diff --git a/apps/api/src/common/domain-exception.filter.ts b/apps/api/src/common/domain-exception.filter.ts
index 4aaa89a..d7baa90 100644
--- a/apps/api/src/common/domain-exception.filter.ts
+++ b/apps/api/src/common/domain-exception.filter.ts
@@ -4,6 +4,7 @@ import {
   Catch,
   HttpException,
   HttpStatus,
+  Logger,
   type ExceptionFilter,
 } from "@nestjs/common";
 import type { Response } from "express";
@@ -12,11 +13,28 @@ import type { RequestWithId } from "./request-id.middleware.js";
 
 @Catch()
 export class DomainExceptionFilter implements ExceptionFilter {
+  private readonly logger = new Logger(DomainExceptionFilter.name);
+
   catch(exception: unknown, host: ArgumentsHost): void {
     const http = host.switchToHttp();
     const request = http.getRequest<RequestWithId>();
     const response = http.getResponse<Response>();
     const normalized = this.normalize(exception);
+    if (
+      !(exception instanceof DomainException) &&
+      !(exception instanceof HttpException)
+    ) {
+      const exceptionType =
+        exception instanceof Error
+          ? exception.constructor.name
+          : typeof exception;
+      this.logger.error({
+        event: "Unhandled exception",
+        requestId: request.requestId,
+        code: normalized.code,
+        exceptionType,
+      });
+    }
     const body: ErrorResponse = {
       code: normalized.code,
       message: normalized.message,
diff --git a/apps/api/src/common/http-response.interceptor.ts b/apps/api/src/common/http-response.interceptor.ts
index c06e82e..d0b428f 100644
--- a/apps/api/src/common/http-response.interceptor.ts
+++ b/apps/api/src/common/http-response.interceptor.ts
@@ -9,38 +9,45 @@ import type { Observable } from "rxjs";
 import { map } from "rxjs/operators";
 import type { RequestWithId } from "./request-id.middleware.js";
 
-const SAFE_REQUEST_ID = /^[A-Za-z0-9._:-]{1,128}$/;
+const PREWRAPPED_RESPONSE = Symbol("prewrapped-response");
 
-export const isSuccessEnvelope = (
+export interface PrewrappedResponse<T> {
+  readonly [PREWRAPPED_RESPONSE]: true;
+  readonly response: SuccessResponse<T>;
+}
+
+export const prewrapped = <T>(
+  response: SuccessResponse<T>,
+): PrewrappedResponse<T> => ({
+  [PREWRAPPED_RESPONSE]: true,
+  response,
+});
+
+const isPrewrappedResponse = (
   value: unknown,
-): value is SuccessResponse<unknown> =>
+): value is PrewrappedResponse<unknown> =>
   typeof value === "object" &&
   value !== null &&
-  "code" in value &&
-  value.code === "OK" &&
-  "message" in value &&
-  value.message === "success" &&
-  "data" in value &&
-  "requestId" in value &&
-  typeof value.requestId === "string" &&
-  SAFE_REQUEST_ID.test(value.requestId);
+  PREWRAPPED_RESPONSE in value &&
+  value[PREWRAPPED_RESPONSE] === true;
 
 @Injectable()
 export class HttpResponseInterceptor<T> implements NestInterceptor<
-  T,
-  T | SuccessResponse<T>
+  T | PrewrappedResponse<T>,
+  SuccessResponse<T>
 > {
   intercept(
     context: ExecutionContext,
-    next: CallHandler<T>,
-  ): Observable<T | SuccessResponse<T>> {
+    next: CallHandler<T | PrewrappedResponse<T>>,
+  ): Observable<SuccessResponse<T>> {
     const request = context.switchToHttp().getRequest<RequestWithId>();
-    return next
-      .handle()
-      .pipe(
-        map((data) =>
-          isSuccessEnvelope(data) ? data : ok(data, request.requestId),
-        ),
-      );
+    return next.handle().pipe(
+      map((data) => {
+        if (isPrewrappedResponse(data)) {
+          return { ...data.response, requestId: request.requestId };
+        }
+        return ok(data, request.requestId);
+      }),
+    );
   }
 }
diff --git a/apps/api/src/health/health.e2e-spec.ts b/apps/api/src/health/health.e2e-spec.ts
index 656be1e..9ef4d2f 100644
--- a/apps/api/src/health/health.e2e-spec.ts
+++ b/apps/api/src/health/health.e2e-spec.ts
@@ -5,6 +5,7 @@ import {
   Controller,
   Get,
   HttpStatus,
+  Logger,
   Post,
   type INestApplication,
 } from "@nestjs/common";
@@ -12,10 +13,12 @@ import { Test } from "@nestjs/testing";
 import { ErrorCode, ok } from "@drift/contracts";
 import { Type } from "class-transformer";
 import { IsInt, IsString } from "class-validator";
+import { createServer, type Socket } from "node:net";
 import request from "supertest";
 import { afterAll, beforeAll, describe, expect, it, vi } from "vitest";
 import { AppModule } from "../app.module.js";
 import { DomainException } from "../common/domain.exception.js";
+import { prewrapped } from "../common/http-response.interceptor.js";
 import { sanitizeRequestId } from "../common/request-id.middleware.js";
 import { PrismaService } from "../database/prisma.service.js";
 import { bootstrap, configureApp } from "../main.js";
@@ -46,15 +49,16 @@ class ProbeController {
 
   @Get("envelope")
   envelope() {
-    return ok({ already: "wrapped" }, "controller-request-id");
+    return prewrapped(ok({ already: "wrapped" }, "forged-request-id"));
   }
 
   @Get("envelope-lookalike")
   envelopeLookalike() {
     return {
-      code: "BUSINESS_CODE",
+      code: "OK",
+      message: "success",
+      data: { business: true },
       requestId: "business-request-id",
-      value: 1,
     };
   }
 
@@ -171,6 +175,9 @@ describe("API infrastructure", () => {
   });
 
   it("does not leak internal errors", async () => {
+    const errorLog = vi
+      .spyOn(Logger.prototype, "error")
+      .mockImplementation(() => undefined);
     const response = await request(app.getHttpServer())
       .get("/api/v1/probe/internal-error")
       .expect(500);
@@ -181,6 +188,32 @@ describe("API infrastructure", () => {
     });
     expect(JSON.stringify(response.body)).not.toContain("postgresql://");
     expect(response.body).not.toHaveProperty("stack");
+    expect(errorLog).toHaveBeenCalledOnce();
+    const logged = JSON.stringify(errorLog.mock.calls);
+    expect(logged).toContain(response.body.requestId);
+    expect(logged).toContain("INTERNAL_ERROR");
+    expect(logged).toContain("Error");
+    expect(logged).not.toContain("sensitive");
+    expect(logged).not.toContain("postgresql://");
+    errorLog.mockRestore();
+  });
+
+  it("logs Redis client errors without leaking their original message", () => {
+    const warning = vi
+      .spyOn(Logger.prototype, "warn")
+      .mockImplementation(() => undefined);
+    const service = new HealthService({} as PrismaService);
+    service.redisClient.emit(
+      "error",
+      new Error("redis://user:token@host secret redis failure"),
+    );
+    service.redisClient.emit("error", new Error("another secret"));
+    expect(warning).toHaveBeenCalledOnce();
+    const logged = JSON.stringify(warning.mock.calls);
+    expect(logged).toContain("Redis client error");
+    expect(logged).not.toContain("token");
+    expect(logged).not.toContain("secret");
+    warning.mockRestore();
   });
 
   it("rejects non-whitelisted DTO properties in the uniform envelope", async () => {
@@ -210,8 +243,9 @@ describe("API infrastructure", () => {
       code: "OK",
       message: "success",
       data: { already: "wrapped" },
-      requestId: "controller-request-id",
+      requestId: response.headers["x-request-id"],
     });
+    expect(response.body.requestId).not.toBe("forged-request-id");
   });
 
   it("wraps a business object that merely resembles an envelope", async () => {
@@ -221,9 +255,10 @@ describe("API infrastructure", () => {
     expect(response.body.code).toBe("OK");
     expect(response.body.message).toBe("success");
     expect(response.body.data).toEqual({
-      code: "BUSINESS_CODE",
+      code: "OK",
+      message: "success",
+      data: { business: true },
       requestId: "business-request-id",
-      value: 1,
     });
   });
 
@@ -278,6 +313,99 @@ describe("API infrastructure", () => {
     }
   });
 
+  it("times out and destroys a Redis connection that never answers", async () => {
+    const sockets = new Set<Socket>();
+    const server = createServer((socket) => {
+      sockets.add(socket);
+      socket.on("close", () => sockets.delete(socket));
+    });
+    await new Promise<void>((resolve) =>
+      server.listen(0, "127.0.0.1", resolve),
+    );
+    const address = server.address();
+    if (!address || typeof address === "string")
+      throw new Error("missing port");
+    const previousUrl = process.env.REDIS_URL;
+    const previousTimeout = process.env.REDIS_PROBE_TIMEOUT_MS;
+    process.env.REDIS_URL = `redis://127.0.0.1:${address.port}`;
+    process.env.REDIS_PROBE_TIMEOUT_MS = "100";
+    const service = new HealthService({
+      $queryRaw: vi.fn().mockResolvedValue([{ value: 1 }]),
+    } as unknown as PrismaService);
+    const startedAt = Date.now();
+    try {
+      await expect(service.check()).rejects.toMatchObject({
+        code: ErrorCode.SERVICE_UNAVAILABLE,
+      });
+      expect(Date.now() - startedAt).toBeLessThan(750);
+      expect(service.redisClient.isOpen).toBe(false);
+    } finally {
+      await service.onModuleDestroy();
+      for (const socket of sockets) socket.destroy();
+      await new Promise<void>((resolve, reject) =>
+        server.close((error) => (error ? reject(error) : resolve())),
+      );
+      process.env.REDIS_URL = previousUrl;
+      process.env.REDIS_PROBE_TIMEOUT_MS = previousTimeout;
+    }
+  });
+
+  it("recreates Redis after a failed probe so a recovered dependency becomes healthy", async () => {
+    const previousUrl = process.env.REDIS_URL;
+    const previousTimeout = process.env.REDIS_PROBE_TIMEOUT_MS;
+    process.env.REDIS_URL = "redis://127.0.0.1:1";
+    process.env.REDIS_PROBE_TIMEOUT_MS = "100";
+    const warning = vi
+      .spyOn(Logger.prototype, "warn")
+      .mockImplementation(() => undefined);
+    const service = new HealthService({
+      $queryRaw: vi.fn().mockResolvedValue([{ value: 1 }]),
+    } as unknown as PrismaService);
+    const failedClient = service.redisClient;
+    try {
+      await expect(service.check()).rejects.toMatchObject({
+        code: ErrorCode.SERVICE_UNAVAILABLE,
+      });
+      expect(failedClient.isOpen).toBe(false);
+      expect(warning).toHaveBeenCalledOnce();
+
+      process.env.REDIS_URL = previousUrl ?? "redis://127.0.0.1:6379";
+      await expect(service.check()).resolves.toEqual({
+        status: "ok",
+        postgres: "up",
+        redis: "up",
+      });
+      expect(service.redisClient).not.toBe(failedClient);
+      service.redisClient.emit("error", new Error("post-recovery failure"));
+      expect(warning).toHaveBeenCalledTimes(2);
+    } finally {
+      await service.onModuleDestroy();
+      warning.mockRestore();
+      process.env.REDIS_URL = previousUrl;
+      process.env.REDIS_PROBE_TIMEOUT_MS = previousTimeout;
+    }
+  });
+
+  it("destroys Redis when graceful module shutdown exceeds its deadline", async () => {
+    const previousTimeout = process.env.REDIS_PROBE_TIMEOUT_MS;
+    process.env.REDIS_PROBE_TIMEOUT_MS = "25";
+    const service = new HealthService({} as PrismaService);
+    const destroy = vi.fn();
+    Object.defineProperty(service, "redis", {
+      value: {
+        isOpen: true,
+        quit: vi.fn(() => new Promise<void>(() => undefined)),
+        destroy,
+      },
+    });
+    try {
+      await expect(service.onModuleDestroy()).resolves.toBeUndefined();
+      expect(destroy).toHaveBeenCalledOnce();
+    } finally {
+      process.env.REDIS_PROBE_TIMEOUT_MS = previousTimeout;
+    }
+  });
+
   it("returns a sanitized 503 specifically when PostgreSQL is unavailable", async () => {
     const module = await Test.createTestingModule({ imports: [AppModule] })
       .overrideProvider(PrismaService)
diff --git a/apps/api/src/health/health.service.ts b/apps/api/src/health/health.service.ts
index 07f41a8..38945c9 100644
--- a/apps/api/src/health/health.service.ts
+++ b/apps/api/src/health/health.service.ts
@@ -1,5 +1,10 @@
-import { Inject, Injectable, type OnModuleDestroy } from "@nestjs/common";
-import { createClient, type RedisClientType } from "redis";
+import {
+  Inject,
+  Injectable,
+  Logger,
+  type OnModuleDestroy,
+} from "@nestjs/common";
+import { createClient } from "redis";
 import { PrismaService } from "../database/prisma.service.js";
 import { DomainException } from "../common/domain.exception.js";
 import { ErrorCode } from "@drift/contracts";
@@ -7,26 +12,53 @@ import { HttpStatus } from "@nestjs/common";
 
 @Injectable()
 export class HealthService implements OnModuleDestroy {
-  private readonly redis: RedisClientType;
+  private redis: ReturnType<typeof createClient>;
+  private readonly probeTimeoutMs: number;
+  private readonly logger = new Logger(HealthService.name);
+  private redisDestroyed = false;
+  private redisErrorLogged = false;
 
-  get redisClient(): RedisClientType {
+  get redisClient(): ReturnType<typeof createClient> {
     return this.redis;
   }
 
   constructor(@Inject(PrismaService) private readonly prisma: PrismaService) {
-    this.redis = createClient({
+    this.probeTimeoutMs = this.readTimeout(process.env.REDIS_PROBE_TIMEOUT_MS);
+    this.redis = this.createRedisClient();
+  }
+
+  private createRedisClient(): ReturnType<typeof createClient> {
+    const redis = createClient({
       url: process.env.REDIS_URL ?? "redis://127.0.0.1:6379",
-      socket: { connectTimeout: 500, reconnectStrategy: false },
+      socket: { connectTimeout: this.probeTimeoutMs, reconnectStrategy: false },
     });
-    this.redis.on("error", () => undefined);
+    redis.on("error", () => {
+      if (this.redisErrorLogged) return;
+      this.redisErrorLogged = true;
+      this.logger.warn({ event: "Redis client error", code: "REDIS_ERROR" });
+    });
+    return redis;
+  }
+
+  private getRedisClient(): ReturnType<typeof createClient> {
+    if (this.redisDestroyed) {
+      this.redisErrorLogged = false;
+      this.redis = this.createRedisClient();
+      this.redisDestroyed = false;
+    }
+    return this.redis;
   }
 
   async check(): Promise<{ status: "ok"; postgres: "up"; redis: "up" }> {
+    const redis = this.getRedisClient();
     try {
-      if (!this.redis.isOpen) await this.redis.connect();
-      await Promise.all([this.prisma.$queryRaw`SELECT 1`, this.redis.ping()]);
+      await this.withDeadline(async () => {
+        if (!redis.isOpen) await redis.connect();
+        await Promise.all([this.prisma.$queryRaw`SELECT 1`, redis.ping()]);
+      });
       return { status: "ok", postgres: "up", redis: "up" };
     } catch {
+      this.destroyRedis();
       throw new DomainException(
         ErrorCode.SERVICE_UNAVAILABLE,
         "Dependencies unavailable",
@@ -36,6 +68,49 @@ export class HealthService implements OnModuleDestroy {
   }
 
   async onModuleDestroy(): Promise<void> {
-    if (this.redis.isOpen) await this.redis.quit();
+    if (!this.redis.isOpen) return;
+    try {
+      await this.withDeadline(() => this.redis.quit());
+    } catch {
+      this.destroyRedis();
+    }
+  }
+
+  private readTimeout(raw: string | undefined): number {
+    const timeout = Number(raw ?? 1000);
+    return Number.isFinite(timeout) && timeout > 0 ? timeout : 1000;
+  }
+
+  private withDeadline<T>(operation: () => Promise<T>): Promise<T> {
+    return new Promise<T>((resolve, reject) => {
+      const timer = setTimeout(() => {
+        this.destroyRedis();
+        reject(new Error("Redis operation timed out"));
+      }, this.probeTimeoutMs);
+      void operation().then(
+        (value) => {
+          clearTimeout(timer);
+          resolve(value);
+        },
+        (error: unknown) => {
+          clearTimeout(timer);
+          reject(
+            error instanceof Error
+              ? error
+              : new Error("Redis operation failed"),
+          );
+        },
+      );
+    });
+  }
+
+  private destroyRedis(): void {
+    if (this.redisDestroyed) return;
+    this.redisDestroyed = true;
+    try {
+      this.redis.destroy();
+    } catch {
+      // Destruction is best-effort and must never mask readiness/shutdown errors.
+    }
   }
 }