Some challenges have failed error

Help
1

My domain is: albertatriathlon.com

I ran this command: certbot certonly --webroot

It produced this output:
Saving debug log to C:\Certbot\log\letsencrypt.log
Please enter the domain name(s) you would like on your certificate (comma and/or
space separated) (Enter 'c' to cancel): albertatriathlon.com
Requesting a certificate for albertatriathlon.com
Input the webroot for albertatriathlon.com: (Enter 'c' to cancel): \web2020\c$

Certbot failed to authenticate some domains (authenticator: webroot). The Certificate Authority reported these problems:
Domain: albertatriathlon.com
Type: connection
Detail: 209.89.8.16: Fetching http://albertatriathlon.com/.well-known/acme-challenge/J8Qtje8ScGCBoHgX-h4wEy3XLtH1Gy_p7sZ1Nrs0xEE: Timeout during connect (likely firewall problem)

Hint: The Certificate Authority failed to download the temporary challenge files created by Certbot. Ensure that the listed domains serve their content from the provided --webroot-path/-w and that files created there can be downloaded from the internet.

Some challenges have failed.
Ask for help or search for solutions at https://community.letsencrypt.org. See the logfile C:\Certbot\log\letsencrypt.log or re-run Certbot with -v for more details.

C:\Users\Administrator>

My web server is (include version): IIS 7.0

The operating system my web server runs on is (include version): Windows Server 2019

My hosting provider, if applicable, is: IIS

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):1.24.0

2

Looking at your certificate history it looks like this is the first time you are trying with Certbot. The EFF stopped supporting Windows with Certbot over a year ago. You should not use it for new setups.

For IIS, Certify the Web is an excellent alternative. It is the first alternative mentioned in the EFF announcement: https://certifytheweb.com/
Certbot Discontinuing Windows Beta Support in 2024

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3

Yes, for IIS, you want to use some other client, probably Certify the Web (if you're a GUI fan), simple-acme (if you're a command line fan), or Posh-Acme (if you're a Powershell fan), though there are other choices too.

As for the problem you're getting, it looks like your site is not responding on port 80:

Make sure that your http site is working first, and then you should be able to get a certificate for https.

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