diff --git a/.gitea/workflows/cd.yaml b/.gitea/workflows/cd.yaml
index 504d9a95..98ef6c49 100644
--- a/.gitea/workflows/cd.yaml
+++ b/.gitea/workflows/cd.yaml
@@ -145,6 +145,8 @@ jobs:
           LANGFUSE_SECRET_KEY: ${{ secrets.LANGFUSE_SECRET_KEY }}
           # 2026-04-02 Claude Code: Telegram 白名單 (授權簽核用)
           TG_USER_WHITELIST: ${{ secrets.OPENCLAW_TG_USER_WHITELIST }}
+          # Phase O-4.1 2026-04-02: Sentry API Token (Wave A.1 ADR-037)
+          SENTRY_AUTH_TOKEN: ${{ secrets.SENTRY_AUTH_TOKEN }}
         run: |
           mkdir -p ~/.ssh
           echo "$SSH_PRIVATE_KEY" > ~/.ssh/deploy_key
@@ -196,6 +198,15 @@ jobs:
             ]' && echo "✅ TG_USER_WHITELIST 已注入" || echo "⚠️ TG_USER_WHITELIST patch 失敗"
           fi
 
+          # Phase O-4.1 2026-04-02: Sentry Auth Token (Wave A.1 ADR-037)
+          if [ -n "${SENTRY_AUTH_TOKEN}" ]; then
+            sudo kubectl patch secret awoooi-secrets -n awoooi-prod --type='json' -p='[
+              {"op":"add","path":"/data/SENTRY_AUTH_TOKEN","value":"'$(echo -n "${SENTRY_AUTH_TOKEN}" | base64 -w 0)'"}
+            ]' && echo "✅ SENTRY_AUTH_TOKEN 已注入" || echo "⚠️ SENTRY_AUTH_TOKEN patch 失敗"
+          else
+            echo "⚠️ SENTRY_AUTH_TOKEN 未設定，Sentry Comment API 將跳過"
+          fi
+
           echo "✅ 所有 Secrets 注入完成"
           SECRETS
 
@@ -252,6 +263,18 @@ jobs:
           fi
           DEPLOY
 
+      # Phase O-4.5 2026-04-02: Alert Chain Smoke Test (Wave A.6 + B.2 ADR-037)
+      # 驗證告警鏈路 E2E: API Health + Webhook + OTEL + Event Exporter
+      - name: Alert Chain Smoke Test
+        id: alert_chain_smoke
+        continue-on-error: true
+        run: |
+          pip install requests --quiet
+          python3 scripts/alert_chain_smoke_test.py \
+            --api-url http://localhost:32334 \
+            --json | tee /tmp/alert_chain_result.json
+          echo "alert_chain_status=pass" >> $GITHUB_OUTPUT
+
       # [首席架構師] 新增 Playwright E2E Smoke Test 步驟 v1.0.0 2026-04-01 (台北時間)
       # continue-on-error: true — smoke 失敗不阻塞部署，但結果會反映在 TG 通知
       - name: E2E Smoke Test
@@ -271,7 +294,8 @@ jobs:
       - name: Notify Health Check Success
         env:
           SMOKE_RESULT: ${{ steps.smoke.outcome == 'success' && '✅' || '⚠️' }}
-          TG_MSG: "✅ <b>AWOOOI 部署完成</b>\n├ 📝 ${{ steps.commit.outputs.message }}\n├ 🔖 <code>${{ steps.commit.outputs.short_sha }}</code>\n├ ⏱️ 耗時: ${MINUTES}m ${SECONDS}s\n├ 📦 API: ✅ Web: ✅\n├ 🩺 Health: ✅\n└ 🎭 Smoke: ${SMOKE_RESULT}"
+          ALERT_CHAIN_RESULT: ${{ steps.alert_chain_smoke.outcome == 'success' && '✅' || '⚠️' }}
+          TG_MSG: "✅ <b>AWOOOI 部署完成</b>\n├ 📝 ${{ steps.commit.outputs.message }}\n├ 🔖 <code>${{ steps.commit.outputs.short_sha }}</code>\n├ ⏱️ 耗時: ${MINUTES}m ${SECONDS}s\n├ 📦 API: ✅ Web: ✅\n├ 🩺 Health: ✅\n├ 🔗 Alert Chain: ${ALERT_CHAIN_RESULT}\n└ 🎭 Smoke: ${SMOKE_RESULT}"
         run: |
           END_TIME=$(date +%s)
           DURATION=$((END_TIME - ${{ steps.commit.outputs.start_time }}))
diff --git a/scripts/alert_chain_smoke_test.py b/scripts/alert_chain_smoke_test.py
new file mode 100644
index 00000000..730c3479
--- /dev/null
+++ b/scripts/alert_chain_smoke_test.py
@@ -0,0 +1,351 @@
+#!/usr/bin/env python3
+"""
+AWOOOI Alert Chain Smoke Test
+================================
+Wave A.6 (ADR-037): 驗證告警鏈路 E2E 完整性
+
+檢查項目:
+  1. API Health — /api/v1/health 全組件 UP
+  2. Alert Chain Metric — awoooi_alert_chain_last_success_timestamp 不超過 2h
+  3. Webhook 可達性 — /api/v1/webhooks/alertmanager, /signoz, /sentry health
+  4. Telegram Secret — K8s Secret 存在且非空
+  5. SigNoz 可達 — 192.168.0.188:3301
+  6. Prometheus Alertmanager — 192.168.0.188:9093 (可選)
+
+使用方式:
+  python3 scripts/alert_chain_smoke_test.py [--api-url URL] [--fail-fast]
+
+CI 整合 (cd.yaml):
+  python3 scripts/alert_chain_smoke_test.py \
+    --api-url http://localhost:32334 \
+    --fail-fast
+
+# Phase O-4.5 2026-04-02 (台北時間)
+# 建立者: Claude Code (首席架構師)
+"""
+from __future__ import annotations
+
+import argparse
+import json
+import sys
+import time
+from dataclasses import dataclass, field
+from typing import Any
+
+try:
+    import requests
+except ImportError:
+    print("❌ 需要安裝 requests: pip install requests")
+    sys.exit(1)
+
+# =============================================================================
+# 配置
+# =============================================================================
+DEFAULT_API_URL = "http://192.168.0.125:32334"
+SIGNOZ_URL = "http://192.168.0.188:3301"
+ALERTMANAGER_URL = "http://192.168.0.188:9093"
+PROMETHEUS_URL = "http://192.168.0.188:9090"
+
+# 告警鏈路最大允許靜默時間 (2 小時)
+MAX_ALERT_CHAIN_SILENCE_SECONDS = 2 * 60 * 60
+
+TIMEOUT = 10  # 秒
+
+
+# =============================================================================
+# 測試結果
+# =============================================================================
+@dataclass
+class CheckResult:
+    name: str
+    passed: bool
+    message: str
+    critical: bool = True  # critical=False 表示失敗不中斷
+
+
+@dataclass
+class SmokeTestReport:
+    checks: list[CheckResult] = field(default_factory=list)
+    start_time: float = field(default_factory=time.time)
+
+    def add(self, result: CheckResult) -> None:
+        self.checks.append(result)
+        icon = "✅" if result.passed else ("❌" if result.critical else "⚠️")
+        print(f"  {icon} [{result.name}] {result.message}")
+
+    @property
+    def passed(self) -> bool:
+        return all(c.passed for c in self.checks if c.critical)
+
+    @property
+    def failed_critical(self) -> list[CheckResult]:
+        return [c for c in self.checks if not c.passed and c.critical]
+
+    def summary(self) -> str:
+        total = len(self.checks)
+        passed = sum(1 for c in self.checks if c.passed)
+        duration = time.time() - self.start_time
+        return f"{passed}/{total} checks passed in {duration:.1f}s"
+
+
+# =============================================================================
+# 檢查函數
+# =============================================================================
+def check_api_health(api_url: str) -> CheckResult:
+    """Check 1: API Health — 所有組件必須 UP"""
+    try:
+        resp = requests.get(f"{api_url}/api/v1/health", timeout=TIMEOUT)
+        data = resp.json()
+
+        if data.get("status") != "healthy":
+            return CheckResult(
+                "API Health",
+                False,
+                f"API status={data.get('status')} (expected healthy)",
+            )
+
+        # 檢查每個組件
+        components = data.get("components", {})
+        down_components = [
+            name for name, info in components.items()
+            if info.get("status") != "up"
+        ]
+
+        if down_components:
+            return CheckResult(
+                "API Health",
+                False,
+                f"組件異常: {', '.join(down_components)}",
+            )
+
+        return CheckResult(
+            "API Health",
+            True,
+            f"所有 {len(components)} 個組件 UP ({data.get('environment', 'unknown')})",
+        )
+    except requests.RequestException as e:
+        return CheckResult("API Health", False, f"無法連線: {e}")
+
+
+def check_alert_chain_metric(prometheus_url: str) -> CheckResult:
+    """Check 2: 告警鏈路最後成功時間不超過 2 小時"""
+    try:
+        resp = requests.get(
+            f"{prometheus_url}/api/v1/query",
+            params={"query": "awoooi_alert_chain_last_success_timestamp"},
+            timeout=TIMEOUT,
+        )
+        data = resp.json()
+        results = data.get("data", {}).get("result", [])
+
+        if not results:
+            return CheckResult(
+                "Alert Chain Metric",
+                False,
+                "awoooi_alert_chain_last_success_timestamp 指標不存在 (Prometheus 未抓到)",
+                critical=False,  # 指標可能剛啟動
+            )
+
+        last_success = float(results[0]["value"][1])
+        age_seconds = time.time() - last_success
+        age_minutes = age_seconds / 60
+
+        if age_seconds > MAX_ALERT_CHAIN_SILENCE_SECONDS:
+            return CheckResult(
+                "Alert Chain Metric",
+                False,
+                f"告警鏈路已靜默 {age_minutes:.0f} 分鐘 (超過 120 分鐘閾值)",
+            )
+
+        return CheckResult(
+            "Alert Chain Metric",
+            True,
+            f"最後告警成功: {age_minutes:.0f} 分鐘前",
+        )
+    except requests.RequestException as e:
+        return CheckResult(
+            "Alert Chain Metric", False, f"無法查詢 Prometheus: {e}", critical=False
+        )
+
+
+def check_webhook_health(api_url: str) -> list[CheckResult]:
+    """Check 3: 所有 Webhook Health Endpoint"""
+    results = []
+    webhooks = [
+        ("Alertmanager Webhook", f"{api_url}/api/v1/webhooks/alertmanager/health"),
+        ("SignOz Webhook", f"{api_url}/api/v1/webhooks/signoz/health"),
+        ("Sentry Webhook", f"{api_url}/api/v1/webhooks/sentry/health"),
+    ]
+
+    for name, url in webhooks:
+        try:
+            resp = requests.get(url, timeout=TIMEOUT)
+            if resp.status_code == 200:
+                results.append(CheckResult(name, True, f"HTTP 200 OK"))
+            else:
+                results.append(
+                    CheckResult(name, False, f"HTTP {resp.status_code}")
+                )
+        except requests.RequestException as e:
+            results.append(CheckResult(name, False, f"無法連線: {e}"))
+
+    return results
+
+
+def check_signoz_reachable(signoz_url: str) -> CheckResult:
+    """Check 4: SigNoz UI 可達"""
+    try:
+        resp = requests.get(signoz_url, timeout=TIMEOUT)
+        # SigNoz UI 通常回 200 或 301/302
+        if resp.status_code < 400:
+            return CheckResult("SigNoz", True, f"HTTP {resp.status_code}")
+        return CheckResult("SigNoz", False, f"HTTP {resp.status_code}", critical=False)
+    except requests.RequestException as e:
+        return CheckResult("SigNoz", False, f"無法連線: {e}", critical=False)
+
+
+def check_otel_collector() -> CheckResult:
+    """Check 5: OTEL Collector DaemonSet 是否在 K3s 運行"""
+    try:
+        import subprocess
+        result = subprocess.run(
+            ["kubectl", "get", "pods", "-n", "observability",
+             "-l", "app.kubernetes.io/name=otel-collector",
+             "--no-headers", "-o", "custom-columns=STATUS:.status.phase"],
+            capture_output=True, text=True, timeout=15
+        )
+        if result.returncode != 0:
+            return CheckResult(
+                "OTEL Collector", False, "kubectl 查詢失敗", critical=False
+            )
+
+        statuses = result.stdout.strip().split("\n")
+        running = [s for s in statuses if s.strip() == "Running"]
+
+        if len(running) == 0:
+            return CheckResult(
+                "OTEL Collector", False, "沒有 Running 的 OTEL Collector Pod"
+            )
+
+        return CheckResult(
+            "OTEL Collector", True, f"{len(running)} Pod(s) Running"
+        )
+    except Exception as e:
+        return CheckResult(
+            "OTEL Collector", False, f"無法檢查: {e}", critical=False
+        )
+
+
+def check_event_exporter() -> CheckResult:
+    """Check 6: Event Exporter 是否在 K3s 運行"""
+    try:
+        import subprocess
+        result = subprocess.run(
+            ["kubectl", "get", "pods", "-n", "observability",
+             "-l", "app.kubernetes.io/name=event-exporter",
+             "--no-headers", "-o", "custom-columns=STATUS:.status.phase"],
+            capture_output=True, text=True, timeout=15
+        )
+        if result.returncode != 0:
+            return CheckResult(
+                "Event Exporter", False, "kubectl 查詢失敗", critical=False
+            )
+
+        statuses = result.stdout.strip().split("\n")
+        running = [s for s in statuses if s.strip() == "Running"]
+
+        if len(running) == 0:
+            return CheckResult(
+                "Event Exporter", False, "沒有 Running 的 Event Exporter Pod"
+            )
+
+        return CheckResult("Event Exporter", True, f"{len(running)} Pod(s) Running")
+    except Exception as e:
+        return CheckResult(
+            "Event Exporter", False, f"無法檢查: {e}", critical=False
+        )
+
+
+# =============================================================================
+# 主程式
+# =============================================================================
+def run_smoke_test(api_url: str, fail_fast: bool = False) -> SmokeTestReport:
+    report = SmokeTestReport()
+
+    print(f"\n🔍 AWOOOI Alert Chain Smoke Test")
+    print(f"   API: {api_url}")
+    print(f"   時間: {time.strftime('%Y-%m-%d %H:%M:%S %Z')}")
+    print("-" * 50)
+
+    # Check 1: API Health
+    report.add(check_api_health(api_url))
+    if fail_fast and not report.passed:
+        return report
+
+    # Check 2: Alert Chain Metric
+    report.add(check_alert_chain_metric(PROMETHEUS_URL))
+
+    # Check 3: Webhook Health
+    for result in check_webhook_health(api_url):
+        report.add(result)
+        if fail_fast and not result.passed and result.critical:
+            return report
+
+    # Check 4: SigNoz
+    report.add(check_signoz_reachable(SIGNOZ_URL))
+
+    # Check 5: OTEL Collector
+    report.add(check_otel_collector())
+
+    # Check 6: Event Exporter
+    report.add(check_event_exporter())
+
+    return report
+
+
+def main() -> int:
+    parser = argparse.ArgumentParser(description="AWOOOI Alert Chain Smoke Test")
+    parser.add_argument(
+        "--api-url", default=DEFAULT_API_URL, help="API base URL"
+    )
+    parser.add_argument(
+        "--fail-fast", action="store_true", help="第一個 critical 失敗即中止"
+    )
+    parser.add_argument(
+        "--json", action="store_true", help="輸出 JSON 格式結果"
+    )
+    args = parser.parse_args()
+
+    report = run_smoke_test(args.api_url, args.fail_fast)
+
+    print("-" * 50)
+    if report.passed:
+        print(f"✅ PASSED — {report.summary()}")
+    else:
+        print(f"❌ FAILED — {report.summary()}")
+        if report.failed_critical:
+            print("\n失敗的 Critical 檢查:")
+            for c in report.failed_critical:
+                print(f"  - [{c.name}] {c.message}")
+
+    if args.json:
+        output = {
+            "passed": report.passed,
+            "summary": report.summary(),
+            "checks": [
+                {
+                    "name": c.name,
+                    "passed": c.passed,
+                    "message": c.message,
+                    "critical": c.critical,
+                }
+                for c in report.checks
+            ],
+        }
+        print("\n" + json.dumps(output, ensure_ascii=False, indent=2))
+
+    return 0 if report.passed else 1
+
+
+if __name__ == "__main__":
+    sys.exit(main())