Cannot access my remote desktop outside of home network

VPN
1

I have an iMac that is dual booted to run Windows 10. When working remotely, I am always booted into Windows and that is what my query is in regards to. I use Microsoft Remote Desktop to access my iMac from my MacBook Air. I am able to access my iMac just fine when I am on my local network, but I cannot access it elsewhere.

I have a VPN set up on both my iMac and my MacBook. This seems to make no difference. My MacBook still will not connect to my iMac unless I am on my home network.

​

Edit: https://github.com/trailofbits/algo/blob/master/docs/deploy-from-ansible.md

I used this to create a cloud server through Digital Ocean. Then I configured Wireguard Tunnels on my desktop and laptop. According to whoer.net, both my desktop and laptop are showing as being connected to the Digital Ocean server I created. Yet, I still cannot use my remote desktop unless I am on my home WiFi. What is it that I am still missing? I’m not sure if I have my users configured correctly on the host machine where I set up Algo, but that was the one piece of the directions that seemed to be lacking so I was not sure exactly what to do there. I also am using an Xfinity hotspot for testing purposes as it is the only other means I have in my apartment for connecting to the internet outside of my own WiFi network. I’m not sure if Xfinity has any sort of security in place to prevent me from accessing my local server.

​

2nd edit: Actually, it appears my remote desktop will no longer connect on any WiFi. I’ve tried adding different IPv4 addresses as new PCs based on info returned to me through the Shell as well and none of them will connect nor will my original remote desktop which was working fine on my local network prior to my doing this. It only connects when Wireguard is deactivated on my desktop

2

Do not do that. If you have not already disable that. Do not do that. Ever.

3

Not sure why all the comments are being weird. I didn’t see the original post before the edit, but maybe it has something to do with that.

Anyways, from what I’m seeing, it sounds like your issue is that you’re connecting to a general, public VPN, and not your own “call home” VPN.

I would check and see if your router supports creating a VPN (which should be the type of VPN that you’re looking for). If it doesn’t, you may be able to flash your router firmware to DD-WRT, which would definitely allow you to do that. The type of VPN you’re currently using with Express VPN is useful for anonymous browsing / security and will likely have better performance than your own VPN that you would run off of your router. Express VPN is also useful if you want to access sites and services in another region than the one you’re currently in.

Hopefully that helps, but let me know if I can clarify anything.

4

I don’t think anyone here will want to help you do this. At least, I hope not.

5

Depends on how the VPN works. If it puts you in a separate subnet then you would need a static route on your router.

6

Install wireguard on a vps and connect both computers to it

7

Did you figure out the problem?

8

Could you explain what OP should not be doing in a little more detail?

opening RDP port to the open internet is probably not a good idea even though rdp has authentication. is that what your concern is?

9

Yeah I think the details in my post articulate that I know that already. Yes, I did close the port. I was just trying to see if it would work or not. This doesn’t really answer my question.

10

I opened a port and immediately closed it. I did so just to be thorough as I attempted to figure out why I could not connect off of my home network and I only included that in the post so it would be abundantly clear what I had and hadn’t tried. I know that doing so is risky and I had no intention of leaving it open, all of which I explained in the post, but everyone still jumped down my throat and my question wasn’t being answered as a result so I just removed that part of the post all together.

Thanks for this. I’m attempting to set up a VPN server now. I’ve never done anything like this before but I have a general idea of how to move forward so I’m just going to tinker for a bit and see where I end up.

11

Help me troubleshoot why I cannot connect to my remote desktop outside of my home network while connected to a VPN? I didn’t realize that was so controversial. Apologies.

12

Thank you. I appreciate at least one comment that gives me something additional to go on.

13

I *think* I did this but still the problem isn’t fully resolved. Check out my edit.

14

I’m getting there. Check out my edit and see if you have any thoughts

15

Ah yeah you’re going to need a VPN to your network, not to ExpressVPN’s servers

16

Hey, that’s the only way to learn. Now you know that it’s a security issue (even tho it sounds like you already did, but were accepting of the risk). And after tinkering, you’ll also know how to setup a VPN server. Networking shit is hard and confusing, and I think too many people forget that everyone has to start somewhere and that this community should be for helping teach others what you know.

17

My bad. I misunderstood. I thought you were exposing the RDP port to the internet (massive security hole).

In that case, you’ll need the vpn server to be on the same network as your pc. Also, you’ll need to make sure your vpn settings to allow access to network resources.

What router are you using?

18

Where is your VPN endpoint? On your router? Can you ping between the devices while on the VPN?

19

Thank you for this! I am now attempting to set up a VPN server using Algo and Digital Ocean. I’ve never done anything like this before so I think I might have to run it in Terminal a few times before it completes successfully, but hopefully I can figure it out.

20

Thank you! This is what I ended up doing: https://github.com/trailofbits/algo. Everything ran smoothly and my laptop is now connected to the server I created. I’m now just trying to get desktop connected to it as well.