Can't RDP from Mac to Windows Jump Server

arvindrajendran — Sat, 02 Mar 2024 19:05:22 GMT

Dear Community Members,

I'm facing a strange issue. I use 2 machines related to my work. One is a Windows Laptop and another one is a Macbook.

We have a server, which acts as a Jump Box. We use Global Protect VPN for connecting to that JumpServer.

Now the issues is that, i can access this server after connecting to GP from my Windows Laptop. But from my Macbook, i cannot RDP to this server after connecting to GP.

I did some tracing using Wireshark and one strange thing i noticed is that from my Macbook, the RDP negotiate request is not reaching the Jump Server whereas i could see negotiate request and also the response being sent for my Windows laptop in the Jump Server.

Below is a description of the Wireshark Logs:

On MAC:

MAC > Server | TCP [SYN]

Server > MAC | TCP [SYN,ACK]

MAC > Server | TCP [ACK]

MAC > Server | RDP Negotiate Request

Server > MAC | TCP [RST,ACK]

On Server:

MAC > Server | TCP [SYN]

Server > MAC | TCP [SYN,ACK]

MAC > Server | TCP [ACK]

Server > MAC | TCP [RST,ACK]

Can any of you advise what needs to be checked so that i can get the RDP to working from my Macbook.

Re: Can't RDP from Mac to Windows Jump Server

reaper — Tue, 05 Mar 2024 11:36:21 GMT

Did you check your threat log in case your RDP request is somehow matching a vulnerability?

Re: Can't RDP from Mac to Windows Jump Server

arvindrajendran — Sun, 10 Mar 2024 07:06:51 GMT

We have a separate firewall team and i was checking with them regarding the same. They are also not able to identify why the request is being dropped. Probably in the next two days i will get to know something as they arranged a TAC call. I'll share the findings here.

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Can't RDP from Mac to Windows Jump Server

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Re: Can't RDP from Mac to Windows Jump Server