docs: update backlog tasks

Author: pythoninthegrass

backlog/tasks/task-019 - Fix-deployment-crash-invalid-private-key-in-sign_jwt.py.md

@@ -0,0 +1,52 @@
+---
+id: TASK-019
+title: 'Fix deployment crash: invalid private key in sign_jwt.py'
+status: To Do
+assignee: []
+created_date: '2026-03-16 23:02'
+labels:
+  - deployment
+  - dokploy
+dependencies: []
+references:
+  - 'app/sign_jwt.py:50'
+  - 'app/main.py:23'
+  - 'app/meetup_query.py:16'
+  - CLAUDE.local.md
+priority: high
+---
+
+## Description
+
+<!-- SECTION:DESCRIPTION:BEGIN -->
+Gunicorn workers crash on startup with `ValueError: Invalid private key` in `sign_jwt.py:50`.
+
+**Stack trace summary:**
+- `main.py:23` imports `meetup_query`
+- `meetup_query.py:16` imports `sign_jwt.main`
+- `sign_jwt.py:50` calls `serialization.load_pem_private_key()` which raises `ValueError: Invalid private key`
+
+Both workers (pid 12, 13) fail to boot, causing gunicorn master to shut down.
+
+**Likely causes:**
+1. The `MEETUP_PRIVATE_KEY` env var is missing or empty on the Dokploy deployment
+2. The private key value has been corrupted (e.g., newlines stripped, base64 encoding issues when pushed via `ic --env prod env`)
+3. The key is being loaded at module level (import time), so any env var issue is fatal with no graceful error handling
+
+**Environment:**
+- Host: 85.31.233.80 (Dokploy)
+- Logs from: 2026-03-16T22:59:21Z
+
+**Investigation steps:**
+1. Check if the private key env var is set: `ic --env prod exec web` and inspect env
+2. Verify the key format — PEM keys need literal newlines, not `\n` escape sequences
+3. Compare the deployed key value against the local `.env` value
+4. If the key is correct but mangled, consider base64-encoding it and decoding at runtime
+<!-- SECTION:DESCRIPTION:END -->
+
+## Acceptance Criteria
+<!-- AC:BEGIN -->
+- [ ] #1 Gunicorn workers start successfully without ValueError on Dokploy
+- [ ] #2 Private key is correctly loaded from environment in the deployed container
+- [ ] #3 sign_jwt.py handles missing/invalid key gracefully at import time (log error instead of crash)
+<!-- AC:END -->