Also if I access a Proxy Server via Port 3128 to connect to my Azure Blob from my CloudBerry drive server do I also need port 443 opened from my CloudBerry Drive Server to the Proxy server as well.?
Drive has not officially been tested on Windows Server 2019, but we have no reported issues in the system from customers using it on that platform. If you want to use it and you run into issues you can let us know, and if you purchase and the issue cannot be resolved on that platform, the team would be more than happy to issue a refund.
I'll get back to you on your other question when I hear from support.