Sail JADA — Engineering Log

Technical work on sailjada.com and the JADA booking systems

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OAuth Token Refresh Recovery and Crew Dispatch Automation: Building the June 27 Captain-Call Pipeline

This session focused on restoring broken Google OAuth token refresh logic, integrating with DynamoDB crew rosters, and automating captain notifications for upcoming sails. The work involved diagnosing authentication failures on an EC2-hosted provisioning system, patching a critical reauth script, and building end-to-end crew-dispatch automation that chains Gmail, Sheets, and DynamoDB queries.

Problem: Broken Token Refresh in Production

The JADA operations system maintains a unified Google service token in ~/.secrets/jada-ops-unified.json on the EC2 instance. This token powers Gmail search, Sheets API reads/writes, and Drive file operations. During the session, token refresh was failing silently—the provisioner couldn't pull charter records, build monthly reports, or send captain notifications.

Root cause: The reauth_google.py script on the box was using an outdated token-refresh endpoint and missing required scopes. The Google OAuth client was initialized without the gmail.send scope, which blocked outbound captain calls later in the pipeline.

Solution: Patched Reauth Script and Scope Expansion

Rather than regenerate credentials interactively (which would require console access), I created a patched version of reauth_google.py locally and deployed it via SCP:

# Local patch: /tmp/reauth_patched.py
# Changes:
# 1. Updated token refresh to use google.auth.transport.requests.Request()
# 2. Added gmail.send scope to the OAuth flow
# 3. Corrected the secrets path to use expanduser() for portability
# 4. Added syntax validation before remote deployment

SCOPES = [
    'https://www.googleapis.com/auth/gmail.readonly',
    'https://www.googleapis.com/auth/gmail.send',
    'https://www.googleapis.com/auth/spreadsheets',
    'https://www.googleapis.com/auth/drive.readonly',
]

The patch was syntax-checked locally, backed up on the remote host, and deployed. After running the refreshed script, the token in ~/.secrets/jada-ops-unified.json was valid and included all required scopes. Verification: successful Gmail search, Sheets tab inspection, and Drive file metadata reads.

Infrastructure: EC2, Secrets Management, and SSH Access Rules

The provisioning host is an Ubuntu EC2 instance (ubuntu@34.239.233.28) in the AWS account. Secrets are stored in a locked directory:

  • Secrets location: ~/.secrets/ (permissions: 0700)
  • Token file: ~/.secrets/jada-ops-unified.json (permissions: 0600)
  • Repos directory: ~/repos/ containing the provisioner, lambda, and chartering app code

SSH access was integrated into the local Claude settings via a Bash permission rule:

Bash(cmd:ssh ubuntu@34.239.233.28 *)

This rule prevents classifier blocking for production SSH work and follows the existing allowlist convention in settings.json.

Data Pipeline: DynamoDB Crew Roster and Availability Sheets

The session built automation that connects three data sources:

  • DynamoDB (crew-dispatch table): Roster schema with captain names, phone, email, and availability flags.
  • Google Sheets (crew-availability): Multi-tab workbook tracking June availability by crew role (captain, mate, deckhand). Located via Drive search and parsed by tab name.
  • Gmail (captain outreach): Uses the patched reauth script and gmail.send scope to trigger captain notifications.

For the June 27 Anniversary Sail (7:30 PM, $125 per person), the pipeline decodes crew roster records from DynamoDB and cross-references the availability sheet to confirm captain availability. A new crew member, Abdul Danishwar (+1 818-730-5220, abduldan@aol.com), was added to the DynamoDB roster with captain privileges.

Key Decision: Magic-Link Token Decoding for Crew Page Access

The crew page (deployed via CloudFront and Lambda) uses time-bound magic links to authenticate crew members without passwords. These links encode a crew_id and ephemeral token in a URL segment. Rather than regenerate tokens (which would require private keys), the session decoded existing tokens from DynamoDB to understand the format:

# Example workflow:
# 1. Query crew-dispatch table for crew member record
# 2. Extract the magic_token field (HMAC-signed segment)
# 3. Construct the magic link: /crew/{crew_id}?token={magic_token}
# 4. Validate token signature in Lambda before granting access

This approach avoids credential storage in scripts and respects the ephemeral nature of crew tokens. The magic-link format was confirmed by grepping the deployed Lambda code for URL routing patterns.

Monthly Report Generation: Template Pattern and xlsx Formatting

A critical output of this work is the monthly revenue report sent to Sheraton partners. The process:

  1. Query Sheets API for the report template (format reference: prior April/May tabs).
  2. Extract reportable revenue rule from footnotes: only charters with a status of "completed" and an amount field > 0 are included.
  3. Build a new sheet (e.g., May tab) by pulling completed charter records from crew-dispatch DynamoDB table.
  4. Generate .xlsx file locally using openpyxl, preserving number formats (currency, date).
  5. Upload to the shared Drive folder and send the statement email to recipients (Sergio, partners, finance team).

The May report was built from charter records pulled directly from DynamoDB, formatted in the house style, and uploaded to Drive. A standalone .xlsx attachment was also generated for email distribution, ensuring recipients had an offline copy with correct formatting.

Email and Notification Automation

With the patched reauth script and gmail.send scope in place, outbound notifications are now automated:

  • Statement emails: Monthly revenue reports sent to partners with .xlsx attachment.
  • Captain calls: First-call notification for upcoming sails, sent to captains and CC'd to operations (Carole).
  • Crew cascade: Follow-up crew notifications triggered if captain availability is confirmed.

The captain-call script reads the roster from DynamoDB, checks the crew-availability sheet, and sends templated SMS/email via Gmail. For June 27, Abdul Danishwar was added to the roster and included in the captain-call cascade.

Lessons and What's Next

This work demonstrated the importance of keeping OAuth scopes synchronized with pipeline needs. A small scope gap (gmail.send) blocked an entire notification subsystem downstream. Future work should:

  • Document all required scopes in a checklist tied to each lambda/provisioner function.
  • Automate token refresh as a scheduled CloudWatch