I too have experienced this (or a similar) issue, but with SAN type of certificates. Given a SAN certificate with the following hostnames (in this order): *.domain1.com *.domain2.com And an certificate monitor setup for foo.domain2.com - I indeed see the number of days until expiry, but a result that says something like "certificate cannot be verified". If I change the monitor to check for something like foo.domain1.com (the first domain on the cert) - everything goes green and works as expected. I'm guessing that it only works properly when verifying the first hostname on the certificate or something? For reference, I'm running on Windows 2008R2 (with the latest version of the Pulseway agent). Hope this helps -- let me know if I can provide any further details!