Upgrade from 4.1.6 on Server 2008SP1

We recently started receiving “Validation of the required challenges did not complete successfully”. Fetching http:\…Timeout during connect. I believe port 80 is already open.
We are still running ver. on a WIndows 2008 SP1 Server. Will we be able to do an in place upgrade to 5.5 as we fulfill the requirements of SP1 and .Net higher than 4.6.2? I can’t upgrade the server at the moment and would like to continue using the product.
Thank you

Hi, v4.1.6 should still work even though it’s not the currently supported version. Timeout during connect suggests that port 80 is indeed not open, or you care blocking IP addresses geographically or something else.

Feel free to email support at certifytheweb.com with more details, we’d need your domain and the log file for your managed certificate.

If you can run .net 4.6.2 you can likely run the latest version of the app OK (the OS isn’t supported because it’s no longer supported by Microsoft) but you should probably test on another test server first.