Please fill out the fields below so we can help you better. Note: you must provide your domain name to get help. Domain names for issued certificates are all made public in Certificate Transparency logs (e.g. https://crt.sh/?q=example.com), so withholding your domain name here does not increase secrecy, but only makes it harder for us to provide help.
My domain is: remote.fitch.ca, smtp.fitch.ca, access.fitch.ca
I ran this command:
letsencrypt win-simple: manual cert, remote.fitch.ca
It produced this output:
The ACME server was probably unable to reach http://remote.fitch.ca/.well-known/acme-challenge/…
My web server is (include version): IIS 7.5
The operating system my web server runs on is (include version): Windows 2008 R2
My hosting provider, if applicable, is:
I can login to a root shell on my machine (yes or no, or I don’t know): Yes
I’m using a control panel to manage my site (no, or provide the name and version of the control panel): No
The version of my client is (e.g. output of
certbot --version or
certbot-auto --version if you’re using Certbot):
A note, this doesn’t work on multiple web servers. I’ve tested the challenge file, and it’s present and accessible both inside the network and from external (phone) devices. DNS resolution seems to be fine. I’ve renewed these domains regularly for several years and then all of a sudden multiple servers fail, though they serve up the files as required.