Could not issue an SSL/TLS certificate - PLESK Windows

[sakag]

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. crt.sh | 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:carle.co.in

I ran this command: generation from plesk windows

It produced this output:
Could not issue an SSL/TLS certificate for carle.co.in
Details

Could not issue a Let's Encrypt SSL/TLS certificate for carle.co.in .

Failed to connect to the Let's Encrypt server https://acme-v02.api.letsencrypt.org .

Please try again later or report the issue to support.

Details

Could not obtain directory: cURL error 28: Failed to connect to acme-v02.api.letsencrypt.org port 443: Timed out (see libcurl - Error Codes)

My web server is (include version): iis

The operating system my web server runs on is (include version): windows server 2012

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): Plesk Obsidian

The version of my client is (e.g. output of certbot --version or certbot-auto --version if you're using Certbot):

[MikeMcQ]

It looks like your server is not able to connect to the Let's Encrypt server. What happens when you do this from a command prompt:

curl -I https://acme-v02.api.letsencrypt.org/directory

[sakag]

its not opening from curl -I https://acme-v02.api.letsencrypt.org/directory
but from start https://acme-v02.api.letsencrypt.org/directory

[MikeMcQ]

I don't know why Plesk would issue the error you reported:

@sakag

Could not obtain directory: cURL error 28: Failed to connect to acme-v02.api.letsencrypt.org port 443: Timed out (see libcurl - Error Codes)

It looks like you can reach the LE server (with start anyway) and I can reach your server just fine. Maybe ask about this on a Plesk Forum. They even have one for older versions:

Plesk Forum

[rg305]

Is there any curl there anywhere?
dir c:\curl.* /s

[sakag]

ok
i will discuss on plesk forum

[sakag]

No
there is no curl anywhere

[9peppe]

that's strange. I have curl.exe on windows 11.

[petercooperjr]

There was also this announcement that Let's Encrypt is blocking Plesk as an emergency measure; I haven't seen any followup saying that they re-enabled it but I may have just missed it.

API traffic from Plesk is blocked

W…

Might not be related to your issue, though.

[JamesLE]

@petercooperjr

There was also this announcement that Let's Encrypt is blocking Plesk as an emergency measure; I haven't seen any followup saying that they re-enabled it but I may have just missed it.

Thanks for the reminder! It's been unblocked since about a day after that announcement.

[webprofusion]

@9peppe

that's strange. I have curl.exe on windows 11.

Recent versions of Windows ship with curl, old ones didn't. Incidentally Server 2012 only has about 1 year left before it doesn't get updates anymore, so anyone using it should migrate to newer versions as soon as practical.