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Windows 10 Working, OS X 10.12 Not

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Our company is switching to smart card authentication for RDP. I've successfully configured RDM on Windows 10 to connect to two separate RDP gateways: one requiring smart cards and one using telephone callbacks.

We're primarily looking at RDM for our Mac users, since Microsoft Remote Desktop on the Mac doesn't support smart cards. I've tried the same configurations that worked on Windows without success. I'm getting the error Failed to Connect to Host (131084). I've tried with and without Activate NLA selected.

Attached is a debug log. Are there any suggestions for tracking down the Protocol Security Negotiation Failure error? Should we be looking at the server settings or something that could be configured on the client?

Versions:
Windows Remote Desktop Manager Free 2.7.1.0
Mac Remote Desktop Manager Free 3.6.1.0

a2nessus1-log.txt
Clock3 yrs

Hi Donald,

Unfortunately, smart card authentication on a gateway is not supported.
The smart card authentication is only supported on the remote host.

Best regards,

Benoît Sansregret

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Clock3 yrs

RDM Smart Card Authentication on a gateway is working on Windows for us. Is there something different with the Mac OS version?

Clock3 yrs

Yes, the Windows version is using a component made by Microsoft to show the Embedded RDP Sessions.
Every other supported platform is using the FreeRDP component. Unfortunately, the smart card authentication for the Gateway server is not supported and I know it's not on their To-do list.

Sorry for the inconvenience

Benoît Sansregret

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Clock3 yrs

Thank you for the definitive answer.

Clock3 yrs