OpenSSL

Original source / Raw SKILL.md

---
name: OpenSSL
description: Expert guidance for OpenSSL operations including certificate generation, key management, CSR creation, certificate verification, encryption, and PKI operations. Use this when working with SSL/TLS certificates, cryptographic keys, or PKI infrastructure.
---

# OpenSSL

Expert assistance with OpenSSL cryptographic operations and PKI management.

## Key Generation

### RSA Keys
```bash
# Generate RSA private key (2048-bit)
openssl genrsa -out private.key 2048

# Generate RSA private key (4096-bit, more secure)
openssl genrsa -out private.key 4096

# Generate encrypted RSA private key
openssl genrsa -aes256 -out private.key 4096

# Extract public key from private key
openssl rsa -in private.key -pubout -out public.key

# Remove passphrase from encrypted key
openssl rsa -in encrypted.key -out decrypted.key
```

### EC (Elliptic Curve) Keys
```bash
# List available curves
openssl ecparam -list_curves

# Generate EC private key (P-256)
openssl ecparam -name prime256v1 -genkey -noout -out ec-private.key

# Generate EC private key (P-384, more secure)
openssl ecparam -name secp384r1 -genkey -noout -out ec-private.key

# Extract public key
openssl ec -in ec-private.key -pubout -out ec-public.key
```

## Certificate Signing Requests (CSR)

### Create CSR
```bash
# Create CSR from existing private key
openssl req -new -key private.key -out request.csr

# Create CSR with inline subject
openssl req -new -key private.key -out request.csr \
  -subj "/C=US/ST=State/L=City/O=Organization/CN=example.com"

# Generate private key and CSR in one command
openssl req -newkey rsa:2048 -nodes -keyout private.key -out request.csr

# Create CSR with SAN (Subject Alternative Names)
openssl req -new -key private.key -out request.csr -config san.cnf
```

### SAN Configuration File (san.cnf)
```ini
[req]
distinguished_name = req_distinguished_name
req_extensions = v3_req

[req_distinguished_name]
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 = 192.168.1.1
```

### View CSR
```bash
# Display CSR details
openssl req -in request.csr -noout -text

# Verify CSR signature
openssl req -in request.csr -noout -verify
```

## Self-Signed Certificates

### Create Self-Signed Certificate
```bash
# Generate self-signed certificate (1 year validity)
openssl req -x509 -newkey rsa:4096 -keyout key.pem -out cert.pem -days 365

# Generate self-signed certificate without passphrase
openssl req -x509 -newkey rsa:4096 -nodes -keyout key.pem -out cert.pem -days 365

# From existing key
openssl req -x509 -key private.key -out cert.pem -days 365

# With specific subject
openssl req -x509 -newkey rsa:4096 -nodes -keyout key.pem -out cert.pem -days 365 \
  -subj "/C=US/ST=State/L=City/O=Org/CN=example.com"
```

## Certificate Authority (CA) Operations

### Create Root CA
```bash
# Generate CA private key
openssl genrsa -aes256 -out ca-key.pem 4096

# Create CA certificate
openssl req -x509 -new -nodes -key ca-key.pem -sha256 -days 3650 \
  -out ca-cert.pem -subj "/C=US/O=MyOrg/CN=MyOrg Root CA"
```

### Sign Certificate with CA
```bash
# Sign CSR with CA
openssl x509 -req -in request.csr -CA ca-cert.pem -CAkey ca-key.pem \
  -CAcreateserial -out cert.pem -days 365 -sha256

# Sign with extensions (SAN)
openssl x509 -req -in request.csr -CA ca-cert.pem -CAkey ca-key.pem \
  -CAcreateserial -out cert.pem -days 365 -sha256 -extensions v3_req -extfile san.cnf
```

### Create Intermediate CA
```bash
# Generate intermediate CA key
openssl genrsa -aes256 -out intermediate-key.pem 4096

# Create intermediate CSR
openssl req -new -key intermediate-key.pem -out intermediate.csr

# Sign intermediate certificate with root CA
openssl x509 -req -in intermediate.csr -CA ca-cert.pem -CAkey ca-key.pem \
  -CAcreateserial -out intermediate-cert.pem -days 1825 -sha256

# Create certificate chain
cat intermediate-cert.pem ca-cert.pem > chain.pem
```

## Certificate Inspection & Verification

### View Certificate Details
```bash
# Display certificate details
openssl x509 -in cert.pem -noout -text

# Show specific fields
openssl x509 -in cert.pem -noout -subject
openssl x509 -in cert.pem -noout -issuer
openssl x509 -in cert.pem -noout -dates
openssl x509 -in cert.pem -noout -serial
openssl x509 -in cert.pem -noout -fingerprint

# Check expiration
openssl x509 -in cert.pem -noout -enddate

# Show in human-readable format
openssl x509 -in cert.pem -text -noout
```

### Verify Certificates
```bash
# Verify certificate against CA
openssl verify -CAfile ca-cert.pem cert.pem

# Verify certificate chain
openssl verify -CAfile ca-cert.pem -untrusted intermediate-cert.pem cert.pem

# Check if certificate and key match
openssl x509 -noout -modulus -in cert.pem | openssl md5
openssl rsa -noout -modulus -in private.key | openssl md5
```

### Test SSL/TLS Connection
```bash
# Connect to server and show certificate
openssl s_client -connect example.com:443 -showcerts

# Test specific protocol
openssl s_client -connect example.com:443 -tls1_2
openssl s_client -connect example.com:443 -tls1_3

# Test with SNI
openssl s_client -connect example.com:443 -servername example.com

# Check certificate expiration remotely
echo | openssl s_client -connect example.com:443 2>/dev/null | \
  openssl x509 -noout -dates
```

## Format Conversion

### PEM ↔ DER
```bash
# PEM to DER
openssl x509 -in cert.pem -outform DER -out cert.der

# DER to PEM
openssl x509 -in cert.der -inform DER -out cert.pem -outform PEM
```

### PKCS#12 (PFX)
```bash
# Create PKCS#12 bundle (certificate + private key)
openssl pkcs12 -export -out cert.pfx -inkey private.key -in cert.pem

# Include certificate chain
openssl pkcs12 -export -out cert.pfx -inkey private.key -in cert.pem -certfile chain.pem

# Extract from PKCS#12
openssl pkcs12 -in cert.pfx -out cert-and-key.pem -nodes

# Extract only certificate
openssl pkcs12 -in cert.pfx -clcerts -nokeys -out cert.pem

# Extract only private key
openssl pkcs12 -in cert.pfx -nocerts -nodes -out private.key
```

### PKCS#7
```bash
# Convert PEM to PKCS#7
openssl crl2pkcs7 -nocrl -certfile cert.pem -out cert.p7b

# Convert PKCS#7 to PEM
openssl pkcs7 -print_certs -in cert.p7b -out cert.pem
```

## Encryption & Decryption

### Symmetric Encryption
```bash
# Encrypt file with AES-256
openssl enc -aes-256-cbc -salt -in file.txt -out file.enc

# Decrypt file
openssl enc -aes-256-cbc -d -in file.enc -out file.txt

# Encrypt with password from file
openssl enc -aes-256-cbc -salt -in file.txt -out file.enc -pass file:password.txt

# Base64 encode encrypted output
openssl enc -aes-256-cbc -salt -in file.txt -out file.enc -a
```

### Asymmetric Encryption
```bash
# Encrypt with public key
openssl rsautl -encrypt -pubin -inkey public.key -in file.txt -out file.enc

# Decrypt with private key
openssl rsautl -decrypt -inkey private.key -in file.enc -out file.txt
```

## Hashing & Digests

```bash
# Generate hash
openssl dgst -sha256 file.txt
openssl dgst -sha512 file.txt
openssl dgst -md5 file.txt

# Create signature
openssl dgst -sha256 -sign private.key -out signature.bin file.txt

# Verify signature
openssl dgst -sha256 -verify public.key -signature signature.bin file.txt

# HMAC
openssl dgst -sha256 -hmac "secret-key" file.txt
```

## Certificate Revocation

### Create Certificate Revocation List (CRL)
```bash
# Create CRL configuration (crl.cnf)
# [ca section with database and crl settings needed]

# Generate CRL
openssl ca -gencrl -config crl.cnf -out crl.pem

# View CRL
openssl crl -in crl.pem -text -noout

# Verify certificate against CRL
openssl verify -crl_check -CRLfile crl.pem -CAfile ca-cert.pem cert.pem
```

### OCSP (Online Certificate Status Protocol)
```bash
# Start OCSP responder
openssl ocsp -port 8080 -index index.txt -CA ca-cert.pem -rkey ca-key.pem -rsigner ca-cert.pem

# Query OCSP responder
openssl ocsp -issuer ca-cert.pem -cert cert.pem -url http://ocsp.example.com:8080
```

## Common PKI Workflows

### Complete Certificate Workflow
```bash
# 1. Generate private key
openssl genrsa -out server.key 4096

# 2. Create CSR
openssl req -new -key server.key -out server.csr \
  -subj "/C=US/ST=CA/L=SF/O=MyOrg/CN=example.com"

# 3. Sign with CA
openssl x509 -req -in server.csr -CA ca-cert.pem -CAkey ca-key.pem \
  -CAcreateserial -out server.crt -days 365 -sha256

# 4. Verify
openssl verify -CAfile ca-cert.pem server.crt

# 5. Test locally
openssl s_server -cert server.crt -key server.key -accept 8443
```

## Best Practices

1. **Key Size**: Use at least 2048-bit RSA or 256-bit EC keys
2. **Hash Algorithm**: Use SHA-256 or stronger (avoid MD5, SHA-1)
3. **Validity Period**: Certificates should be valid for ≤ 398 days (current CA/Browser Forum baseline)
4. **Private Key Protection**: Always encrypt private keys with strong passphrases
5. **SAN**: Always include Subject Alternative Names, even for single domain
6. **Key Backup**: Securely backup private keys and CA certificates
7. **Certificate Chain**: Always provide complete certificate chain
8. **Regular Rotation**: Rotate certificates before expiration

## Security Notes

- **Never share private keys** - They should remain on the server
- **Use strong passphrases** for encrypted keys (16+ characters)
- **Protect CA keys** with HSM or secure key storage
- **Monitor expiration** - Set up alerts 30 days before expiry
- **Revoke compromised certificates** immediately
- **Use Certificate Transparency** for public certificates