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What surprising me the most is LiteSpeed is now somewhat unknown web server. Time flies.
I'd never heard until Life speed until today. I wonder if it's one or a few major players using it?
I heard its name frequently around the time before nginx came to its fame. Maybe 15 years ago. However, I never heard any major players use it after that.
exactly. that was the same for me, "what the heck is litespeed?!" was my reaction, then i noticed it's been there for a few years already.

and the fact that it's a drop-in replacement for apache config files is just mind-boggling. who in their sane mind would want to reproduce that complexity?

I have used the commercial version of Litespeed a few times, quite impressive, featureful and fast, but configuration and management was a PITA.
IIS dying and Nginx replacing it might be due to Microsoft encouraging the use of Nginx with .NET (the artist formerly known as .NET core) ASP servers.

.NET already has a server embedded in it (Kestrel) but Microsoft documentation points to Nginx as the solution once you've moved out of development and into the wild, when deploying on linux.

https://docs.microsoft.com/en-us/aspnet/core/host-and-deploy...

I'd also assume the heavy use of CloudFlare makes gathering statistics extremely difficult.

Cloudflare uses nginx with their own patches (including changing the server name) so nginx usage is > 50% (w3techs) or > 40% (Netcraft).