I'm trying to setup Let'sEncrypt-win-simple with SmarterMail 16. SmarterMail 16 is using IIS on a Windows Server 2012 R2 server.

 

So I run the letsencrypt program and it creates the .well-known/acme-challenge folder under the MRS folder like I would expect, and it drops the challenge file in it like it's supposed to. However, the LetsEncrypt server can't read the file.

 

So I start looking around and I find that every subfolder and file that I create inside the MRS folder for SmarterMail generates a prompts for a login and gives a 401 error if I try to access it via browser. And if I put in a valid Smartermail login when prompted, it accepts the credentials and gives a bad request error.

 

For the life of me, I have not been able to figure where SmarterMail is intercepting the site in IIS and using Smartermail to authenticate for the folder that Let'sEncrypt creates.  If I drop a test file in the ./interface/ folder, the file can be read just fine using the anonymous IIS access.

 

Anyone have any thoughts on where I'm not looking in the right place to make the letsencrypt challenge file accessible from the outside?

 

Thanks,

 

Eddie