diff --git a/apps/server/src/cloud/ManagedEndpointRuntime.test.ts b/apps/server/src/cloud/ManagedEndpointRuntime.test.ts
index d1f95140fa0a6..9dd7ac7087958 100644
--- a/apps/server/src/cloud/ManagedEndpointRuntime.test.ts
+++ b/apps/server/src/cloud/ManagedEndpointRuntime.test.ts
@@ -178,6 +178,21 @@ describe("CloudManagedEndpointRuntime", () => {
     expect(
       ManagedEndpointRuntime.classifyRelayClientOutput("2026-06-17T02:00:00Z PNC runtime panic"),
     ).toBe("warning");
+    for (const prefix of ["", "Request failed "]) {
+      expect(
+        ManagedEndpointRuntime.classifyRelayClientOutput(
+          `2026-06-17T02:00:00Z ERR ${prefix}error="Incoming request ended abruptly: context canceled" connIndex=0`,
+        ),
+      ).toBe("debug");
+    }
+    for (const line of [
+      '2026-06-17T02:00:00Z ERR error="Incoming request ended abruptly: context deadline exceeded" connIndex=0',
+      '2026-06-17T02:00:00Z ERR Failed to serve tunnel connection error="context canceled"',
+      '2026-06-17T02:00:00Z FTL error="Incoming request ended abruptly: context canceled"',
+      '2026-06-17T02:00:00Z PNC error="Incoming request ended abruptly: context canceled"',
+    ]) {
+      expect(ManagedEndpointRuntime.classifyRelayClientOutput(line)).toBe("warning");
+    }
   });
 
   it("classifies connection unregistration apart from registration and routine output", () => {
diff --git a/apps/server/src/cloud/ManagedEndpointRuntime.ts b/apps/server/src/cloud/ManagedEndpointRuntime.ts
index 66ef48f547730..34c5bb2f678fc 100644
--- a/apps/server/src/cloud/ManagedEndpointRuntime.ts
+++ b/apps/server/src/cloud/ManagedEndpointRuntime.ts
@@ -158,6 +158,13 @@ export function classifyRelayClientOutput(
   if (/\bRegistered tunnel connection\b/iu.test(line)) {
     return "connected";
   }
+  if (
+    /\bERR\s+(?:Request failed\s+)?error="Incoming request ended abruptly: context canceled"(?:\s|$)/u.test(
+      line,
+    )
+  ) {
+    return "debug";
+  }
   // cloudflared uses zerolog FTL/PNC for fatal/panic; classify them above debug too.
   if (/\b(?:ERR|WRN|FTL|PNC)\b/u.test(line)) {
     return "warning";