To fix these errors, please make sure that your domain name was
entered correctly and the DNS A/AAAA record(s) for that domain
contain(s) the right IP address. Additionally, please check that
your computer has a publicly routable IP address and that no
firewalls are preventing the server from communicating with the
client. If you’re using the webroot plugin, you should also verify
that you are serving files from the webroot path you provided.
My web server is (include version): Not sure, but website is hosted by SmarterAsp.Net
The operating system my web server runs on is (include version): See above
I don’t see a timeout issue here, since the webserver at least answers the request. What I find surprising: you use certbot, but the webserver behind the domain name identifies itself as Microsoft IIS.
I haven’t tried to be fair, but I don’t think Certbot plays well on Windows, generally. Usually people use one of the Windows clients in tandem with IIS.
I’m running CertBot via Terminal on my Mac, does this impact things? I seem to be going in circles on this as I can’t see anything wrong with what I’m doing yet I’m having no luck getting past the stage above.
If you insist to continue on your path (I would), ensure that the Internet can properly reach files located in the acme-challenge folder.
To that end, please place a brief test.txt file at: http://nortiman.com/.well-known/acme-challenge/test.txt
This won't work here out of the box. The op uses certbot on an unrelated system, so he has to copy the acme-challenge to the right path on the iis webserver.
@fentimanj: certbot is primarily meant to be used on the server which hosts the domain(s) and does not support windows systems. If you want to issue certificates on your windows server, you should use another client.