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Documenso Prod Checklist

DevOps & Security
documenso-prod-checklist

Documenso Prod Checklist is an Agent Skill for devops & security published in the Dicklesworthstone/pi_agent_rust repository on GitHub: a SKILL.md instruction file an AI agent can load to do this task.

Execute Documenso production deployment checklist and rollback procedures. Use when deploying Documenso integrations to production, preparing for launch, or implementing go-live procedures. Trigger with phrases like "documenso production", "deploy documenso", "documenso go-live", "documenso launch checklist".

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How to use this skill

Bring this guide into your coding agent with a prompt tailored to the tool you use.

  1. Open your project in Codex.
  2. Copy and paste the prompt below.
  3. Review files and risks before approving any action.
Prompt to paste
Inspect the Agent Skill at https://github.com/Dicklesworthstone/pi_agent_rust/blob/HEAD/tests/ext_conformance/artifacts/plugins-community/plugins/saas-packs/documenso-pack/skills/documenso-prod-checklist/SKILL.md and all supporting files. Report provenance, permissions, scripts, dependencies, and security risks. Propose an exact installation into .agents/skills/documenso-prod-checklist, but wait for my approval before writing files or running scripts.

Copying this prompt does not install or run the skill. Review third-party files before use.

Documenso Production Checklist

Overview

Complete checklist for deploying Documenso document signing integrations to production.

Prerequisites

  • Staging environment tested and verified
  • Production API keys available
  • Deployment pipeline configured
  • Monitoring and alerting ready

Pre-Deployment Checklist

Configuration

  • Production API key generated (separate from staging)
  • API key stored in secure vault (not in code)
  • Environment variables configured in deployment platform
  • Webhook endpoint URL uses HTTPS
  • Webhook secret configured
  • Base URL correct for environment

Code Quality

  • All tests passing (npm test)
  • No hardcoded credentials or API keys
  • Error handling covers all Documenso error types
  • Rate limiting/backoff implemented
  • Logging is production-appropriate (no sensitive data)
  • TypeScript strict mode enabled

Security

  • API keys have minimal required permissions
  • Webhook signature verification implemented
  • Input validation on all user inputs
  • File upload validation (type, size)
  • Signing URLs not exposed in logs
  • Audit logging enabled

Infrastructure

  • Health check endpoint includes Documenso connectivity
  • Monitoring/alerting configured for errors
  • Circuit breaker pattern implemented
  • Graceful degradation for Documenso outages

Documentation

  • Incident runbook created
  • API key rotation procedure documented
  • Rollback procedure documented
  • On-call escalation path defined

Deployment Procedure

Step 1: Pre-flight Checks

# Verify staging health
curl -f https://staging.yourapp.com/health

# Verify Documenso API status
curl -s https://status.documenso.com/api/v2/status.json | jq '.status'

# Run final test suite
npm run test:integration

Step 2: Deploy with Gradual Rollout

# Deploy to production (canary - 10%)
kubectl apply -f k8s/production.yaml
kubectl set image deployment/signing-service app=image:new --record
kubectl rollout pause deployment/signing-service

# Monitor canary for 10 minutes
echo "Monitoring canary deployment..."
sleep 600

# Check error rates
kubectl logs -l app=signing-service --since=10m | grep -c "ERROR"

# If healthy, continue to 50%
kubectl rollout resume deployment/signing-service
kubectl rollout pause deployment/signing-service
sleep 300

# Complete rollout to 100%
kubectl rollout resume deployment/signing-service
kubectl rollout status deployment/signing-service

Step 3: Health Check Implementation

// src/health.ts
import { getDocumensoClient } from "./documenso/client";

interface HealthStatus {
  status: "healthy" | "degraded" | "unhealthy";
  checks: {
    documenso: {
      connected: boolean;
      latencyMs: number;
      error?: string;
    };
    database?: {
      connected: boolean;
      latencyMs: number;
    };
  };
  version: string;
}

export async function healthCheck(): Promise<HealthStatus> {
  const checks: HealthStatus["checks"] = {
    documenso: { connected: false, latencyMs: 0 },
  };

  // Test Documenso connectivity
  const docStart = Date.now();
  try {
    const client = getDocumensoClient();
    await client.documents.findV0({ perPage: 1 });
    checks.documenso = {
      connected: true,
      latencyMs: Date.now() - docStart,
    };
  } catch (error: any) {
    checks.documenso = {
      connected: false,
      latencyMs: Date.now() - docStart,
      error: error.message,
    };
  }

  // Determine overall status
  const allHealthy = checks.documenso.connected;
  const anyFailed = !checks.documenso.connected;

  return {
    status: allHealthy ? "healthy" : anyFailed ? "unhealthy" : "degraded",
    checks,
    version: process.env.APP_VERSION ?? "unknown",
  };
}

// Express endpoint
app.get("/health", async (req, res) => {
  const health = await healthCheck();
  const statusCode = health.status === "unhealthy" ? 503 : 200;
  res.status(statusCode).json(health);
});

Step 4: Monitoring Setup

// Monitor key metrics
interface DocumensoMetrics {
  requestsTotal: number;
  errorsTotal: number;
  latencyP50Ms: number;
  latencyP99Ms: number;
  rateLimitHits: number;
}

class MetricsCollector {
  private latencies: number[] = [];
  private errors = 0;
  private requests = 0;
  private rateLimits = 0;

  recordRequest(latencyMs: number, success: boolean): void {
    this.requests++;
    this.latencies.push(latencyMs);
    if (!success) this.errors++;

    // Keep last 1000 latencies
    if (this.latencies.length > 1000) {
      this.latencies = this.latencies.slice(-1000);
    }
  }

  recordRateLimit(): void {
    this.rateLimits++;
  }

  getMetrics(): DocumensoMetrics {
    const sorted = [...this.latencies].sort((a, b) => a - b);
    return {
      requestsTotal: this.requests,
      errorsTotal: this.errors,
      latencyP50Ms: sorted[Math.floor(sorted.length * 0.5)] ?? 0,
      latencyP99Ms: sorted[Math.floor(sorted.length * 0.99)] ?? 0,
      rateLimitHits: this.rateLimits,
    };
  }
}

// Export to Prometheus/Datadog/etc
app.get("/metrics", (req, res) => {
  const metrics = metricsCollector.getMetrics();
  res.json(metrics);
});

Step 5: Alert Configuration

AlertConditionSeverityAction
API Down5xx errors > 10/minP1Page on-call
High Latencyp99 > 5000msP2Investigate
Rate Limited429 errors > 5/minP2Reduce throughput
Auth Failures401/403 errors > 0P1Check API key
Webhook Failures4xx/5xx on webhookP2Check endpoint
# Example Datadog alert config
alerts:
  - name: documenso_api_errors
    query: sum(last_5m):sum:documenso.errors{env:production} > 10
    message: "High Documenso API error rate"
    priority: P1

  - name: documenso_high_latency
    query: avg(last_5m):avg:documenso.latency.p99{env:production} > 5000
    message: "Documenso API latency elevated"
    priority: P2

  - name: documenso_rate_limits
    query: sum(last_5m):sum:documenso.rate_limits{env:production} > 5
    message: "Hitting Documenso rate limits"
    priority: P2

Rollback Procedure

Immediate Rollback

# Kubernetes rollback
kubectl rollout undo deployment/signing-service
kubectl rollout status deployment/signing-service

# Verify rollback
kubectl get pods -l app=signing-service
curl -f https://yourapp.com/health

Feature Flag Rollback

// Use feature flags to disable Documenso features
const documensoEnabled = await featureFlags.isEnabled("documenso_signing");

if (!documensoEnabled) {
  throw new Error("Document signing temporarily unavailable");
}

Post-Deployment Verification

# Run smoke tests
npm run test:smoke

# Verify document creation
curl -X POST https://yourapp.com/api/documents \
  -H "Authorization: Bearer $USER_TOKEN" \
  -H "Content-Type: application/json" \
  -d '{"title":"Test Document"}'

# Verify webhook delivery
# Check webhook logs in Documenso dashboard

# Monitor for 30 minutes
watch -n 30 'curl -s https://yourapp.com/health | jq'

Output

  • Deployed Documenso integration
  • Health checks passing
  • Monitoring active
  • Rollback procedure tested

Error Handling

AlertConditionResponse
Deploy failedCI/CD errorCheck logs, retry
Health check failedDocumenso downImplement degraded mode
Rollback neededError spikeExecute rollback
Rate limits hitToo many requestsReduce throughput

Resources

Next Steps

For version upgrades, see documenso-upgrade-migration.