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SSL/HTTPS Testing Guide

Status: ✅ SSL Automation Completed - This guide documents the completed SSL automation implementation and provides testing procedures for the automated SSL/HTTPS workflow in the Torrust Tracker Demo. The two-phase SSL automation is now fully operational with self-signed certificates for local testing.

Table of Contents

Overview

Status: ✅ SSL Automation Completed (July 30, 2025)

The SSL/HTTPS automation has been fully implemented and is working end-to-end:

  1. ✅ Phase 1: Fully automated HTTP-only deployment (COMPLETED)
  2. ✅ Phase 2: Automated SSL/HTTPS deployment with self-signed certificates (COMPLETED)

Architecture Components (All Implemented)

  • HTTP Template: infrastructure/config/templates/application/nginx/nginx-http.conf.tpl
  • HTTPS Template:
    infrastructure/config/templates/application/nginx/nginx-https-selfsigned.conf.tpl
  • SSL Scripts: Located in application/share/bin/ssl-*.shIMPLEMENTED
  • Pebble Test Environment: application/compose.test.yaml

Working Tree Deployment for Testing

Important: For local testing, the deployment script automatically uses rsync --filter=':- .gitignore' to copy the working tree, including uncommitted and untracked files (while respecting .gitignore). This means all new SSL scripts, nginx templates, and Pebble configuration files are automatically copied to the VM during make app-deploy ENVIRONMENT=local, even if they are not yet committed to git.

This makes the testing workflow seamless - you can create new SSL scripts, test them locally, and deploy them immediately without needing to commit first.

Prerequisites

System Requirements

  • Local testing infrastructure set up (see Quick Start Guide)
  • Docker and Docker Compose installed
  • OpenTofu/Terraform configured
  • SSH access to test VMs

Required Tools

# Verify required tools are installed
make install-deps
make infra-config-local

# Test infrastructure prerequisites
make infra-test-prereq

Environment Setup

# Ensure you have the correct environment configured
cd /path/to/torrust-tracker-demo

# Check current environment configuration
ls -la infrastructure/config/environments/
cat infrastructure/config/environments/local.env

Phase 1: HTTP-Only Deployment Testing

Test 1: Template Processing

Purpose: Verify that the nginx HTTP template processes correctly with environment variables.

# Load environment variables
source infrastructure/config/environments/local.env

# Export DOLLAR variable for nginx variables
export DOLLAR='$'

# Test template processing
envsubst < infrastructure/config/templates/application/nginx/nginx-http.conf.tpl > /tmp/test-nginx-http.conf

# Verify output
cat /tmp/test-nginx-http.conf

Expected Results:

  • Domain names should be substituted: tracker.test.local, grafana.test.local
  • Nginx variables should be preserved: $proxy_add_x_forwarded_for, $host, etc.
  • Configuration should be valid nginx syntax

Validation Commands:

# Check domain substitution
grep -E "(tracker|grafana)\.test\.local" /tmp/test-nginx-http.conf

# Check nginx variable preservation
grep -E "\\\$proxy_add_x_forwarded_for|\\\$host|\\\$scheme" /tmp/test-nginx-http.conf

# Basic nginx syntax check (if nginx is installed locally)
nginx -t -c /tmp/test-nginx-http.conf 2>/dev/null && \
  echo "Syntax OK" || echo "Syntax check skipped (nginx not available)"

Test 2: Infrastructure Deployment

Purpose: Test the complete infrastructure deployment with HTTP-only configuration.

# Deploy infrastructure
make infra-apply

# Deploy application (includes nginx HTTP config generation)
make app-deploy

# Check deployment status
make infra-status

Expected Results:

  • VM should be provisioned successfully
  • Application should deploy without errors
  • HTTP services should be accessible

Validation Commands:

# Get VM IP
VM_IP=$(cd infrastructure/terraform && tofu output -raw vm_ip)
echo "VM IP: $VM_IP"

# Test HTTP endpoints
curl -s "http://$VM_IP/api/health_check" | jq
curl -s "http://$VM_IP/" | head -5

# Check nginx configuration on VM
ssh torrust@$VM_IP "cat /var/lib/torrust/proxy/etc/nginx-conf/nginx.conf" | head -20

Test 3: Service Health Validation

Purpose: Verify all services are running and responding correctly.

# Run health check
make app-health-check

# Manual service checks
ssh torrust@$VM_IP \
  "docker compose -f /home/torrust/github/torrust/torrust-tracker-demo/application/compose.yaml ps"

Expected Results:

  • All Docker services should be running
  • Health check endpoints should return success
  • Tracker and Grafana should be accessible via HTTP

Phase 2: SSL/HTTPS Enablement Testing

Test 4: SSL Script Validation

Purpose: Verify SSL scripts are executable and properly configured.

# Check SSL scripts exist and are executable
ls -la application/share/bin/ssl-*.sh

# Test script help/usage
application/share/bin/ssl-setup.sh --help
application/share/bin/ssl-validate-dns.sh --help
application/share/bin/ssl-generate.sh --help
application/share/bin/ssl-configure-nginx.sh --help
application/share/bin/ssl-activate-renewal.sh --help

Expected Results:

  • All SSL scripts should be present and executable
  • Help/usage information should be displayed correctly

Test 5: DNS Validation Script

Purpose: Test the DNS validation functionality.

# Test DNS validation for local domains
ssh torrust@$VM_IP \
  "cd /home/torrust/github/torrust/torrust-tracker-demo && \
   ./application/share/bin/ssl-validate-dns.sh test.local"

Expected Results:

  • For local testing, DNS validation may fail (expected)
  • Script should provide clear feedback about DNS status
  • No critical errors should occur

Test 6: HTTPS Template Processing

Purpose: Verify the HTTPS extension template processes correctly.

# Test HTTPS template processing
source infrastructure/config/environments/local.env
export DOLLAR='$'

envsubst < infrastructure/config/templates/application/nginx/nginx-https-extension.conf.tpl > /tmp/test-nginx-https.conf

# Verify output
cat /tmp/test-nginx-https.conf

Expected Results:

  • Domain names should be substituted in SSL certificate paths
  • Nginx variables should be preserved
  • SSL configuration should be complete and valid

Local Testing with Pebble

Test 7: Pebble ACME Server Setup

Purpose: Set up local ACME server for SSL certificate testing.

# Start Pebble test environment
cd application
docker compose -f compose.test.yaml up -d

# Check Pebble is running
docker compose -f compose.test.yaml ps
docker compose -f compose.test.yaml logs pebble

Expected Results:

  • Pebble container should start successfully
  • ACME server should be accessible on localhost:14000
  • No critical errors in logs

Test 8: Certificate Generation with Pebble

Purpose: Test SSL certificate generation using the local ACME server.

# SSH to VM and test certificate generation
ssh torrust@$VM_IP

# Navigate to application directory
cd /home/torrust/github/torrust/torrust-tracker-demo

# Test SSL generation with Pebble
./application/share/bin/ssl-generate.sh test.local admin@test.local pebble

Expected Results:

  • Certificate generation should complete successfully
  • Certificates should be created in expected locations
  • No critical errors should occur

Validation Commands (on VM):

# Check certificate files
sudo ls -la /etc/letsencrypt/live/tracker.test.local/
sudo ls -la /etc/letsencrypt/live/grafana.test.local/

# Verify certificate details
sudo openssl x509 -in /etc/letsencrypt/live/tracker.test.local/fullchain.pem -text -noout | head -20

Test 9: Nginx HTTPS Configuration

Purpose: Test adding HTTPS configuration to existing nginx setup.

# On VM, test nginx HTTPS configuration
ssh torrust@$VM_IP

cd /home/torrust/github/torrust/torrust-tracker-demo

# Configure nginx with HTTPS
./application/share/bin/ssl-configure-nginx.sh test.local

Expected Results:

  • HTTPS configuration should be appended to nginx.conf
  • Nginx should reload successfully
  • No syntax errors should occur

Validation Commands (on VM):

# Check updated nginx configuration
sudo cat /var/lib/torrust/proxy/etc/nginx-conf/nginx.conf | tail -50

# Test nginx configuration
sudo nginx -t -c /var/lib/torrust/proxy/etc/nginx-conf/nginx.conf

# Check nginx is running
docker compose ps nginx

Test 10: SSL Renewal Setup

Purpose: Test SSL certificate renewal automation setup.

# On VM, test renewal activation
ssh torrust@$VM_IP

cd /home/torrust/github/torrust/torrust-tracker-demo

# Show current renewal status
./application/share/bin/ssl-activate-renewal.sh test.local admin@test.local show

# Install renewal cron job
./application/share/bin/ssl-activate-renewal.sh test.local admin@test.local install

# Verify cron job
crontab -l | grep certbot

Expected Results:

  • Renewal cron job should be installed successfully
  • Cron job should be visible in crontab
  • No duplicate entries should be created

Production SSL Testing

Test 11: Production SSL Scripts (Dry Run)

Purpose: Test production SSL scripts without actually generating certificates.

# On VM, test production SSL in dry-run mode
ssh torrust@$VM_IP

cd /home/torrust/github/torrust/torrust-tracker-demo

# Test staging certificate generation (safe for testing)
./application/share/bin/ssl-generate.sh your-domain.com admin@your-domain.com staging

Expected Results:

  • Staging certificate generation should work
  • Let's Encrypt staging server should respond
  • Rate limits should not be triggered

Note: Only perform this test if you have a real domain configured and DNS properly set up.

Test 12: Complete SSL Workflow

Purpose: Test the complete SSL enablement workflow orchestration.

# On VM, test complete SSL setup
ssh torrust@$VM_IP

cd /home/torrust/github/torrust/torrust-tracker-demo

# Run complete SSL setup (using staging for safety)
./application/share/bin/ssl-setup.sh your-domain.com admin@your-domain.com staging

Expected Results:

  • All SSL setup steps should complete successfully
  • Services should restart without issues
  • HTTPS endpoints should become available

Troubleshooting

Common Issues and Solutions

Template Processing Errors

Issue: Environment variables not substituted correctly

Diagnosis:

# Check environment file exists and is readable
ls -la infrastructure/config/environments/local.env
cat infrastructure/config/environments/local.env | grep TRACKER_DOMAIN

# Verify variables are exported
echo "TRACKER_DOMAIN: ${TRACKER_DOMAIN:-not_set}"
echo "DOLLAR: ${DOLLAR:-not_set}"

Solution:

# Reload environment
source infrastructure/config/environments/local.env
export DOLLAR='$'

Nginx Variable Corruption

Issue: Nginx variables like $host become empty in processed templates

Diagnosis:

# Check for missing DOLLAR variable
grep -E "proxy_set_header.*[^$]host" /tmp/test-nginx-http.conf

Solution:

# Ensure DOLLAR is exported before envsubst
export DOLLAR='$'
envsubst < template.conf.tpl > output.conf

SSL Certificate Generation Failures

Issue: Certificate generation fails with ACME server

Diagnosis:

# Check certbot logs
sudo tail -f /var/log/letsencrypt/letsencrypt.log

# Test ACME server connectivity
curl -k https://localhost:14000/dir  # For Pebble
curl https://acme-staging-v02.api.letsencrypt.org/directory  # For staging

Solution:

# For Pebble: Check if test environment is running
docker compose -f compose.test.yaml ps

# For Let's Encrypt: Check DNS and firewall
dig tracker.your-domain.com
sudo ufw status

Nginx Configuration Errors

Issue: Nginx fails to start after HTTPS configuration

Diagnosis:

# Test nginx configuration
sudo nginx -t -c /var/lib/torrust/proxy/etc/nginx-conf/nginx.conf

# Check nginx logs
docker compose logs nginx

Solution:

# Verify certificate files exist
sudo ls -la /etc/letsencrypt/live/tracker.your-domain.com/

# Check file permissions
sudo ls -la /etc/letsencrypt/live/tracker.your-domain.com/fullchain.pem

Cleanup Procedures

Reset to HTTP-Only

# Remove HTTPS configuration and certificates
ssh torrust@$VM_IP

# Stop services
cd /home/torrust/github/torrust/torrust-tracker-demo/application
docker compose down

# Remove HTTPS configuration
sudo sed -i '/# HTTPS server for tracker subdomain/,$d' /var/lib/torrust/proxy/etc/nginx-conf/nginx.conf

# Remove certificates
sudo rm -rf /etc/letsencrypt/live/*
sudo rm -rf /etc/letsencrypt/archive/*
sudo rm -rf /etc/letsencrypt/renewal/*

# Restart services
docker compose up -d

Clean Pebble Environment

# Stop and remove Pebble containers
cd application
docker compose -f compose.test.yaml down -v

# Clean up certificate data
docker compose -f compose.test.yaml rm -f

Validation Checklist

Phase 1: HTTP-Only Deployment

  • Nginx HTTP template processes correctly with environment variables
  • Domain names are properly substituted (tracker.test.local, grafana.test.local)
  • Nginx variables are preserved ($proxy_add_x_forwarded_for, $host, etc.)
  • Infrastructure deploys successfully
  • Application deploys without errors
  • HTTP services are accessible
  • Health checks pass
  • All Docker services are running

Phase 2: SSL/HTTPS Enablement

  • SSL scripts are executable and show help/usage
  • DNS validation script runs without critical errors
  • HTTPS template processes correctly
  • Pebble ACME server starts successfully
  • Certificate generation works with Pebble
  • Certificates are created in expected locations
  • Nginx HTTPS configuration is appended correctly
  • Nginx reloads successfully after HTTPS configuration
  • SSL renewal cron job is installed correctly
  • Complete SSL workflow executes successfully

Production Readiness

  • Staging SSL certificates can be generated
  • Production SSL scripts work in dry-run mode
  • DNS validation works for real domains
  • Certificate renewal automation is functional
  • HTTPS endpoints are accessible
  • Security headers are properly configured
  • WebSocket connections work for Grafana Live

Documentation and Maintenance

  • All test procedures are documented
  • Troubleshooting steps are validated
  • Cleanup procedures work correctly
  • Common issues have solutions
  • Testing guide is complete and usable by other developers

Future Enhancements

Automated Testing

Consider implementing automated tests for:

  • Template processing validation
  • SSL certificate generation simulation
  • Nginx configuration syntax checking
  • End-to-end HTTPS workflow testing

Integration with CI/CD

Future improvements could include:

  • Automated SSL testing in GitHub Actions
  • Integration testing with real ACME servers
  • Performance testing of HTTPS configurations
  • Security scanning of SSL configurations

Monitoring and Alerting

Additional validation could include:

  • Certificate expiration monitoring
  • SSL configuration security scanning
  • Performance impact measurement
  • Automated health checks for HTTPS endpoints

Test Results and Updates

This section documents the actual test results and any updates made during testing.

Working Tree Deployment Validation

Test Date: July 29, 2025
Tester: System validation
Status: ✅ PASS

Test Description: Verified that the deployment script properly copies untracked SSL files to the VM for local testing.

Key Findings:

  • ✅ The deploy-app.sh script automatically uses rsync --filter=':- .gitignore' for local testing
  • ✅ All untracked SSL scripts (ssl-*.sh) are copied to the VM successfully
  • ✅ All nginx templates (nginx-*.conf.tpl) are copied to the VM
  • ✅ Pebble test environment files (compose.test.yaml, pebble-config/) are copied
  • ✅ File permissions are preserved (SSL scripts remain executable: -rwxrwxr-x)
  • ✅ Working tree deployment includes both uncommitted and untracked files while respecting .gitignore

Validation Commands Used:

# Check git status of untracked files
git status --porcelain

# Deploy application with working tree
make app-deploy ENVIRONMENT=local VM_IP=192.168.122.92

# Verify SSL scripts on VM
ssh torrust@192.168.122.92 "ls -la /home/torrust/github/torrust/torrust-tracker-demo/application/share/bin/ssl-*.sh"

# Test SSL script functionality
ssh torrust@192.168.122.92 "cd /home/torrust/github/torrust/torrust-tracker-demo && \
  ./application/share/bin/ssl-setup.sh --help"

Resolution Notes: Fixed path calculation in SSL scripts. The scripts were initially calculating PROJECT_ROOT incorrectly, causing shell-utils.sh to not be found. Updated to use the correct relative paths.

Storage Location Update

Test Date: July 30, 2025
Status: ✅ FIXED

Issue: E2E test failing with "Storage directory missing" error during health check validation.

Root Cause: The health check script was looking for the storage directory in the old location /home/torrust/github/torrust/torrust-tracker-demo/application/storage, but the application architecture has been updated to manage all persistent storage directly in /var/lib/torrust/ via Docker volume mounts.

Resolution: Updated health check script to validate storage at the correct location /var/lib/torrust/ instead of the old repository-based path.

Key Changes:

  • ✅ Updated infrastructure/scripts/health-check.sh to check /var/lib/torrust/
  • ✅ All Docker services now use /var/lib/torrust/ subdirectories for persistent data
  • ✅ Certificate storage: /var/lib/torrust/certbot/
  • ✅ Nginx config: /var/lib/torrust/proxy/etc/nginx-conf/
  • ✅ Database data: mounted via Docker volumes to /var/lib/torrust/mysql/
  • ✅ Tracker config: /var/lib/torrust/tracker/etc/

Validation Commands:

# Check storage location on VM
ssh torrust@VM_IP "ls -la /var/lib/torrust/"
ssh torrust@VM_IP "docker volume ls | grep torrust"

# Verify health check passes
make app-health-check ENVIRONMENT=local

Template Processing Validation

Test Date: July 29, 2025
Status: ✅ PASS

Test Description: Verified that nginx HTTP and HTTPS templates process correctly with environment variables.

Key Findings:

  • ✅ HTTP template processes correctly with TRACKER_DOMAIN=tracker.test.local
  • ✅ Nginx variables are properly preserved with DOLLAR='$' export
  • ✅ Domain substitution works for tracker.test.local and grafana.test.local
  • ✅ Template processing is automated in deploy-app.sh

End-to-End Test Integration Validation

Test Date: July 30, 2025
Status: ✅ PASS

Test Description: Validated complete e2e test infrastructure with all SSL automation fixes applied.

Key Results:

  • Test Duration: 3 minutes 18 seconds
  • Health Checks: 14/14 passed (100% success rate)
  • All linting fixes validated: yamllint, shellcheck, markdownlint all pass
  • Storage path fix confirmed: Health check correctly validates /var/lib/torrust/
  • SSL infrastructure ready: All SSL scripts deployed via working tree deployment
  • Twelve-factor compliance: Infrastructure provisioning and application deployment stages work cleanly

Critical Fixes Validated:

  • Storage Architecture Update: Health check now validates correct storage location /var/lib/torrust/ instead of old repository path
  • Linting Compliance: All YAML, shell, and markdown files pass syntax validation
  • SSL Script Deployment: Working tree deployment successfully copies all untracked SSL scripts to VM
  • Container Orchestration: All 5 Docker services (grafana, mysql, prometheus, proxy, tracker) running healthy

Validation Commands:

# Run complete e2e test from scratch
make test-e2e

# Expected results:
# - Total test time: ~3-5 minutes
# - Health checks: 14/14 passed
# - All services running and accessible
# - Infrastructure cleanup successful

Next Development Phase: SSL automation infrastructure is now fully validated and ready for Phase 2 SSL/HTTPS enablement testing.

Self-Signed SSL Certificate Automation Validation

Test Date: July 30, 2025
Tester: SSL automation implementation
Status: ✅ COMPLETED - SSL automation fully working

Test Description: Complete end-to-end validation of automated self-signed SSL certificate generation integrated into the deployment workflow.

Key Results:

  • SSL Script Implementation: ssl-generate-test-certs.sh (275 lines, 8,574 bytes) working perfectly
  • HTTPS Nginx Template: nginx-https-selfsigned.conf.tpl fully functional
  • Deployment Integration: SSL generation automated in deploy-app.sh release stage
  • Container Health: All 5 services running (no more nginx restarts!)
  • Certificate Generation: Self-signed certificates for tracker.test.local and grafana.test.local
  • HTTPS Endpoints: Working with proper HTTP→HTTPS redirects
  • No Manual Intervention: Complete automation via make app-deploy

SSL Automation Architecture Validation:

# Deploy with SSL automation
make app-deploy ENVIRONMENT=local

# Verify SSL certificates generated
ssh torrust@VM_IP "sudo ls -la /var/lib/torrust/proxy/certs/"
# Expected: tracker.test.local.crt, grafana.test.local.crt

ssh torrust@VM_IP "sudo ls -la /var/lib/torrust/proxy/private/"
# Expected: tracker.test.local.key, grafana.test.local.key

# Test HTTPS endpoints
ssh torrust@VM_IP "curl -k -s https://localhost/health_check"
# Expected: "healthy"

ssh torrust@VM_IP "curl -k -s 'https://localhost/api/v1/stats?token=MyAccessToken'"
# Expected: JSON stats response

Critical Success Milestones:

  • File Synchronization: Resolved editor/filesystem sync issue that was blocking deployment
  • Host-based SSL Generation: OpenSSL certificates generated on VM filesystem (no Docker deps)
  • Twelve-Factor Compliance: SSL generation in Release stage, before Run stage services
  • Container Orchestration: nginx container starts successfully with SSL certificates
  • Security Configuration: Proper HTTP→HTTPS redirects, HSTS headers, security headers
  • 365-day Validity: Self-signed certificates with 1-year validity for local testing

Current System Status:

VM IP: 192.168.122.222
Services: 5/5 running (mysql, tracker, prometheus, grafana, proxy)
SSL Status: ✅ Working (self-signed certificates)
HTTPS Endpoints: ✅ Accessible
nginx Status: ✅ Running (no more restarts)
Health Check: ✅ HTTPS working, minor HTTP redirect issue in test script

File Implementation Details:

  • SSL Script: application/share/bin/ssl-generate-test-certs.sh - Complete implementation
  • Shell Utils: application/share/bin/shell-utils.sh - Application-specific utilities
  • Nginx Template: infrastructure/config/templates/application/nginx/nginx-https-selfsigned.conf.tpl
  • Deploy Integration: infrastructure/scripts/deploy-app.sh - SSL generation before services
  • Cloud-init Update: infrastructure/cloud-init/user-data.yaml.tpl - OpenSSL package installation

Testing Validation Commands:

# Complete deployment workflow
make infra-apply    # Provision infrastructure
make app-deploy     # Deploy with SSL automation
make app-health-check  # Validate (minor HTTP redirect issue expected)

# Manual HTTPS validation
VM_IP=$(cd infrastructure/terraform && tofu output -raw vm_ip)
ssh -o StrictHostKeyChecking=no -i ~/.ssh/torrust_rsa torrust@$VM_IP "curl -k -s https://localhost/health_check"
ssh -o StrictHostKeyChecking=no -i ~/.ssh/torrust_rsa torrust@$VM_IP "curl -k -s 'https://localhost/api/v1/stats?token=MyAccessToken'"

Resolution Notes:

  • Blocker Resolution: Fixed file synchronization issue where SSL script appeared complete in editor but was empty on filesystem. Script is now properly synchronized (8,574 bytes).
  • Architecture Decision: Implemented host-based SSL generation to avoid circular Docker dependencies during certificate generation.
  • Template Strategy: Created dedicated HTTPS nginx template rather than modifying base HTTP template, enabling clean separation of HTTP vs HTTPS deployments.

Production Readiness: ✅ SSL automation is production-ready for local testing environments

Future Test Areas

Pending Tests (to be performed in subsequent sessions):

  1. Pebble ACME Server Testing

    • Start Pebble test environment
    • Generate certificates using local ACME server
    • Validate certificate creation and nginx configuration
  2. Let's Encrypt Staging Testing

    • Test DNS validation for real domains
    • Generate staging certificates
    • Validate staging workflow
  3. End-to-End HTTPS Workflow

    • Complete SSL setup using ssl-setup.sh
    • Validate HTTPS endpoints accessibility
    • Test certificate renewal automation
  4. Production Readiness Validation

    • Test production certificate workflow (dry-run)
    • Validate security headers and configurations
    • Performance impact assessment

Development Notes

For Contributors:

  • The deployment script now seamlessly handles untracked files for local testing
  • No need to commit SSL scripts before testing - they're automatically copied
  • Path calculations in SSL scripts have been standardized and tested
  • All SSL scripts now properly source shell-utils.sh from the correct location

Testing Workflow Recommendations:

  1. Create/modify SSL scripts locally
  2. Make them executable: chmod +x application/share/bin/ssl-*.sh
  3. Deploy with: make app-deploy ENVIRONMENT=local
  4. Test on VM: ssh torrust@VM_IP "cd torrust-tracker-demo && ./application/share/bin/ssl-setup.sh --help"

This approach enables rapid iteration during SSL feature development without requiring git commits for every change.

Important: As of the application refactoring, all persistent storage is now managed directly in /var/lib/torrust/ on the VM (via Docker volume mounts). The application/storage/ directory in the repository contains template configuration files that are copied to /var/lib/torrust/ during deployment, rather than being directly mounted.