Try creating a test challenge file and see if it can be reached from the Internet. echo success > C:\inetpub\wwwroot\.well-known\acme-challenge\test-1234
Well the file is not found (404).
So the directory in use is not the one where you think it should be.
First, let's be sure the file was put there correctly:
[from a cmd prompt - please show] dir C:\inetpub\wwwroot\.well-known\acme-challenge\
Yes, both HTTP and HTTPS show the text file when it has the .txt extension.
IIS is not liking files without an extension.
You have to set a MIME TYPE for such files to "text/html"
Not sure right now where that is in Windows.
We can consult with the Google Gods for that - LOL
c:\inetpub\wwwroot>certbot certonly --webroot
Saving debug log to C:\Certbot\log\letsencrypt.log
Plugins selected: Authenticator webroot, Installer None
Please enter in your domain name(s) (comma and/or space separated) (Enter 'c'
to cancel): FileIT.org
Obtaining a new certificate
Performing the following challenges:
http-01 challenge for fileit.org
Input the webroot for fileit.org: (Enter 'c' to cancel): C:\inetpub\wwwroot
Waiting for verification...
β[31mChallenge failed for domain fileit.orgβ[0m
http-01 challenge for fileit.org
Cleaning up challenges
β[31mSome challenges have failed.β[0m
β[1m
IMPORTANT NOTES:
β[0m - The following errors were reported by the server:
If not, open cmd prompt as admin, then try it again.
If so, then maybe the folder permissions are blocking certbot from putting the file there and we may need to run it with more verbosity -vvv to see why this fails [and add --dry-run so you don't start hitting limits].