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Your SSL Certificate Will Expire and You Will Forget

Auto-renewal is supposed to handle this. But auto-renewal fails more often than you think. Here's why SSL expiry is still a problem in 2026.

James Wolf

James Wolf

Founder @ SlyDuck

December 31, 2025
SSL certificate expiring

The Most Embarrassing Outage

You've seen it. The browser warning page: "Your connection is not private." Maybe on a competitor's site. Maybe... on your own site.

SSL certificate expiration is the most preventable, most embarrassing outage you can have.

"But I Have Auto-Renewal!"

Famous last words. Here's why auto-renewal fails:

DNS Changes

You moved to Cloudflare but didn't update the certificate validation. Auto-renewal can't verify domain ownership.

Payment Issues

The credit card on your domain registrar expired. Renewal attempted, payment failed, certificate dies.

Provider Outages

Let's Encrypt has rate limits. Cloudflare has incidents. Even the best providers have bad days.

Configuration Drift

That server you set up two years ago? The renewal script is still pointing to the old domain.

Why This Matters

Instant Trust Destruction

Users don't understand SSL warnings. They just see: "This site is dangerous."

SEO Damage

Google downgrades sites with SSL issues. One day of expired certificate can affect your rankings for weeks.

Form Submission Failures

Modern browsers block form submissions to non-HTTPS sites. Your contact form, signup flow, payment page—all broken.

The Real Fix: Monitor It

Auto-renewal is your first line of defense. But it needs backup.

14-Day Warning

Know about expiration two weeks out. That's enough time to investigate and fix.

7-Day Warning

Final reminder. If you're seeing this, something went wrong with auto-renewal.

1-Day Warning

Emergency mode. You should be manually renewing immediately.

The Bottom Line

SSL certificate expiry is boring and preventable. That's exactly why it catches people off guard.

Set up monitoring. Get alerts. Your users will never know how close they came to seeing "Your connection is not private."

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SlyDuck monitors SSL certificate expiry across all your projects. Get alerts at 14, 7, and 1 day before expiration. Never get surprised again.

Never forget SSL again

SlyDuck monitors SSL expiry across all your projects. Get alerts at 30, 14, and 7 days before the scary browser warning shows up.

Monitor Your SSL Certificates
James Wolf

James Wolf

Founder @ SlyDuck

Building SlyDuck: the growth dashboard for vibe coders. Builder, leader, Dad, creator.

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