Trouble With SonicWall Mobile Connect And Microsoft Remote Desktop On New MacBook Pro

Question

So I have been trying to get this sorted for the past three days and nothing I seem to do makes any difference. Hopefully someone here can help me out.

My workplace uses SonicWall to allow for remote log in to our machines there. For the past year or so, I have been using NetExtender on Windows 10 with my desktop at home and it paired with Microsofts Remote Desktop very well. Rarely had any issues of connectivity.

I recently bought the new MacBook Pro 16" (never used MacOS so I am still new to all this) but I wanted to set up the ability to get into my machine at work. So I followed the same settings I used with my Windows desktop and tried to connect. However, after I got through SonicWall, I would get a 0x240 error on the MRD application. Fiddled around with the settings but nothing really worked.

In doing the troubleshooting, I thought maybe it was my router that was blocking something? I don't know. But I set up my iPhones hotspot, connected my MacBook to that iPhone and tried to log in. To my surprise, everything worked as it did if I was on my Windows Desktop. SonicWall connected and then MRD booted up to my machine at work.

So I assumed it was something with my wifi connection and swapped out the router. After everything was setup with a new different router, I tried to connect again and I ended up with the same error at MRD that I did with the first router.

Additionally, when I take the MacBook to work and connect to their wifi, I can remote into my machine via MRD without connecting via SonicWall (as I am already on works network probably).

Does anyone have any inkling as to what I am doing that would cause this?

Answer 1

Turns out it was the subnet mask being the same as the remote server I was connecting to that was causing this issue.

So I changed the subnet mask in the network settings on my Mac with a manual input and then I tried to reconnect everything and it worked.

Any reason as to why this happened? Would love to understand what is going on. I am assuming Microsoft Remote Desktop was like, wait there are two machines that have the same DNS settings, I can't connect to this second one since I am already connected to this first one...?

Or am I just fundamentally misunderstanding how any of this works?