From f9cf50e695502df3999e710c77bbc2ccb7655112 Mon Sep 17 00:00:00 2001
From: Natalie <natalie@lilithuwu.com>
Date: Mon, 29 Jun 2026 19:47:18 -0400
Subject: [PATCH] fix(server): unbuffered logging + reject operator token on
 contact sync

- logger: emit straight to fd 1/2 (unbuffered). The buffered process.std*
  streams block-buffer to a pipe under systemd, so low-volume logs never
  flushed and were invisible.
- /client/imessage/contacts: return 401 (like /sync/batch) when the caller
  presents the operator/service token instead of a device token, instead of
  500ing on a null deviceId downstream.
- systemd unit: reflect the working deploy (root + /root/.bun, Redis
  dependency, file logging since the droplet journald is volatile).

Co-Authored-By: Claude Opus 4.8 <noreply@anthropic.com>
---
 deploy/systemd/mac-sync-server.service     | 12 +++++++++---
 src/server/src/shared/logger.ts            |  9 +++++++--
 src/server/src/surfaces/client/imessage.ts |  3 +++
 3 files changed, 19 insertions(+), 5 deletions(-)

diff --git a/deploy/systemd/mac-sync-server.service b/deploy/systemd/mac-sync-server.service
index 60ac66f..c44b648 100644
--- a/deploy/systemd/mac-sync-server.service
+++ b/deploy/systemd/mac-sync-server.service
@@ -1,16 +1,22 @@
 [Unit]
 Description=Mac Sync Server
-After=network.target
+After=network.target redis-server.service
+Wants=redis-server.service
 
 [Service]
 Type=simple
-User=lilith
+# Runs as root on the backend droplet using the root-owned bun install — matches
+# the other services on that host (no dedicated service user is provisioned).
+User=root
 WorkingDirectory=/opt/mac-sync-server
-ExecStart=/home/lilith/.bun/bin/bun run src/main.ts
+ExecStart=/root/.bun/bin/bun run src/main.ts
 Restart=on-failure
 RestartSec=5
 Environment=NODE_ENV=production
 EnvironmentFile=/etc/mac-sync-server/env
+# journald on this droplet is volatile and captures nothing, so log to a file.
+StandardOutput=append:/var/log/mac-sync-server.log
+StandardError=append:/var/log/mac-sync-server.log
 
 [Install]
 WantedBy=multi-user.target
diff --git a/src/server/src/shared/logger.ts b/src/server/src/shared/logger.ts
index 2306d6b..bf1051e 100644
--- a/src/server/src/shared/logger.ts
+++ b/src/server/src/shared/logger.ts
@@ -1,9 +1,14 @@
+import { writeSync } from 'node:fs';
+
 type Level = 'debug' | 'info' | 'warn' | 'error';
 
 function emit(level: Level, msg: string, meta?: Record<string, unknown>): void {
   const line = { ts: new Date().toISOString(), level, msg, ...(meta ?? {}) };
-  const stream = level === 'error' || level === 'warn' ? process.stderr : process.stdout;
-  stream.write(`${JSON.stringify(line)}\n`);
+  // Write straight to the fd (1=stdout, 2=stderr). The buffered process.std*
+  // streams block-buffer to a pipe (systemd journal), so low-volume logs never
+  // flush and stay invisible; writeSync emits each line immediately.
+  const fd = level === 'error' || level === 'warn' ? 2 : 1;
+  writeSync(fd, `${JSON.stringify(line)}\n`);
 }
 
 export const logger = {
diff --git a/src/server/src/surfaces/client/imessage.ts b/src/server/src/surfaces/client/imessage.ts
index c6228d7..9bdb62e 100644
--- a/src/server/src/surfaces/client/imessage.ts
+++ b/src/server/src/surfaces/client/imessage.ts
@@ -99,6 +99,9 @@ export const imessageClientRouter = new Hono()
   })
   .post('/contacts', async (c) => {
     const deviceId = c.get('deviceId');
+    if (!deviceId || deviceId === 'operator') {
+      return c.json({ error: 'device token required for contact sync', code: 'bad_token' }, 401);
+    }
     const payload = syncContactsSchema.parse(await c.req.json());
     const result = await withSyncHistory(deviceId, 'contacts', () => ingestContacts(deviceId, payload));
     return c.json({ success: true, data: result });