Is there any information or tool that you encourage to use IIS / Windows to submit requests to Let’s Encrypt?
The client list has a number of options for Windows. ACMESharp and letsencrypt-win-simple have IIS support.
There’s no official recommendation or anything like that for a client that runs on Windows, so it’s up to you to decide which fits best.
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Thanks for the quick reply. I’ll checkout those options. It looks like Certify, ACMESharp, and letsencrypt-win-simple are somewhat active projects.
I think what you’re doing at Let’s Encrypt is important so thank you. 10-45% of websites (measurement methodology varies:
https://news.netcraft.com/archives/2016/12/21/december-2016-web-server-survey.html) so hopefully getting automated certificates will get much easier for IIS in the future.
So far I have not been able to get any of those to work on Windows/IIS systems. Sadly.
I have LetsEncrypt working on several Linux based servers.
The ultimate goal would be to have first-party support for ACME in all major server software, including IIS, so that TLS "just works". Caddy has shown how this can be done and hopefully other vendors will follow suit. I seem to recall that there's a feature request that can be voted on for this somewhere, but I can't seem to find the link right now.
If you'd like to share some of the details of the issue you're running into (preferably in a new thread 
), someone on the forum can probably point you in the right direction.
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one of the key challenges with windows is the use of PFX format and some other differences
powershell is certainly the way to go however writing reliable powershell modules can be tricky (secured windows environment etc).
Any of the modules written in Python or other programming languages will work on windows with a bit of tinkering.
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