I wish Nginx would improve their developer experience. Their deployment patterns and configuration are horrid compared to Caddy which is amazing to use.

Caddy has a lot of great features, but (at least as of last year) Nginx has the edge on documentation. Caddy’s docs were almost useless. Hopefully they’ve improved since I last used it.

The docs were brilliant for v1, it wouldn't surprise me if they were the spec for a great user experience and the code came second.

Despite v2 supporting a very similar config file, the documentation doesn't emphasise that and tries to steer you towards its API, confusing JSON config syntax etc.

It's still a very good web server for very few lines of config, but I don't relish trying to learn something new from its docs like I used to.

I agree with this, v1 was an excellent user experience, I actually ran it on my servers for way too long. There was also the Wedge fork which might have helped with the EOL but sadly it didn't go anywhere: https://github.com/WedgeServer/wedge

> Despite v2 supporting a very similar config file, the documentation doesn't emphasise that and tries to steer you towards its API, confusing JSON config syntax etc.

Others responded to this a bit more, but while I agree that different config types are a confusing experience, at the same time I appreciate that they support something like that in the first place. I might not use it often, but it's nice that you can.