Running an HTTPS website with Let's Encrypt is increasingly becoming a built-in server feature.
For example, Traefik (a reverse proxy for web services) has this functionality in its default feature set!
miniblog.
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Implementation chicken:
When there's an obvious feature gap in an ecosystem and everyone is waiting for someone else to write it.
I see this most frequently with OSS toolchains. Basic functionality in new programming languages is another common scenario.
Caddy is really growing on me. It's nice having a web proxy that includes letsencrypt functionality without any additional configuration.
I've tended to use nginx with a separate letsencrypt setup for projects before, and it's much more awkward.
Individuals and interactions over processes and tools => Competence trumps process
Working software over comprehensive documentation => Minimize time from program launch to deployment of simplest useful functionality
I really like the DoD's phrasings of classic agile maxims: