Remote desktop from a Mac or iOS gives error 0x3000008

Question

I have a load balancer (HAProxy) in front of two Remote Desktop Gateways (2012R2). When connecting from a Mac or an iOS device I receive an error 0x3000008 on the client side and in the event logs on the gateway server I see:

The user "user@keyman .com", on client computer "X.X.X.X:36008", has initiated an outbound connection. This connection may not be authenticated yet.

I've disabled enforcebindings in the registry.

Works fine from a Windows client.

Answer 1

Hi,

Below post seems similar with your issue.
https://social.technet.microsoft.com/Forums/ie/en-US/c24a615a-a388-44d3-aa99-b940eedb12d8/rdp-on-androidios-issues-error-0x3000008-we-couldnt-connect-to-the-gateway-because-of-an-error?forum=winRDc

The answer mentioned "The problem comes from the fact that the RDP client (MAC, iOS, Android...etc) uses absolute URI in the SSL tunnel. WAP server supports only relative URI. Absolute URI support has been added to Azure AD Application Proxy recently. If it's possible it is recommended you should use Azure AD Application Proxy. The Product Group team has been informed about this and is working on finding a work-around. But at the moment we don't have plans on fixing the issue in WAP (2016)."

Have you tried to skip the HAProxy and directly connect to the RD Gateways ? Does the issue persist?

Thanks,

Eleven

If the Answer is helpful, please click "Accept Answer" and upvote it.