PlannedNetwork & voice

TLS and certificate management

Chains, names, renewal and the expiry that takes a service down on a Sunday.

LevelPractitioner
Material3 modules, 9 lessons
Reading time1 h 33 m
StatusPlanned — not open

This course is not available yet

It is planned and the outline below is a first draft, so it may yet change. There is no enrolment and no date — when it is ready it will be on this page. Several of the lessons are built around tools on this site that already work, so you can practise the measurements today.

If you need this capability now rather than later, Cybersecurity services is the service that covers it, or talk to us.

Who it is for

Whoever gets the call when a certificate expires, which is usually whoever is on call.

Practitioner. For people who administer these systems day to day.

Assumed beforehand:

  • Basic familiarity with DNS and with a web server or load balancer

What you will be able to do

  • Read a certificate and a signing request without guessing at the fields
  • Explain why browsers ignore the common name and match only the SAN
  • Diagnose an incomplete chain, which fails on some clients and not others
  • Automate renewal so expiry stops being an event

Outline

3 modules, 9 lessons, 1 h 33 m of material. The times are the sum of the lessons rather than a round figure.

01What a certificate asserts

A signed statement binding a key to names, for a period, for particular uses.

Keys, names, validity, constraints12 m

The four fields that matter and the ways each goes wrong.

Why the common name is decorative8 m

The SAN extension, and the certificate that covers nothing.

Wildcards, and exactly what they cover9 m

One label, and the key that then protects every host under the name.

02Chains

The failure that works in your browser and not on a customer’s server.

Leaf, intermediate, root10 m

What the server must send, and what it must not.

The incomplete chain12 m

Why some clients fetch the missing link and others simply fail.

Expiry, revocation and short lifetimes10 m

Why validity periods keep shrinking and revocation never worked.

03Operations

Renewal is a process problem wearing a cryptography costume.

Automating issuance12 m

ACME, the challenge types, and where automation usually gets stuck.

Inventory and monitoring10 m

Knowing what you have before it expires, including the ones nobody owns.

Private CAs, and when they are the answer10 m

Internal services, device fleets, and the trust store problem.

Format. Written lessons with exercises using this site’s certificate decoder and SSL checker. Delivery mechanism is not built yet.

Would you rather we just did it?

This course exists because the work behind it is work we do. If you need the result rather than the skill, cybersecurity services is the service that covers it.