Staging Deploy

Staging Deployment Skill

Purpose: Deploy to staging environment safely and correctly - this is the automation wrapper.

When to Use:

• After Phase 5 validation passes
• When deploying new features for testing
• After hotfixes that need staging verification
• When requested by user/orchestrator

Background Documentation: See /docs/functional-areas/deployment/staging-deployment-guide.md for context and manual procedures.

🚨 SINGLE SOURCE OF TRUTH

This skill is the ONLY automated deployment procedure.

Division of responsibility:

• This skill: Executable automation (bash script)
• Deployment guide (/docs/functional-areas/deployment/staging-deployment-guide.md): Context, manual procedures, troubleshooting

DO NOT duplicate deployment automation in:

• ❌ Agent definitions
• ❌ Lessons learned (reference this skill instead)
• ❌ Process documentation (already has guide, references this skill)

How to Use This Skill

Executable Script: execute.sh

# From project root - with confirmation prompt
bash .claude/skills/staging-deploy/execute.sh

# Skip confirmation prompt (for automation)
SKIP_CONFIRMATION=true bash .claude/skills/staging-deploy/execute.sh

What the script does:

1. Shows pre-flight information (purpose, when/when NOT to use, shared server warning)
2. Requires confirmation before proceeding (skippable with env var)
3. Validates prerequisites:
   • Tests passing (requires 90%+ pass rate - standardized format)
   • Git clean (no uncommitted changes)
   • Branch verification (main or staging recommended)
   • SSH key accessible
   • Docker running
   • Registry access check
4. Builds production images (API and Web) with proper tagging
5. Pushes to DigitalOcean Container Registry (:latest and :git-sha tags)
6. Tests server connectivity
7. Pulls new images on staging server
8. Deploys containers (with verification they were actually recreated)
9. Runs health checks (Web, API, Database)
10. Runs smoke tests (homepage, events API)
11. Reports deployment summary

Script includes comprehensive safety checks - it will not run blindly and verifies prerequisites before deployment.

Rollback Procedure

Separate skill: staging-rollback.md

Quick rollback:

ssh -i /home/chad/.ssh/id_ed25519_witchcityrope witchcity@104.131.165.14
cd /opt/witchcityrope/staging

# Pull and restart previous :latest images
docker-compose -f docker-compose.staging.yml pull
docker-compose -f docker-compose.staging.yml up -d

# Or specify previous SHA
# docker-compose -f docker-compose.staging.yml pull witchcityrope-api:<previous-sha>
# docker-compose -f docker-compose.staging.yml up -d

Critical Deployment Notes

⚠️ Shared Server Warning

IMPORTANT: Server hosts multiple applications.

NEVER DO:

# ❌ WRONG - Stops ALL containers on server
docker stop $(docker ps -q)
docker-compose down

ALWAYS DO:

# ✅ RIGHT - Only affects WitchCityRope containers
docker-compose -f docker-compose.staging.yml down
docker-compose -f docker-compose.staging.yml up -d

🚨 Image Tagging Convention

Image Tagging: The skill automatically tags images as :latest for staging deployment.

Why: docker-compose.staging.yml uses image: ${REGISTRY}/witchcityrope-api:${IMAGE_TAG:-latest} which defaults to latest.

Note: Use the staging-deploy skill for all builds - it handles correct tagging automatically.

Common Issues & Solutions

Issue: Build fails locally

Cause: Missing dependencies, compilation errors

Solution:

1. Fix build errors
2. Test locally first: docker build -f apps/api/Dockerfile .
3. Ensure all tests passing before deploying

Issue: Push to registry fails

Cause: Docker not logged into DigitalOcean registry

Solution:

# Login to DO registry (one-time)
doctl registry login

Issue: Health checks fail after deployment

Cause: Services need more time, or deployment has errors

Solution:

1. Wait longer (skill waits 30 seconds)
2. Check logs via SSH to server and inspect container logs
3. If serious: Rollback

Issue: Smoke tests fail

Cause: Specific endpoints broken

Solution:

1. Review which endpoint failed
2. Check API logs for errors
3. Consider rollback if critical functionality broken

Integration with Agents

git-manager / librarian

After Phase 5 validation:

I'll deploy to staging for testing.

Skill is invoked automatically

Result: Code deployed to staging safely

test-executor

After successful test run:

All tests passed. Staging deployment can proceed.

Integration with Process Documentation

Deployment guide should reference this skill:

# Staging Deployment Process

After Phase 5 validation passes:

1. Use `staging-deploy` skill (automated)
2. Skill handles:
   - Build verification
   - Image push
   - Server deployment
   - Health checks
   - Smoke tests
3. Manual testing of critical flows
4. If issues: Use `staging-rollback` skill

**Automation**: `/.claude/skills/staging-deploy.md`
**Manual procedures**: This guide (for troubleshooting)

Output Format

{
  "stagingDeploy": {
    "status": "success",
    "timestamp": "2025-11-04T15:30:00Z",
    "gitSha": "abc123f",
    "build": {
      "api": "success",
      "web": "success"
    },
    "registry": {
      "api": "pushed",
      "web": "pushed",
      "tags": ["latest", "abc123f"]
    },
    "deployment": {
      "server": "104.131.165.14",
      "containersRestarted": true,
      "startTime": "2025-11-04T15:28:00Z",
      "endTime": "2025-11-04T15:30:00Z",
      "duration": "2m"
    },
    "healthChecks": {
      "web": "healthy",
      "api": "healthy",
      "database": "healthy"
    },
    "smokeTests": {
      "homepage": "pass",
      "eventsApi": "pass",
      "passed": 2,
      "failed": 0
    },
    "url": "https://staging.notfai.com",
    "rollbackAvailable": true,
    "previousSha": "def456g"
  }
}

On failure:

{
  "stagingDeploy": {
    "status": "failure",
    "phase": "health_checks",
    "error": "API health check failed",
    "action": "Review logs and consider rollback",
    "rollbackCommand": "bash .claude/skills/staging-rollback.md"
  }
}

Maintenance

This skill is the automation wrapper.

Division of labor:

• This skill: Executable bash script (automation)
• Deployment guide: Context, manual steps, troubleshooting

To update deployment procedure:

1. If automation changes: Update THIS skill
2. If context/background changes: Update deployment guide
3. Test changes before committing

To verify no duplication:

• Use single-source-validator skill to check for duplicated commands

Version History

• 2025-11-05: Fixed reliability - replaced SSH heredocs with direct commands, added container age verification
• 2025-11-04: Created as automation wrapper for staging deployment

Remember: This skill automates deployment. The deployment guide provides context and manual procedures for troubleshooting.