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Hi Dbadini - there are a number of potential causes so I'd start by using the reachability analyzer to ensure that you have the correct connectivity in place - https://docs.aws.amazon.com/vpc/latest/reachability/what-is-reachability-analyzer.html. I'd also continue to troubleshoot through VPN logs and using tools such as netstat, netcat, nmap or telnet to test connectivity to as RDP should only require port 3389. There are other connection options available if you'd prefer not to use RDP such as Systems Manager Session Manager https://docs.aws.amazon.com/systems-manager/latest/userguide/session-manager.html. Finally check that the windows server has the correct firewall settings enabled and that you've configured incoming connections correctly server side. Hope this helps :)
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