Knowledge Base

On Plesk for Windows server, Let’s Encrypt SSL certificate can not be issued for all domains with error 404: The filename, directory name, or volume label syntax is incorrect

Symptoms

On a Plesk for Windows server, issuing Let's Encrypt certificate on all domains in Plesk fails:

Error: Error: Could not issue a Let's Encrypt SSL/TLS certificate for example.com.
The authorization token is not available at http://example.com/.well-known/acme-challenge/.
To resolve the issue, make it is possible to download the token file via the above URL.
See the related Knowledge Base article for details.
Additional error details:
Invalid response from https://acme-v01.api.letsencrypt.org/acme/authz/_oRgI1kwh53Fr07VRtI-55Zj7NqY75KI5e41PCsQqow.
Details:
Type: urn:acme:error:unauthorized
Status: 403
Detail: Invalid response from http://example.com/.well-known/acme-challenge/uxIoK_7-BjsuBu362yQ_QD5ovykddVeyKEgfEAre9P8: "
HTTP Error 404.0 - Not Found
The resource you are looking for has been removed, had its name changed, or is temporarily unavailable
Accessing the authorization token on the URL from the error http://example.com/.well-known/acme-challenge/uxIoK_7-BjsuBu362yQ_QD5ovykddVeyKEgfEAre9P8 in a browser fails with the error 404.4.

Cause

The IIS module ApplicationRequestRouting is not enabled/installed or corrupted at Internet Information Services (IIS) Manager > server_hostname > Modules.

The following output is provided when accessing the link from the error message with enabled Failed Request Tracing:

ModuleName IIS Web Core
Notification MAP_REQUEST_HANDLER
HttpStatus 404
HttpReason Not Found
HttpSubStatus 4
ErrorCode The filename, directory name, or volume label syntax is incorrect.