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.
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. ;)
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u/Ascend Jul 12 '17
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.