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Re:HTTPS Deployment Growing by Leaps and Bounds by cm2187 on Friday December 23, 2016 @03:04PM (#13246915)
Let's encrypt takes care of most of the maintenance.

What would be great is for Microsoft to integrate let's encrypt into IIS. If someone feel like voting for that:

https://windowsserver.uservoice.com/forums/310252-iis-and-we...

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