Hi LetsEncrypt community,
I am using letsencrypt-win-simple 1.9 current version as of december 20th 2016.
I am using IIS 7.5.7600
I am running Windows Server 2008 R2 sp1
Issue :
Submitting answer
Refreshing authorization
Authorization Result: invalid
The ACME server was probably unable to reach http://s1.dev.nem.ru.is/.well-known/acme-challenge/b9fp7hX_f0lwW4PxTh9kQyNM
WS6zZEery0xeJUYp7y0
Check in a browser to see if the answer file is being served correctly.
This could be caused by IIS not being setup to handle extensionless static
files. Here’s how to fix that:
- In IIS manager goto Site/Server->Handler Mappings->View Ordered List
 - Move the StaticFile mapping above the ExtensionlessUrlHandler mappings.
(like this http://i.stack.imgur.com/nkvrL.png) - If you need to make changes to your web.config file, update the one
at C:\Program Files\LetsEncrypt\web_config.xml 
I have looked into several solutions to resolve this problem here is what I know so far:
- StaticFile has been moved up in priority
 - I have added mime types (thou I shouldn’t need it as web_config.xml file should cover it)
 - I can reach the machine from outside, I do get a text string.
 - I have changed the web_config.xml file for MVC and core settings
 
I am kind of running out of ideas, trying to figure out why I am not getting this to work. Do you guys have any idea for a step forward ?
 that I had been on a virtual private network connection to the network of that machine, there is no wonder that poor acme couldn’t connect.