Cannot connect to windows 10 laptop through Cisco VPN?

We are facing an odd issue that can’t resolve, and more pain for me that, my Google searches are failing me… so I’m reaching out. Here are some Similarities :

  • Cisco ASA Firewall configured for VPN using Cisco AnyConnect Client
  • Meraki MX content firewall running Advanced Security behind the ASA.
  • C-level, who’s used VPN for several years… so knows the ropes regarding connection.
  • we can recreate his issue using our laptop and desktops remotely.
  • Internally, have a new Windows 10 laptop, configured for Remote Desktop, using any RDS client.
  • we can ping the new laptop, using the IP address… and the FQDN from inside the network
  • we can also ping the new laptop, using the IP address… and the FQDN from outside (via VPN).
  • We can connect/RDS to the new laptop, using the FQDN from inside the network.
  • We can NOT connect/RDS to the new laptop, using the IP or FQDN from outside (via VPN)
  • Error received on the above, tells me the laptop is either not configured, or not on the network.
  • We can connect to any other server or workstation on the network that I’ve tried via VPN.
  • we have disabled the firewall on the laptop, no change.
  • we have disabled the antivirus (Webroot) on the laptop, no change.
  • The profile makes no difference in the above, the results are the same.

We have managed a lot of struggles. but this time it’s out of mind

Thus anyone… there who can solve this issue easily.

Great cheers.