, 15 Mar 2026 19:16:23 +0000
Subject: [PATCH] fix: exclude HTTP 408 from permanent delivery errors

---
 src/infra/outbound/delivery-queue.test.ts | 9 +++++++++
 src/infra/outbound/delivery-queue.ts      | 2 +-
 2 files changed, 10 insertions(+), 1 deletion(-)

diff --git a/src/infra/outbound/delivery-queue.test.ts b/src/infra/outbound/delivery-queue.test.ts
index f22f82af2ef..63a7b5a9abe 100644
--- a/src/infra/outbound/delivery-queue.test.ts
+++ b/src/infra/outbound/delivery-queue.test.ts
@@ -61,4 +61,13 @@ describe("isPermanentDeliveryError", () => {
   it("returns false for timeout errors", () => {
     expect(isPermanentDeliveryError("request timed out")).toBe(false);
   });
+
+  // 408 should NOT be permanent (request timeout = transient)
+  it("does NOT treat HTTP 408 as permanent", () => {
+    expect(isPermanentDeliveryError("status 408")).toBe(false);
+  });
+
+  it("does NOT treat HTTP 408 Request Timeout as permanent", () => {
+    expect(isPermanentDeliveryError("HTTP 408 Request Timeout")).toBe(false);
+  });
 });
diff --git a/src/infra/outbound/delivery-queue.ts b/src/infra/outbound/delivery-queue.ts
index 193fe33ddcf..6af947c1ea1 100644
--- a/src/infra/outbound/delivery-queue.ts
+++ b/src/infra/outbound/delivery-queue.ts
@@ -452,7 +452,7 @@ export function isPermanentDeliveryError(error: string): boolean {
   const statusMatch = HTTP_STATUS_PATTERN.exec(error);
   if (statusMatch) {
     const status = parseInt(statusMatch[1], 10);
-    if (status >= 400 && status < 500 && status !== 429) {
+    if (status >= 400 && status < 500 && status !== 429 && status !== 408) {
       return true;
     }
   }