The assumption is that the incoming traffic is blocked by On-Prem Windows firewall or Cisco ASA.
To troubleshoot it:
- I would not recommend to use ping to check the reachability.
- Make sure, that you have some service, which listens to the incoming requests on your On-Prem Windows Server. For example, IIS (port 80)
- Check if your On-Prem Windows firewall allows that inbound connection. If not, enable it.
- Check if your Cisco Firewall allows connections from Azure to your windows server.
- Check if your NSG, which is assigned you your Azure Server is not blocking your outbound connection (normally, it is allowed)
- Enable real-time monitoring on your On-Onprem Windows Server, Cisco ASA, and Azure Windows Server (NSG flow logs)
- On your Azure Windows Server run
telnet 10.5.11.50 <listening port>and check all your logs.
After that, if not fixed, you could check the next assumptions:
- misconfigured IPSEC tunnel