--- /SHiREVault/Backup/OSBackups/SHIRE-ACADEMY-ROUND3-TIMEOUT-CONTRACT-REPAIR-20260805T123006Z/before/design_academy_round3_timeout_selftest.py	2026-08-05 20:30:05.995778000 +0800
+++ /SHiREVault/Backup/OSBackups/SHIRE-ACADEMY-ROUND3-TIMEOUT-CONTRACT-REPAIR-20260805T123006Z/staged/design_academy_round3_timeout_selftest.py	2026-08-05 20:30:07.472489500 +0800
@@ -5,10 +5,20 @@
 import hashlib
 import json
 import socket
+import sys
 import urllib.error
 from pathlib import Path
 
 ROOT = Path(__file__).resolve().parent.parent
+
+if str(ROOT) not in sys.path:
+    sys.path.insert(0, str(ROOT))
+
+from services.design_academy_practice_service import (
+    AcademyBrainResponseError,
+    practice_service,
+)
+
 BRAIN = ROOT / "ai" / "brain_server.py"
 SERVICE = ROOT / "services" / "design_academy_practice_service.py"
 
@@ -94,6 +104,39 @@
 assert service_ns["_academy_client_timeout_for_round"](2) == 300
 assert service_ns["_academy_client_timeout_for_round"](3) == 420
 
+timeout_failure = AcademyBrainResponseError(
+    "Brain API HTTP 504: Academy model request timed out",
+    {
+        "retryable": True,
+        "infrastructure_failure": True,
+        "timeout_stage": "ollama_generation",
+    },
+)
+
+assert (
+    practice_service._transient_brain_failure(
+        timeout_failure
+    )
+    is True
+)
+
+contract_failure = AcademyBrainResponseError(
+    "Brain API HTTP 422: Academy structured output invalid",
+    {
+        "retryable": False,
+        "infrastructure_failure": False,
+        "content_format_failure": True,
+        "failure_class": "academy_output_contract_failure",
+    },
+)
+
+assert (
+    practice_service._transient_brain_failure(
+        contract_failure
+    )
+    is False
+)
+
 required_brain_tokens = [
     'ACADEMY_OUTPUT_CONTRACT = "academy_round_json_v6"',
     'os.environ.get("SHIRE_ACADEMY_ROUND3_TIMEOUT", "360")',
@@ -110,7 +153,9 @@
     'ACADEMY_ROUND3_CLIENT_TIMEOUT = 420',
     'timeout=_academy_client_timeout_for_round(round_number)',
     '"practice_round3_client_timeout_seconds": ACADEMY_ROUND3_CLIENT_TIMEOUT',
-    '"http 504"',
+    'payload.get("infrastructure_failure") is True',
+    'return payload.get("retryable") is True',
+    '"brain api practice request failed"',
     'if payload.get("output_contract") != "academy_round_json_v6"',
     'if payload.get("context_profile") != "academy_round_specific_v5"',
 ]
@@ -138,6 +183,8 @@
     "structured_timeout_http_status": 504,
     "structured_timeout_retryable": True,
     "structured_timeout_infrastructure_failure": True,
+    "structured_timeout_classifier_verified": True,
+    "contract_failure_not_classified_as_timeout": True,
     "empty_raw_answer_sha256_audited": True,
     "round3_schema_preserved": True,
     "round2_completeness_guard_preserved": True,