Cannot renew certificate

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1

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My domain is:www.eiasm.org

I ran this command:wacs.exe --verbose

It produced this output:
[VERB] Constructing ACME protocol client...
[VERB] Getting service directory...
[DBUG] [HTTP] Send GET to https://acme-v02.api.letsencrypt.org/directory
[DBUG] [HTTP] Send GET to https://acme-v02.api.letsencrypt.org/
[EROR] (WinHttpException): Error 12175 calling WINHTTP_CALLBACK_STATUS_REQUEST_
ERROR, 'A security error occurred'.
[DBUG] Exception details: WinHttpException {NativeErrorCode=12175, ErrorCode=-2
147012721, TargetSite=Void Throw(), Message="Error 12175 calling WINHTTP_CALLBAC
K_STATUS_REQUEST_ERROR, 'A security error occurred'.", Data=, InnerException=n
ull, HelpLink=null, Source="System.Private.CoreLib", HResult=-2147012721, StackT
race=" at System.Threading.Tasks.RendezvousAwaitable`1.GetResult()\r\n at Sy
stem.Net.Http.WinHttpHandler.StartRequestAsync(WinHttpRequestState state)"}
[EROR] Wrapped in HttpRequestException: An error occurred while sending the req
uest.
[VERB] Exiting with status code -1

My web server is (include version):
IIS 7.5
The operating system my web server runs on is (include version):
Windows Server 2008 R2

My hosting provider, if applicable, is:
n/a

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):
[INFO] A simple Windows ACMEv2 client (WACS)
[INFO] Software version 2.2.9.1701 (release, pluggable, standalone, 64-bit)

I have been renewing my certificate for several years now with no problem. But now, I get the I/O error shown above. This looks to be some kind of TLS handshake problem but I'm not sure. Has anything happened recently with the requirements for compatibility. (e.g. I do not have, and cannot install TLS 1.3)

2

Welcome @pmouland

Yes, there has been a recent change which affects older Windows installs.

For a good explanation and how to fix please see: Renewal Error as "Initial Connection Failed" - #2 by webprofusion

4 Likes
3

In addition to what @MikeMcQ says I'd also obviously advise that you move your application workload to a newer version of Windows as a matter of urgency. I know it doesn't seem like 2008 was 17 yrs ago, but time flies and unfortunately security updates are no longer available for that OS, making it a significant risk if connected to the internet.

5 Likes
4

Problem solved. Thanks Mike for your prompt and correct response.

2 Likes
5

Noted. Thanks for the good advice.

3 Likes