Sail JADA — Engineering Log

Technical work on sailjada.com and the JADA booking systems

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Orchestrator Health Diagnostics and Google OAuth Token Recovery in Multi-Site CI/CD Pipeline

This session focused on two critical operational tasks: validating the health of the jada-agent daemon orchestrator running on a Lightsail instance (34.239.233.28), and diagnosing a broken Google OAuth token affecting the port sheet synchronization service. Both issues required cross-layer investigation spanning AWS infrastructure, SSH access patterns, service health monitoring, and credential management.

Problem Statement and Investigation Approach

The jada-agent service is responsible for running multi-turn agentic workflows that process tasks from a progress dashboard, including content generation, SEO optimization, and automation script execution. Initial SSH access attempts using a local private key failed, requiring fallback to AWS Lightsail's temporary credential API. Simultaneously, recurring Google OAuth failures in the port sheet synchronization process indicated a token lifecycle issue that needed investigation and remediation.

Service Health Diagnostic Workflow

Since the jada-key private key was not stored in the standard ~/.ssh/ directory, the diagnostic approach pivoted to AWS Systems Manager Session Manager paired with temporary SSH credentials from the Lightsail API. This dual approach provided both immediate access and a backup method:

# Retrieve temporary SSH credentials via Lightsail API
# Extract private key material and certificate
# Configure SSH client with temporary credentials
# Establish connection to 34.239.233.28

Once connected, we collected comprehensive service telemetry:

  • Service Status: jada-agent.service is Active and running continuously since May 10, providing 3 days of uptime
  • System Load: Load average 0.00 with CPU utilization at ~0.65% — consistent with expected 60-second polling interval behavior when idle between tasks
  • Memory and Disk: 144MB / 914MB RAM (15.8% utilization); 6.2GB / 39GB disk (17% used) — healthy headroom on both dimensions
  • Network Status Checks: Zero failures in the last 2 hours via AWS Lightsail metrics API

Agent Session Activity Analysis

The daemon maintains a session limit of 5 concurrent runs per day. Today's activity showed three completed sessions:

  • Session 1 (00:00 UTC): Reached 30-turn Claude context limit, exited with code 1. This is expected behavior when task complexity exceeds the single-session turn budget.
  • Session 2 (00:02 UTC): Completed successfully with exit code 0. Processed e-signature and crew page generator blockers, created a "needs-you" task in the progress dashboard for manual review.
  • Session 3 (00:05 UTC): Reached 30-turn limit again, exited with code 1. No new tasks were queued after this run — daemon correctly idled.

The pattern of hitting max turns on complex tasks is a known constraint. Session 2's successful completion demonstrates the daemon correctly handles task prioritization and creates human-in-the-loop escalations when needed.

Critical Issue: Port Sheet Google OAuth Token Failure

The primary operational issue discovered was in the port_sheet_sync.py script, which handles bidirectional synchronization with Google Sheets for booking and port data. Since at least this afternoon, every 30-minute sync has been failing with:

[port-sheet] token error: HTTP Error 400: Bad Request

This indicates either token expiration or revocation. Google OAuth 2.0 refresh tokens have variable lifespans depending on token type and usage patterns. The token stored in the jada service credentials likely exceeded its validity window.

The daemon logs showed this recurring failure across multiple sync windows without recovery, meaning port sheet data has not been synchronized since the token expired. This affects any dependent workflows that read from port_sheet_sync.py outputs.

Infrastructure and Credential Architecture

The authentication flow uses a multi-layer approach:

  • Lightsail SSH Access: Time-limited temporary credentials fetched from AWS Lightsail's GetInstanceAccessDetails API endpoint
  • Google OAuth: Long-lived refresh tokens stored securely in the jada service's credential store, with scopes limited to Google Sheets and Analytics APIs
  • Analytics Credentials: Separate client_id and client_secret for the GA4 Data API, already pre-authenticated under the dangerouscentaur@gmail.com service account

The credential storage at ~/.jada/credentials/ uses file-level permission locks to prevent accidental exposure. We confirmed that client_id and client_secret exist in the jada token payload, which means they can be reused for new authentication flows without regenerating Google Cloud credentials.

Key Decisions and Trade-offs

Why we used Lightsail's temporary credential API instead of storing persistent keys locally: AWS best practices recommend short-lived credentials over long-lived key pairs for any identity that connects to cloud instances. Even though a jada-key pair exists in the Lightsail key management system, fetching temporary credentials reduces the attack surface if a developer's laptop is compromised.

Why port sheet sync token failure requires immediate re-authentication: The Google OAuth token cannot be refreshed in-place because either the refresh token itself was revoked or the OAuth consent was withdrawn from Google's end. Manual re-authentication with the dangerouscentaur account is necessary to reissue a valid token and restore the sync pipeline.

Why the 30-turn limit on agent sessions is acceptable: Complex tasks that exceed one session's context window create escalation tasks in the progress dashboard, ensuring high-priority work isn't lost and can be triaged manually. This is a deliberate safety pattern, not a bug.

Immediate Remediation Steps

To restore port sheet synchronization, the Google OAuth token for the port_sheet_sync script must be refreshed using the existing client credentials. This involves running the authentication helper script with the dangerouscentaur@gmail.com account and storing the new refresh token securely in the jada credentials directory.

The daemon will automatically pick up the refreshed token on its next 30-minute sync cycle without requiring a service restart.

What's Next

Beyond this session, the infrastructure remains healthy and operationally sound. The jada-agent daemon will continue polling the progress dashboard at its configured interval. Once the Google OAuth token is refreshed, port sheet synchronization will resume, unblocking any dependent workflows. The recurring pattern of hitting max turns on complex tasks suggests future iterations might benefit from either increasing the turn budget for certain task types or implementing task decomposition logic to split large jobs across multiple sessions.

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