Certificate Management

Introduction

TLS certificate management is a critical operational responsibility. Expired certificates cause service outages, security warnings, and loss of user trust. Modern certificate management leverages the ACME protocol and Let's Encrypt to automate issuance and renewal at scale.

Let's Encrypt

Let's Encrypt is a free, automated, and open certificate authority (CA) that provides DV certificates trusted by all major browsers.

Install Certbot (Let's Encrypt client)

sudo apt install certbot python3-certbot-nginx

Obtain certificate with webroot authentication

sudo certbot certonly --webroot \

-w /var/www/example.com -d example.com \

-w /var/www/api.example.com -d api.example.com \

\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\--email admin@example.com \

\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\--agree-tos \

\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\--non-interactive

Obtain certificate with DNS challenge (for wildcards)

sudo certbot certonly --manual \

\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\\--preferred-challenges dns \

-d example.com -d *.example.com

ACME Protocol

The Automated Certificate Management Environment (ACME) protocol automates certificate issuance, renewal, and revocation.

import josepy as jose

from acme import client, messages

from cryptography import x509

from cryptography.hazmat.primitives import hashes

class ACMEClient:

def init(self, directory_url, email):

self.directory_url = directory_url

self.email = email

self.net = client.ClientNetwork(

jose.JWKRSA(key=rsa_private_key),

user_agent="my-acme-client/1.0"

)

self.directory = messages.Directory.from_json(

self.net.get(directory_url).json()

)

self.acme = client.ClientV2(self.directory, self.net)

def register_account(self):

"""Register ACME account with Let's Encrypt."""

terms = self.directory.meta.terms_of_service

registration = self.acme.new_account(

messages.NewRegistration(

key=self.net.key,

terms_of_service_agreed=True,

contact=[f"mailto:{self.email}"]

)

)

return registration

def request_certificate(self, domain, csr_pem):

"""Request certificate issuance."""

Create authorization

order = self.acme.new_order(csr_pem)

Complete challenges for each identifier

for auth in order.authorizations:

HTTP-01 or DNS-01 challenge

challenge = auth.body.challenges[0]

self.respond_challenge(challenge)

Finalize order

order = self.acme.finalize_order(order, csr_pem)

return order.fullchain_pem

Automated Renewal

Certificate renewal should be fully automated with monitoring and alerting.

Certbot systemd timer for automatic renewal

/etc/systemd/system/certbot-renewal.service

[Unit]

Description=Certbot Renewal

[Service]

Type=oneshot

ExecStart=/usr/bin/certbot renew --quiet --pre-hook "systemctl reload nginx"

ExecStartPost=/usr/bin/systemctl reload nginx

/etc/systemd/system/certbot-renewal.timer

[Unit]

Description=Run certbot renewal twice daily

[Timer]

OnCalendar=- -* 00:00,12:00

RandomizedDelaySec=3600

Persistent=true

[Install]

WantedBy=timers.target

Enable timer

sudo systemctl enable certbot-renewal.timer

sudo systemctl start certbot-renewal.timer

Test renewal process

sudo certbot renew --dry-run

Certificate Monitoring

Monitor certificate expiration to catch renewal failures before they cause outages.

import ssl

import datetime

import socket

from typing import Dict, List

class CertificateMonitor:

def init(self, warning_days: int = 30, critical_days: int = 7):

self.warning_days = warning_days

self.critical_days = critical_days

def check_certificate(self, hostname: str, port: int = 443) -> Dict:

context = ssl.create_default_context()

context.check_hostname = True

with socket.create_connection((hostname, port), timeout=10) as sock:

with context.wrap_socket(sock, server_hostname=hostname) as ssock:

cert = ssock.getpeercert()

Parse expiration

expires = datetime.datetime.strptime(

cert['notAfter'], '%b %d %H:%M:%S %Y %Z'

)

remaining = (expires - datetime.datetime.utcnow()).days

Check issuer

issuer = dict(x[0] for x in cert['issuer'])

Check SANs

sans = [san[1] for san in cert.get('subjectAltName', [])]

return {

'hostname': hostname,

'subject': cert['subject'],

'issuer': issuer.get('organizationName', 'Unknown'),

'expires': expires.isoformat(),

'remaining_days': remaining,

'sans': sans,

'serial': cert.get('serialNumber'),

'status': self._get_status(remaining),

}

def _get_status(self, remaining_days: int) -> str:

if remaining_days <= 0:

return 'EXPIRED'

elif remaining_days <= self.critical_days:

return 'CRITICAL'

elif remaining_days <= self.warning_days:

return 'WARNING'

return 'OK'

def monitor_domains(self, domains: List[str]) -> List[Dict]:

results = []

for domain in domains:

try:

result = self.check_certificate(domain)

results.append(result)

if result['status'] in ('CRITICAL', 'EXPIRED'):

self.alert(result)

except Exception as e:

results.append({

'hostname': domain,

'status': 'ERROR',

'error': str(e)

})

return results

OpenSSL-based certificate check

echo | openssl s_client -connect example.com:443 -servername example.com 2>/dev/null | \

openssl x509 -noout -enddate -subject -issuer

Mass certificate check

for domain in $(cat domains.txt); do

expires=$(echo | openssl s_client -connect $domain:443 -servername $domain 2>/dev/null | \

openssl x509 -noout -enddate | cut -d= -f2)

remaining=$(( ($(date -d "$expires" +%s) - $(date +%s)) / 86400 ))

echo "$domain: expires in $remaining days ($expires)"

done

Certificate Revocation

Check OCSP status

openssl ocsp -issuer chain.pem -cert cert.pem \

-url $(openssl x509 -in cert.pem -noout -ocsp_uri) \

-header "Host" $(openssl x509 -in cert.pem -noout -ocsp_uri | cut -d/ -f3) \

-CAfile root.pem

CRL check

curl -O http://crl.example.com/intermediate.crl

openssl crl -in intermediate.crl -noout -text | grep -A1 "Serial Number"

Conclusion

Modern certificate management means automation. Use Let's Encrypt with Certbot for domain-validated certificates, implement ACME for custom automation, set up systemd timers for renewal, and deploy monitoring that alerts days or weeks before expiration. Never rely on manual renewal processes — they fail under pressure and at scale.