My lab
Keeping Track
TLDR: Do what works for you, but keep track of your stuff. Consistently.
Eldritch
Tool
Renovate
TLDR: Renovate is a great tool for automating package and container updates.
SSL
A Certifiable Hiccup
TLDR: If your automation and infra are not monitored, you won't see it fail.
SSL
Automating SSL
TLDR: Automating your cert renewal isn't hard but you might need to get your mitts muddy.