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How to Auto-Renew a Let's Encrypt Certificate

TL;DR:

Let's Encrypt auto-renewal: sudo certbot renew --dry-run — test. Then cron: 0 3 * * * certbot renew --quiet --post-hook "systemctl reload nginx". Let's Encrypt is valid 90 days; certbot renews 30 days before expiry.

Step-by-step guide

  1. Check certificate expiry. Online: /en/ssl. CLI: sudo certbot certificates.
  2. Dry-run renewal. sudo certbot renew --dry-run — tests the renewal without touching the live certificate.
  3. Configure cron for auto-renewal. sudo crontab -e0 3 * * * certbot renew --quiet --post-hook "systemctl reload nginx"
  4. SSL expiry monitoring. Enable Enterno.io SSL monitoring — email/Telegram alert 14 days before expiry if certbot fails for any reason.
  5. Post-renewal verification. After a minute, check curl -sI https://example.com — new Not-After expected. Or Ctrl+Shift+R in the browser.

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CertificateExpiry, issuer, domains (SAN)
ChainIntermediate and root CA validation
TLS ProtocolTLS version and cipher suite
VulnerabilitiesHeartbleed, POODLE, weak ciphers

Why teams trust us

TLS 1.3
supported
Full
CA chain check
<2s
result
30/14/7
days-to-expiry alerts

How it works

1

Enter domain

2

TLS chain verified

3

Expiry date & vulnerabilities

What Does the SSL Check Cover?

SSL/TLS is the encryption protocol that protects data between the browser and server. Our tool analyzes the certificate, chain of trust, TLS version, and knownvulnerabilities.

Certificate Details

Issuer, validity period, signature algorithm, covered domains (SAN), and validation type (DV/OV/EV).

Chain of Trust

Full chain verification: from leaf certificate through intermediates to root CA.

TLS Analysis

Protocol version (TLS 1.2/1.3), cipher suites, Perfect Forward Secrecy (PFS) support.

Expiry Alerts

Set up a monitor — get Telegram and email alerts 30/14/7 days before expiration.

DV vs OV vs EV Certificates

DV (Domain Validation)
  • Confirms domain ownership only
  • Issued in minutes automatically
  • Free via Let's Encrypt
  • Suitable for most websites
  • Most common certificate type
OV / EV
  • Organization (OV) or Extended Validation (EV)
  • Issued in 1-5 business days
  • Costs $50 to $500/year
  • For finance, e-commerce, government sites
  • Increases user trust

Who uses this

DevOps

SSL certificate monitoring

Security

TLS config audit

SEO

HTTPS as ranking factor

E-commerce

customer trust

Common Mistakes

Expired certificateBrowsers block sites with expired SSL. Set up auto-renewal or monitoring.
Incomplete certificate chainWithout intermediate CA, some browsers and bots cannot verify the certificate.
Mixed content on HTTPS siteHTTP resources on an HTTPS page — the browser lock icon disappears, reducing trust.
Using TLS 1.0/1.1Legacy TLS versions have known vulnerabilities. Use TLS 1.2+ or 1.3.
Domain mismatch in certificateThe certificate must cover all site domains, including www and subdomains.

Best Practices

Set up auto-renewalLet's Encrypt + certbot with cron — certificate renews automatically every 60-90 days.
Enable HSTSStrict-Transport-Security header forces browsers to always use HTTPS.
Use TLS 1.3TLS 1.3 is faster (1-RTT handshake) and safer — legacy ciphers removed.
Monitor expiration datesCreate a monitor on Enterno.io — get notified well before expiration.
Verify chain after renewalAfter certificate renewal, confirm that intermediate certificates are installed.

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