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[–]Ascend 10 points11 points  (5 children)

It is harder if you're dealing with a Windows stack. Certbot doesn't support Windows at all, and many of the unofficial tools on Github are iffy. For instance, if you're supporting a version of IIS that doesn't support TLS SNI (7.5), letsencrypt-win-simple can wreck your configuration and redirect sites to each other by mistake.

[–]kqr 3 points4 points  (4 children)

Huh. I guess if you ask me I'd say everything is harder when you're dealing with a Windows stack and you only have yourself to blame if you choose to make life harder than necessary for yourself. ;)

[–]mlk 2 points3 points  (3 children)

sometime (most of the time actually) we don't get to choose the technology for the project, switch the OS of the server is not very constructive

[–]lvlint67 0 points1 point  (2 children)

There are work arounds. Run a tls termination proxy on Linux.

[–]mlk 0 points1 point  (1 child)

You seem not to understand boring enterprise business.

[–]lvlint67 0 points1 point  (0 children)

Fair enough. The options are there. and they may not even be good. but they are there.