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Re:Windows app to get you Let's Encrypt SSL Certificate in l... by simonsarris on Friday April 15, 2016 @10:09AM (#11504384)
Seconding that tool, but be sure to read all of the relevant Wiki pages before you use it, and if your IIS is hosting multiple sites do not miss:

https://github.com/Lone-Coder/letsencrypt-win-simple/wiki/HT...

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