Could not issue an SSL/TLS certificate - PLESK Windows

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My domain

I ran this command: generation from plesk windows

It produced this output:
Could not issue an SSL/TLS certificate for

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

Failed to connect to the Let's Encrypt server .

Please try again later or report the issue to support.


Could not obtain directory: cURL error 28: Failed to connect to 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):

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

its not opening from curl -I
but from start

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

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:

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

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i will discuss on plesk forum


there is no curl anywhere

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

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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.

Might not be related to your issue, though.


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


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.


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