Implementing TLS

Purpose

Implement Transport Layer Security (TLS) for encrypting network communications and authenticating services. Generate certificates, automate certificate lifecycle management with Let's Encrypt or internal CAs, configure TLS 1.3, implement mutual TLS for service authentication, and debug common certificate issues.

When to Use This Skill

Trigger this skill when:

• Setting up HTTPS for web applications or APIs
• Securing service-to-service communication in microservices
• Implementing mutual TLS (mTLS) for zero-trust networks
• Generating certificates for development or production
• Automating certificate renewal and rotation
• Debugging certificate validation errors
• Configuring TLS termination at load balancers
• Setting up internal PKI for corporate networks

Quick Start

For Development (Local HTTPS)

Use mkcert for trusted local certificates:

# Install mkcert
brew install mkcert  # macOS
# sudo apt install mkcert  # Linux

# Install local CA
mkcert -install

# Generate certificate
mkcert example.com localhost 127.0.0.1
# Creates: example.com+2.pem and example.com+2-key.pem

For Production (Public HTTPS)

Kubernetes with cert-manager:

# Install cert-manager
helm install cert-manager jetstack/cert-manager \
  --namespace cert-manager --create-namespace \
  --set installCRDs=true

# Create Let's Encrypt issuer
kubectl apply -f - <<EOF
apiVersion: cert-manager.io/v1
kind: ClusterIssuer
metadata:
  name: letsencrypt-prod
spec:
  acme:
    server: https://acme-v02.api.letsencrypt.org/directory
    email: admin@example.com
    privateKeySecretRef:
      name: letsencrypt-prod-key
    solvers:
    - http01:
        ingress:
          class: nginx
EOF

Traditional servers with Certbot:

# Install certbot
sudo apt install certbot

# Obtain certificate
sudo certbot certonly --standalone -d example.com -d www.example.com
# Certificates saved to /etc/letsencrypt/live/example.com/

For Internal Services (Internal PKI)

Generate internal CA with CFSSL:

# Install CFSSL
brew install cfssl  # macOS

# Create CA
cfssl genkey -initca ca-csr.json | cfssljson -bare ca

# Generate server certificate
cfssl gencert -ca=ca.pem -ca-key=ca-key.pem \
  -config=ca-config.json -profile=server \
  server-csr.json | cfssljson -bare server

See examples/cfssl-ca/ for complete configuration files.

TLS 1.3 Configuration Best Practices

Protocol Versions

Enable TLS 1.3 and 1.2 only:

# Nginx
ssl_protocols TLSv1.3 TLSv1.2;
ssl_prefer_server_ciphers off;  # Let client choose

Disable obsolete protocols: SSLv3, TLS 1.0, TLS 1.1.

Cipher Suites

TLS 1.3 (5 cipher suites):

TLS_AES_256_GCM_SHA384           # Recommended
TLS_CHACHA20_POLY1305_SHA256     # Mobile-optimized
TLS_AES_128_GCM_SHA256           # Performance

TLS 1.2 fallback:

ssl_ciphers 'ECDHE-RSA-AES256-GCM-SHA384:ECDHE-RSA-AES128-GCM-SHA256:ECDHE-RSA-CHACHA20-POLY1305';

Security Features

• Perfect Forward Secrecy (PFS): Use ephemeral key exchanges (ECDHE)
• OCSP Stapling: Enable for performance and privacy
• HSTS: Force HTTPS with Strict-Transport-Security header
• Disable compression: Prevent CRIME attacks

For detailed TLS 1.3 configuration, see references/tls13-best-practices.md.

Decision Framework

Certificate Type Selection

Need TLS certificate?
│
├─ Public-facing (internet users)?
│  │
│  ├─ Single domain → Let's Encrypt with HTTP-01
│  │  Tools: certbot, cert-manager
│  │  Challenge: HTTP verification
│  │
│  └─ Multiple subdomains → Let's Encrypt with DNS-01
│     Tools: certbot with DNS plugin, cert-manager
│     Challenge: DNS TXT records
│     Supports: Wildcard certificates (*.example.com)
│
└─ Internal (corporate network)?
   │
   ├─ Development → mkcert or self-signed
   │  Tools: mkcert (trusted), openssl (basic)
   │  No automation needed
   │
   └─ Production → Internal CA
      │
      ├─ Small scale (<10 services) → CFSSL
      │  Manual management acceptable
      │
      └─ Large scale (100+ services) → Vault PKI or cert-manager
         Dynamic secrets, automatic rotation

Automation Tool Selection

Environment?
│
├─ Kubernetes → cert-manager
│  Native CRDs, Ingress integration
│  Supports: Let's Encrypt, Vault, CA, self-signed
│
├─ Traditional servers (VMs) → Certbot (public) or CFSSL (internal)
│  Plugins: nginx, apache, DNS providers
│  Automated renewal via cron/systemd
│
├─ Microservices (any platform) → HashiCorp Vault PKI
│  Dynamic secrets, short-lived certs
│  API-driven, service mesh integration
│
└─ Developer workstation → mkcert
   Trusted by browser automatically

Standard TLS vs Mutual TLS (mTLS)

Use Standard TLS (server-only authentication) when:

• Public websites (users trust server)
• APIs with bearer tokens (separate auth layer)
• Services behind API gateway
• Simple architectures (<5 services)

Use Mutual TLS (both authenticate) when:

• Service-to-service in microservices
• High security requirements (financial, healthcare)
• Machine-to-machine APIs
• Zero-trust networks
• No shared network trust

See references/mtls-guide.md for mTLS implementation patterns.

Common Workflows

Generate Self-Signed Certificate

Quick generation with SANs:

# Create OpenSSL config
cat > san.cnf <<EOF
[req]
default_bits = 2048
prompt = no
default_md = sha256
distinguished_name = dn
req_extensions = v3_req

[dn]
CN = example.com

[v3_req]
subjectAltName = @alt_names

[alt_names]
DNS.1 = example.com
DNS.2 = www.example.com
DNS.3 = api.example.com
IP.1 = 192.168.1.100
EOF

# Generate key and certificate
openssl req -x509 -newkey rsa:2048 -nodes \
  -keyout server-key.pem -out server-cert.pem \
  -days 365 -config san.cnf -extensions v3_req

# Verify SANs
openssl x509 -in server-cert.pem -noout -text | grep -A 3 "Subject Alternative Name"

For detailed examples including CFSSL and mkcert, see references/certificate-generation.md and examples/self-signed/.

Setup Let's Encrypt Automation

With Certbot (traditional servers):

# Standalone mode (port 80 must be free)
sudo certbot certonly --standalone -d example.com -d www.example.com

# Webroot mode (no service interruption)
sudo certbot certonly --webroot -w /var/www/html -d example.com

# DNS challenge (wildcard support)
sudo certbot certonly --manual --preferred-challenges dns \
  -d example.com -d "*.example.com"

# Test renewal
sudo certbot renew --dry-run

With cert-manager (Kubernetes):

# Ingress with automatic certificate
apiVersion: networking.k8s.io/v1
kind: Ingress
metadata:
  name: example-ingress
  annotations:
    cert-manager.io/cluster-issuer: "letsencrypt-prod"
spec:
  tls:
  - hosts:
    - example.com
    secretName: example-com-tls
  rules:
  - host: example.com
    http:
      paths:
      - path: /
        pathType: Prefix
        backend:
          service:
            name: web-service
            port:
              number: 80

See references/automation-patterns.md for complete automation guides.

Configure Mutual TLS (mTLS)

Server configuration (Nginx):

server {
    listen 443 ssl;
    server_name api.example.com;

    # Server certificate
    ssl_certificate /etc/ssl/certs/server.crt;
    ssl_certificate_key /etc/ssl/private/server.key;

    # CA to verify client certificates
    ssl_client_certificate /etc/ssl/certs/ca.crt;
    ssl_verify_client on;
    ssl_verify_depth 2;

    # TLS 1.3
    ssl_protocols TLSv1.3;

    location / {
        proxy_pass http://backend;
        # Pass client cert info to backend
        proxy_set_header X-SSL-Client-Cert $ssl_client_cert;
        proxy_set_header X-SSL-Client-S-DN $ssl_client_s_dn;
    }
}

Client request with certificate:

curl https://api.example.com/endpoint \
  --cert client.crt \
  --key client.key \
  --cacert ca.crt

See references/mtls-guide.md and