feat: implement structured logging for server and client

Server:
- Add pino and pino-http for structured logging
- Create @Logged class decorator using Proxy pattern for automatic method logging
- Add pino redact config for sensitive data (password, token, etc.)
- Move AuthMiddleware to controllers folder (per architecture diagram)
- Add LoggingMiddleware for HTTP request logging
- Replace console.log/error with structured logger in controllers and app.ts
- Decorate all repositories and GPTAdapter with @Logged

Client:
- Add react-native-logs with namespaced loggers (apiLogger, storeLogger)
- Add request/response logging to ApiClient with duration tracking

CLAUDE.md

@@ -47,6 +47,8 @@ npm run start -w @caldav/server        # Run compiled server (port 3000)
 | | Mongoose | ODM |
 | | GPT (OpenAI) | AI/LLM for chat |
 | | JWT | Authentication |
+| | pino / pino-http | Structured logging |
+| | react-native-logs | Client-side logging |
 | Planned | iCalendar | Event export/import |
 
 ## Architecture
@@ -83,9 +85,12 @@ src/
 │   ├── EventConfirmDialog.tsx  # AI-proposed event confirmation modal
 │   └── ProposedEventCard.tsx   # Chat event proposal (uses EventCardBase + confirm/reject buttons)
 ├── Themes.tsx                  # Centralized color/theme definitions
+├── logging/
+│   ├── index.ts                # Re-exports
+│   └── logger.ts               # react-native-logs config (apiLogger, storeLogger)
 ├── services/
 │   ├── index.ts                # Re-exports all services
-│   ├── ApiClient.ts            # HTTP client (get, post, put, delete)
+│   ├── ApiClient.ts            # HTTP client with request logging (get, post, put, delete)
 │   ├── AuthService.ts          # login(), register(), logout(), refresh()
 │   ├── EventService.ts         # getAll(), getById(), getByDateRange(), create(), update(), delete()
 │   └── ChatService.ts          # sendMessage(), confirmEvent(), rejectEvent(), getConversations(), getConversation()
@@ -103,12 +108,16 @@ src/
 ```
 src/
 ├── app.ts                    # Entry point, DI setup, Express config
-├── controllers/              # Request handlers
+├── controllers/              # Request handlers + middleware (per architecture diagram)
 │   ├── AuthController.ts     # login(), register(), refresh(), logout()
 │   ├── ChatController.ts     # sendMessage(), confirmEvent(), rejectEvent(), getConversations(), getConversation()
-│   └── EventController.ts    # create(), getById(), getAll(), getByDateRange(), update(), delete()
+│   ├── EventController.ts    # create(), getById(), getAll(), getByDateRange(), update(), delete()
-├── middleware/
+│   ├── AuthMiddleware.ts     # authenticate() - JWT validation
-│   └── AuthMiddleware.ts     # authenticate() - JWT validation
+│   └── LoggingMiddleware.ts  # httpLogger - pino-http request logging
+├── logging/
+│   ├── index.ts              # Re-exports
+│   ├── logger.ts             # pino config with redact for sensitive data
+│   └── Logged.ts             # @Logged() class decorator for automatic method logging
 ├── routes/                   # API endpoint definitions
 │   ├── index.ts              # Combines all routes under /api
 │   ├── auth.routes.ts        # /api/auth/*
@@ -239,6 +248,32 @@ const Schema = new Schema<Doc, Model<Doc, {}, {}, IdVirtual>, {}, {}, IdVirtual>
 
 Repositories use `doc.toJSON() as unknown as Type` casting (required because Mongoose's TypeScript types don't reflect virtual fields in toJSON output).
 
+### Logging
+
+Structured logging with pino (server) and react-native-logs (client).
+
+**Server Logging:**
+- `pino` with `pino-pretty` for development, JSON in production
+- `pino-http` middleware logs all HTTP requests (method, path, status, duration)
+- `@Logged()` class decorator for automatic method logging on repositories and services
+- Sensitive data (password, token, etc.) automatically redacted via pino's `redact` config
+
+**@Logged Decorator Pattern:**
+```typescript
+@Logged("MongoEventRepository")
+export class MongoEventRepository implements EventRepository { ... }
+
+@Logged("GPTAdapter")
+export class GPTAdapter implements AIProvider { ... }
+```
+
+The decorator uses a Proxy to intercept method calls lazily, preserves sync/async nature, and logs start/completion/failure with duration.
+
+**Client Logging:**
+- `react-native-logs` with namespaced loggers (apiLogger, storeLogger)
+- ApiClient logs all requests with method, endpoint, status, duration
+- Log level: debug in __DEV__, warn in production
+
 ## MVP Feature Scope
 
 ### Must-Have
@@ -274,6 +309,8 @@ JWT_EXPIRES_IN=1h
 MONGODB_URI=mongodb://root:mongoose@localhost:27017/calchat?authSource=admin
 OPENAI_API_KEY=sk-proj-...
 USE_TEST_RESPONSES=false    # true = static test responses, false = real GPT AI
+LOG_LEVEL=debug             # debug | info | warn | error | fatal
+NODE_ENV=development        # development = pretty logs, production = JSON
 ```
 
 ## Current Implementation Status
@@ -299,6 +336,8 @@ USE_TEST_RESPONSES=false    # true = static test responses, false = real GPT AI
   - `ChatRepository` interface: updateMessage() added for respondedAction tracking
   - `GPTAdapter`: Full implementation with OpenAI GPT (gpt-5-mini model), function calling for calendar operations
   - `ai/utils/`: Provider-agnostic shared utilities (systemPrompt, toolDefinitions, toolExecutor, eventFormatter)
+  - `logging/`: Structured logging with pino, pino-http middleware, @Logged decorator
+  - All repositories and GPTAdapter decorated with @Logged for automatic method logging
 - **Stubbed (TODO):**
   - `AuthMiddleware.authenticate()`: Currently uses fake user for testing
   - `AuthController`: refresh(), logout()
@@ -323,7 +362,7 @@ USE_TEST_RESPONSES=false    # true = static test responses, false = real GPT AI
   - KeyboardAvoidingView for proper keyboard handling (iOS padding, Android height)
   - Auto-scroll to end on new messages and keyboard show
   - keyboardDismissMode="interactive" and keyboardShouldPersistTaps="handled"
-- `ApiClient`: get(), post(), put(), delete() implemented
+- `ApiClient`: get(), post(), put(), delete() implemented with request/response logging
 - `EventService`: getAll(), getById(), getByDateRange(), create(), update(), delete() - fully implemented
 - `ChatService`: sendMessage(), confirmEvent(), rejectEvent(), getConversations(), getConversation() - fully implemented with cursor pagination
 - `EventCardBase`: Shared base component with event layout (header, date/time/recurring icons, description) - used by both EventCard and ProposedEventCard

apps/client/package.json

@@ -34,6 +34,7 @@
     "react-dom": "19.1.0",
     "react-native": "0.81.5",
     "react-native-gesture-handler": "~2.28.0",
+    "react-native-logs": "^5.5.0",
     "react-native-reanimated": "~4.1.1",
     "react-native-safe-area-context": "5.6.0",
     "react-native-screens": "~4.16.0",

apps/client/src/logging/index.ts

@@ -0,0 +1 @@
+export { log, apiLogger, storeLogger } from "./logger";

apps/client/src/logging/logger.ts

@@ -0,0 +1,30 @@
+import { logger, consoleTransport } from "react-native-logs";
+
+const log = logger.createLogger({
+  levels: {
+    debug: 0,
+    info: 1,
+    warn: 2,
+    error: 3,
+  },
+  severity: __DEV__ ? "debug" : "warn",
+  transport: consoleTransport,
+  transportOptions: {
+    colors: {
+      debug: "white",
+      info: "blueBright",
+      warn: "yellowBright",
+      error: "redBright",
+    },
+  },
+  async: true,
+  dateFormat: "time",
+  printLevel: true,
+  printDate: true,
+  enabled: true,
+});
+
+export const apiLogger = log.extend("API");
+export const storeLogger = log.extend("Store");
+
+export { log };

apps/client/src/services/ApiClient.ts

@@ -1,4 +1,5 @@
 import { Platform } from "react-native";
+import { apiLogger } from "../logging";
 
 const API_BASE_URL =
   process.env.EXPO_PUBLIC_API_URL ||
@@ -19,20 +20,33 @@ async function request<T>(
   endpoint: string,
   options?: RequestOptions,
 ): Promise<T> {
-  const response = await fetch(`${API_BASE_URL}${endpoint}`, {
+  const start = performance.now();
-    method,
+  apiLogger.debug(`${method} ${endpoint}`);
-    headers: {
-      "Content-Type": "application/json",
-      ...options?.headers,
-    },
-    body: options?.body ? JSON.stringify(options.body) : undefined,
-  });
 
-  if (!response.ok) {
+  try {
-    throw new Error(`HTTP ${response.status}`);
+    const response = await fetch(`${API_BASE_URL}${endpoint}`, {
+      method,
+      headers: {
+        "Content-Type": "application/json",
+        ...options?.headers,
+      },
+      body: options?.body ? JSON.stringify(options.body) : undefined,
+    });
+
+    const duration = Math.round(performance.now() - start);
+
+    if (!response.ok) {
+      apiLogger.error(`${method} ${endpoint} - ${response.status} (${duration}ms)`);
+      throw new Error(`HTTP ${response.status}`);
+    }
+
+    apiLogger.debug(`${method} ${endpoint} - ${response.status} (${duration}ms)`);
+    return response.json();
+  } catch (error) {
+    const duration = Math.round(performance.now() - start);
+    apiLogger.error(`${method} ${endpoint} failed (${duration}ms): ${error}`);
+    throw error;
   }
-
-  return response.json();
 }
 
 export const ApiClient = {

apps/server/package.json

@@ -15,6 +15,8 @@
     "jsonwebtoken": "^9.0.3",
     "mongoose": "^9.1.1",
     "openai": "^6.15.0",
+    "pino": "^10.1.1",
+    "pino-http": "^11.0.0",
     "rrule": "^2.8.1"
   },
   "devDependencies": {
@@ -22,6 +24,7 @@
     "@types/express": "^5.0.6",
     "@types/jsonwebtoken": "^9.0.10",
     "@types/node": "^24.10.1",
+    "pino-pretty": "^13.1.3",
     "tsx": "^4.21.0",
     "typescript": "^5.9.3"
   }

apps/server/src/ai/GPTAdapter.ts

@@ -7,6 +7,7 @@ import {
   executeToolCall,
   ToolDefinition,
 } from "./utils";
+import { Logged } from "../logging";
 
 /**
  * Convert tool definitions to OpenAI format.
@@ -24,6 +25,7 @@ function toOpenAITools(
   }));
 }
 
+@Logged("GPTAdapter")
 export class GPTAdapter implements AIProvider {
   private client: OpenAI;
   private model: string;

apps/server/src/app.ts

@@ -3,7 +3,12 @@ import mongoose from "mongoose";
 import "dotenv/config";
 
 import { createRoutes } from "./routes";
-import { AuthController, ChatController, EventController } from "./controllers";
+import {
+  AuthController,
+  ChatController,
+  EventController,
+  httpLogger,
+} from "./controllers";
 import { AuthService, ChatService, EventService } from "./services";
 import {
   MongoUserRepository,
@@ -11,6 +16,7 @@ import {
   MongoChatRepository,
 } from "./repositories";
 import { GPTAdapter } from "./ai";
+import { logger } from "./logging";
 
 const app = express();
 const port = process.env.PORT || 3000;
@@ -18,6 +24,7 @@ const mongoUri = process.env.MONGODB_URI || "mongodb://localhost:27017/caldav";
 
 // Middleware
 app.use(express.json());
+app.use(httpLogger);
 
 // CORS - only needed for web browser development
 // Native mobile apps don't send Origin headers and aren't affected by CORS
@@ -86,7 +93,7 @@ app.post("/api/ai/test", async (req, res) => {
     });
     res.json(result);
   } catch (error) {
-    console.error("AI test error:", error);
+    logger.error({ error }, "AI test error");
     res.status(500).json({ error: String(error) });
   }
 });
@@ -95,13 +102,13 @@ app.post("/api/ai/test", async (req, res) => {
 async function start() {
   try {
     await mongoose.connect(mongoUri);
-    console.log("Connected to MongoDB");
+    logger.info("Connected to MongoDB");
 
     app.listen(port, () => {
-      console.log(`Server running on port ${port}`);
+      logger.info({ port }, "Server started");
     });
   } catch (error) {
-    console.error("Failed to start server:", error);
+    logger.fatal({ error }, "Failed to start server");
     process.exit(1);
   }
 }

apps/server/src/controllers/ChatController.ts

@@ -7,7 +7,10 @@ import {
   GetMessagesOptions,
 } from "@caldav/shared";
 import { ChatService } from "../services";
-import { AuthenticatedRequest } from "../middleware";
+import { createLogger } from "../logging";
+import { AuthenticatedRequest } from "./AuthMiddleware";
+
+const log = createLogger("ChatController");
 
 export class ChatController {
   constructor(private chatService: ChatService) {}
@@ -19,6 +22,7 @@ export class ChatController {
       const response = await this.chatService.processMessage(userId, data);
       res.json(response);
     } catch (error) {
+      log.error({ error, userId: req.user?.userId }, "Error processing message");
       res.status(500).json({ error: "Failed to process message" });
     }
   }
@@ -44,6 +48,7 @@ export class ChatController {
       );
       res.json(response);
     } catch (error) {
+      log.error({ error, conversationId: req.params.conversationId }, "Error confirming event");
       res.status(500).json({ error: "Failed to confirm event" });
     }
   }
@@ -59,6 +64,7 @@ export class ChatController {
       );
       res.json(response);
     } catch (error) {
+      log.error({ error, conversationId: req.params.conversationId }, "Error rejecting event");
       res.status(500).json({ error: "Failed to reject event" });
     }
   }
@@ -72,6 +78,7 @@ export class ChatController {
       const conversations = await this.chatService.getConversations(userId);
       res.json(conversations);
     } catch (error) {
+      log.error({ error, userId: req.user?.userId }, "Error getting conversations");
       res.status(500).json({ error: "Failed to get conversations" });
     }
   }
@@ -102,6 +109,7 @@ export class ChatController {
       if ((error as Error).message === "Conversation not found") {
         res.status(404).json({ error: "Conversation not found" });
       } else {
+        log.error({ error, conversationId: req.params.id }, "Error getting conversation");
         res.status(500).json({ error: "Failed to get conversation" });
       }
     }

apps/server/src/controllers/EventController.ts

@@ -1,6 +1,9 @@
 import { Response } from "express";
 import { EventService } from "../services";
-import { AuthenticatedRequest } from "../middleware";
+import { createLogger } from "../logging";
+import { AuthenticatedRequest } from "./AuthMiddleware";
+
+const log = createLogger("EventController");
 
 export class EventController {
   constructor(private eventService: EventService) {}
@@ -10,7 +13,7 @@ export class EventController {
       const event = await this.eventService.create(req.user!.userId, req.body);
       res.status(201).json(event);
     } catch (error) {
-      console.error("Error creating event:", error);
+      log.error({ error, userId: req.user?.userId }, "Error creating event");
       res.status(500).json({ error: "Failed to create event" });
     }
   }
@@ -27,7 +30,7 @@ export class EventController {
       }
       res.json(event);
     } catch (error) {
-      console.error("Error getting event:", error);
+      log.error({ error, eventId: req.params.id }, "Error getting event");
       res.status(500).json({ error: "Failed to get event" });
     }
   }
@@ -37,7 +40,7 @@ export class EventController {
       const events = await this.eventService.getAll(req.user!.userId);
       res.json(events);
     } catch (error) {
-      console.error("Error getting events:", error);
+      log.error({ error, userId: req.user?.userId }, "Error getting events");
       res.status(500).json({ error: "Failed to get events" });
     }
   }
@@ -69,7 +72,7 @@ export class EventController {
       );
       res.json(events);
     } catch (error) {
-      console.error("Error getting events by range:", error);
+      log.error({ error, start: req.query.start, end: req.query.end }, "Error getting events by range");
       res.status(500).json({ error: "Failed to get events" });
     }
   }
@@ -87,7 +90,7 @@ export class EventController {
       }
       res.json(event);
     } catch (error) {
-      console.error("Error updating event:", error);
+      log.error({ error, eventId: req.params.id }, "Error updating event");
       res.status(500).json({ error: "Failed to update event" });
     }
   }
@@ -104,7 +107,7 @@ export class EventController {
       }
       res.status(204).send();
     } catch (error) {
-      console.error("Error deleting event:", error);
+      log.error({ error, eventId: req.params.id }, "Error deleting event");
       res.status(500).json({ error: "Failed to delete event" });
     }
   }

apps/server/src/controllers/LoggingMiddleware.ts

@@ -0,0 +1,27 @@
+import pinoHttp from "pino-http";
+import { logger } from "../logging";
+
+export const httpLogger = pinoHttp({
+  logger,
+  customLogLevel: (_req, res, err) => {
+    if (res.statusCode >= 500 || err) return "error";
+    if (res.statusCode >= 400) return "warn";
+    return "info";
+  },
+  customSuccessMessage: (req, res) => {
+    return `${req.method} ${req.url} ${res.statusCode}`;
+  },
+  customErrorMessage: (req, _res, err) => {
+    return `${req.method} ${req.url} failed: ${err.message}`;
+  },
+  redact: ["req.headers.authorization"],
+  serializers: {
+    req: (req) => ({
+      method: req.method,
+      url: req.url,
+    }),
+    res: (res) => ({
+      statusCode: res.statusCode,
+    }),
+  },
+});

apps/server/src/controllers/index.ts

@@ -1,3 +1,5 @@
 export * from "./AuthController";
 export * from "./ChatController";
 export * from "./EventController";
+export * from "./AuthMiddleware";
+export * from "./LoggingMiddleware";

apps/server/src/logging/Logged.ts

@@ -0,0 +1,76 @@
+import { createLogger } from "./logger";
+
+export function Logged(name: string) {
+  const log = createLogger(name);
+
+  // eslint-disable-next-line @typescript-eslint/no-explicit-any
+  return function <T extends { new (...args: any[]): any }>(Constructor: T) {
+    return class extends Constructor {
+      // eslint-disable-next-line @typescript-eslint/no-explicit-any
+      constructor(...args: any[]) {
+        super(...args);
+
+        // Return a Proxy that intercepts method calls lazily
+        return new Proxy(this, {
+          get(target, propKey, receiver) {
+            const original = Reflect.get(target, propKey, receiver);
+
+            if (typeof original !== "function" || propKey === "constructor") {
+              return original;
+            }
+
+            // eslint-disable-next-line @typescript-eslint/no-explicit-any
+            const originalFn = original as (...args: any[]) => any;
+
+            // eslint-disable-next-line @typescript-eslint/no-explicit-any
+            return function (this: any, ...methodArgs: any[]) {
+              const start = performance.now();
+              const method = String(propKey);
+
+              // Pino's redact handles sanitization - just pass args directly
+              log.debug({ method, args: methodArgs }, `${method} started`);
+
+              const logCompletion = (err?: unknown) => {
+                const duration = Math.round(performance.now() - start);
+                if (err) {
+                  const message =
+                    err instanceof Error ? err.message : String(err);
+                  log.error(
+                    { method, duration, error: message },
+                    `${method} failed`,
+                  );
+                } else {
+                  log.info({ method, duration }, `${method} completed`);
+                }
+              };
+
+              try {
+                const result = originalFn.apply(this, methodArgs);
+
+                // Check if async - preserves sync/async nature of method
+                if (result instanceof Promise) {
+                  return result
+                    .then((val) => {
+                      logCompletion();
+                      return val;
+                    })
+                    .catch((err) => {
+                      logCompletion(err);
+                      throw err;
+                    });
+                }
+
+                // Synchronous completion
+                logCompletion();
+                return result;
+              } catch (err) {
+                logCompletion(err);
+                throw err;
+              }
+            };
+          },
+        });
+      }
+    };
+  };
+}

apps/server/src/logging/index.ts

@@ -0,0 +1,2 @@
+export { logger, createLogger, type Logger } from "./logger";
+export { Logged } from "./Logged";

apps/server/src/logging/logger.ts

@@ -0,0 +1,43 @@
+import pino from "pino";
+
+const isDevelopment = process.env.NODE_ENV !== "production";
+
+export const logger = pino({
+  level: process.env.LOG_LEVEL || (isDevelopment ? "debug" : "info"),
+  redact: {
+    paths: [
+      // Root level
+      "password",
+      "passwordHash",
+      "token",
+      // One level deep (e.g. user.password)
+      "*.password",
+      "*.passwordHash",
+      "*.token",
+      // In arrays (for 'args' in decorator)
+      "args[*].password",
+      "args[*].passwordHash",
+      "args[*].token",
+    ],
+    censor: "[REDACTED]",
+  },
+  transport: isDevelopment
+    ? {
+        target: "pino-pretty",
+        options: {
+          colorize: true,
+          translateTime: "SYS:HH:MM:ss",
+          ignore: "pid,hostname",
+        },
+      }
+    : undefined,
+  base: {
+    service: "caldav-server",
+  },
+});
+
+export function createLogger(module: string) {
+  return logger.child({ module });
+}
+
+export type Logger = pino.Logger;

apps/server/src/middleware/index.ts

@@ -1 +0,0 @@
-export * from "./AuthMiddleware";

apps/server/src/repositories/mongo/MongoChatRepository.ts

@@ -6,8 +6,10 @@ import {
   UpdateMessageDTO,
 } from "@caldav/shared";
 import { ChatRepository } from "../../services/interfaces";
+import { Logged } from "../../logging";
 import { ChatMessageModel, ConversationModel } from "./models";
 
+@Logged("MongoChatRepository")
 export class MongoChatRepository implements ChatRepository {
   // Conversations
   async getConversationsByUser(userId: string): Promise<Conversation[]> {

apps/server/src/repositories/mongo/MongoEventRepository.ts

@@ -1,7 +1,9 @@
 import { CalendarEvent, CreateEventDTO, UpdateEventDTO } from "@caldav/shared";
 import { EventRepository } from "../../services/interfaces";
+import { Logged } from "../../logging";
 import { EventModel } from "./models";
 
+@Logged("MongoEventRepository")
 export class MongoEventRepository implements EventRepository {
   async findById(id: string): Promise<CalendarEvent | null> {
     const event = await EventModel.findById(id);

apps/server/src/repositories/mongo/MongoUserRepository.ts

@@ -1,7 +1,9 @@
 import { User } from "@caldav/shared";
 import { UserRepository, CreateUserData } from "../../services/interfaces";
+import { Logged } from "../../logging";
 import { UserModel } from "./models";
 
+@Logged("MongoUserRepository")
 export class MongoUserRepository implements UserRepository {
   async findById(id: string): Promise<User | null> {
     throw new Error("Not implemented");

apps/server/src/routes/chat.routes.ts

@@ -1,6 +1,5 @@
 import { Router } from "express";
-import { ChatController } from "../controllers";
+import { ChatController, authenticate } from "../controllers";
-import { authenticate } from "../middleware";
 
 export function createChatRoutes(chatController: ChatController): Router {
   const router = Router();

apps/server/src/routes/event.routes.ts

@@ -1,6 +1,5 @@
 import { Router } from "express";
-import { EventController } from "../controllers";
+import { EventController, authenticate } from "../controllers";
-import { authenticate } from "../middleware";
 
 export function createEventRoutes(eventController: EventController): Router {
   const router = Router();

apps/server/tsconfig.json

@@ -7,7 +7,8 @@
     "strict": true,
     "esModuleInterop": true,
     "forceConsistentCasingInFileNames": true,
-    "skipLibCheck": true
+    "experimentalDecorators": true,
+    "emitDecoratorMetadata": true
   },
   "include": ["src"]
 }

package-lock.json

@@ -44,6 +44,7 @@
         "react-dom": "19.1.0",
         "react-native": "0.81.5",
         "react-native-gesture-handler": "~2.28.0",
+        "react-native-logs": "^5.5.0",
         "react-native-reanimated": "~4.1.1",
         "react-native-safe-area-context": "5.6.0",
         "react-native-screens": "~4.16.0",
@@ -69,6 +70,8 @@
         "jsonwebtoken": "^9.0.3",
         "mongoose": "^9.1.1",
         "openai": "^6.15.0",
+        "pino": "^10.1.1",
+        "pino-http": "^11.0.0",
         "rrule": "^2.8.1"
       },
       "devDependencies": {
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