Certbot for Windows Timeout during connect

My domain is publicly reachable when I have my IIS site turned on so I don’t think this is a DNS issue (I’m not an expert, though). I shut down IIS and made sure nothing else was listening on port 80. But certbot gives me the timeout error everytime. I’m using an AWS EC2 Windows instance and just setup the domain using AWS Route 53.

My domain is:
njsld.org

I ran this command:
certbot certonly --standalone

It produced this output:
Saving debug log to C:\Certbot\log\letsencrypt.log
Plugins selected: Authenticator standalone, Installer None
Please enter in your domain name(s) (comma and/or space separated) (Enter ‘c’
to cancel): njsld.org
Obtaining a new certificate
Performing the following challenges:
http-01 challenge for njsld.org
Waiting for verification…
e[31mChallenge failed for domain njsld.orge[0m
http-01 challenge for njsld.org
Cleaning up challenges
e[31mSome challenges have failed.e[0m
e[1m
IMPORTANT NOTES:
e[0m - The following errors were reported by the server:

Domain: njsld.org
Type: connection
Detail: Fetching
http://njsld.org/.well-known/acme-challenge/Vr5kAnQ5tN4SuXe3aEzLj92uG1X0YUb3CXZplTLSkfU:
Timeout during connect (likely firewall problem)

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):
IIS 10.0

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

My hosting provider, if applicable, is:
AWS EC2

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):
certbot 1.7.0

1 Like

Hi,

I personally don’t think you need to shutdown your IIS instance when getting a certificate, which will be painful when renewing.
For your error message, do you have any firewall in place that only granted access to IIS webserver (not sure if that’s possible, i’m not familiar with IIS and Windows Server to be honest).

If you know your website’s full path (absolute path to your website root folder), you may be able to use --webroot to obtain a certificate without shutting down your webserver.
The full command would look like this: certbot certonly --webroot -w Your_Root_Path_in_quotes -d njsld.org Official Document

P.S. When you are obtaining a certificate for your root domain, it’s always better to include the www version in case a visitor added www in front when they type in your URL. If you want(and can) do this, please also resolve your www hostname to the same IP.

Thank you

1 Like

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