8

TLS CERTIFICATES

The Definitive Guide

8 chapters Last updated 21 September 2026 Free to read, no account

Certificates used to expire because somebody forgot. Now they expire because a job stopped running, and the job is on a server nobody currently employed configured.

Automation removed most certificate failures and made the remaining ones considerably harder to see, including one that works perfectly in your own browser and fails for everyone else.

This guide covers how TLS actually works, what shortened lifetimes changed, and how to find where your renewal runs before it stops.

In this guide you will learn:

  • What actually happens during a TLS handshake
  • Why lifetimes keep shortening and what it means operationally
  • How to find where your renewal runs when nobody remembers
  • Why an incomplete chain is invisible to the person checking
  • What CAA declares and why most domains do not have it
  • How to test a certificate properly, from outside

Contents

1

What a certificate actually proves

Identity, trust chains, and the root store.

2

The handshake

What happens between request and page, step by step.

3

Lifetimes and automation

Ninety days, ACME, and the new failure mode.

4

Chains, and the failure you cannot see

Why it works for you and breaks for a visitor.

5

Trust failures

The four causes, and what each one needs.

6

Controlling issuance

CAA, and who can currently issue for your domain.

7

Testing properly

From a machine that has never visited your site.

8

Keeping the lineage

Every certificate ever issued is public. Use it.

Chapter 1

What a certificate actually proves

Identity, trust chains, and the root store.

What a certificate actually proves

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Chapter 2

The handshake

What happens between request and page, step by step.

The handshake

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Chapter 3

Lifetimes and automation

Ninety days, ACME, and the new failure mode.

Lifetimes and automation

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Chapter 4

Chains, and the failure you cannot see

Why it works for you and breaks for a visitor.

Chains, and the failure you cannot see

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Chapter 5

Trust failures

The four causes, and what each one needs.

Trust failures

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Chapter 6

Controlling issuance

CAA, and who can currently issue for your domain.

Controlling issuance

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Chapter 7

Testing properly

From a machine that has never visited your site.

Testing properly

This chapter is not written yet. Drop the prose into guide-bodies/<body>.html and rebuild.

Chapter 8

Keeping the lineage

Every certificate ever issued is public. Use it.

Keeping the lineage

This chapter is not written yet. Drop the prose into guide-bodies/<body>.html and rebuild.

Check yours

See where your own domain stands.

Everything in this guide, checked on your domain in about ten seconds. Free, no account, every finding shown in full.