VPN & Remote Desktop Issues

MikeTowers · Dec 5, 2012

Hi,

Work have just bought me a new Mac Air which I want to use to connect via VPN and remote desktop to my work machine. I'm a software developer so I'm techie but I'm new to Mac's so please bare with me.

Anyway, I've downloaded the Microsoft remote desktop client for Mac and installed it. I've setup the VPN connection and test it and it says it's connected. However, when I try connecting to my work machine using the remote destop client and the IP address it says it can't connect.

At this point I'm a little stumped as I've already said I'm new to Mac's so I'm not really sure where to start looking. One thing though, I have an IPad 2 which I've setup the VPN on and I'm using the Mocha remote desktop client app to connect to my work machine so I'm reasonably confident it's not the VPN that's causing the issue but something to do with the Microsoft remote desktop client.

Any help would be appreciated.

Thanks

Mike

GGJstudios · Dec 5, 2012

I use TeamViewer, which is free for personal use and works with Windows, Mac OS X, Linux, Ubuntu, iPhone, iPad, etc. It's very secure and quite simple to set up and use (no messing around with ports), which comes in handy if providing remote support to those who aren't very computer literate. You can talk them through the setup on their end and be connected to them in less than a minute. I prefer it over LogMeIn because it includes free file transfers between computers, a feature I use frequently.

MikeTowers · Dec 5, 2012

Hi,

Does TeamViewer need the remote machine to accept an invite like some of the apps I've looked at or is it a proper remote desktop client like the Microsoft client?

Mike

GGJstudios · Dec 5, 2012

MikeTowers said:
Hi,

Does TeamViewer need the remote machine to accept an invite like some of the apps I've looked at or is it a proper remote desktop client like the Microsoft client?

Mike

You can do it either way. You can require that the invite be accepted at the other end, or set it up with a predefined password and connect with no one at the other end. I've used it for years to support Windows and Mac users.

MikeTowers · Dec 5, 2012

And will TeamViewer work ok through our company vpn or is http based?

maflynn · Dec 5, 2012

MikeTowers said:
And will TeamViewer work ok through our company vpn or is http based?

Its http based and you'll need to install something on the other computer to work.

Unlike RDP which is built into windows other remote control apps need to install a small app to allow the communications.

I'd be careful of installing any product on your work computer or server as it might violate company guidelines.

As for your problems looks like the VPN may not be fully working. Can you access your company's intranet once you have the VPN up? I use VPN and can use RDP to access the servers to which I'm responsible.

robvas · Dec 5, 2012

I used CoRD, the Microsoft RDP program always seems to freeze up on me when connecting or disconnecting.

Anyway, I doubt the RDP program is the problem. Can you ping the computer you are trying to connect to from the Terminal?

I would guess you are either not 'Sending all traffic over VPN connection' (you can enable that in the Advanced settings of that particular connection.

MikeTowers · Dec 5, 2012

Installing third party software on my machine is not an issue. As a software developer we are allowed to set up our machine ourselves within reason. However, I would prefer to use a remote desktop client if possible. I've now found out how to ping things from a Mac so I'll give that a try when I get home and report back.

MikeTowers · Dec 7, 2012

Right, I've tried ping and traceroute while is says I'm connected to the vpn and it can't see my work computer. Interestingly I've just noticed that my IPad can't connect to my work computer if it's connected to the vpn via wifi but can on 3g. Strange this as my Windows 7 laptop has no issues what so ever. Will confirm later if I'm really logged into the vpn using teambuilder to connect to my work machine.

Panch0 · Dec 7, 2012

I have always found that when accessing my work resources remotely through VPN, it works best if I use the FQDN instead of just the machine name - machine.company.local vs. machine

You want to use the internal domain name, or the internal IP Address, not the external address. My company uses company.net to connect to the VPN, but when I connect RDP, it is company.local.

It depends on the VPN client you are using, but my experience has been that MAC VPN Clients don't deal with routing exactly the same way that windows clients do. if you just enter the machine name without an explicit domain, the RDP client is probably going to look on your local network and ignore the VPN tunnel.

Since your iPad works on 3G but not wireless, you may also have a router problem - check that IPSEC and or PPTP Pass-Through are enabled in the router set-up.

RandomKamikaze · Dec 7, 2012

Is your home network and work network using the same IP range and subnet?

What VPN Client is your Win 7 laptop using?

krravi · Dec 7, 2012

MikeTowers said:
Right, I've tried ping and traceroute while is says I'm connected to the vpn and it can't see my work computer. Interestingly I've just noticed that my IPad can't connect to my work computer if it's connected to the vpn via wifi but can on 3g. Strange this as my Windows 7 laptop has no issues what so ever. Will confirm later if I'm really logged into the vpn using teambuilder to connect to my work machine.

I connect to work using Mac's on my work VPN and have no issues reaching my desktop at work. Same with iPad as well.

I would say something is preventing DNS lookups once you are in the VPN. Is your office VPN security such that only office computers are allowed to connect? Or any computer can connect as long as you have the VPN software installed?

Oh and BTW Teamviewer is slow and not fit for development under remote. RDP rocks when it comes to speed.

We use cisco and so I didnt have to install anything on the mac for VPN. Used the built in VPN configuration in network to do that.

Note down your DNS address at work and see if you can ping that from your Mac. If so,then add that DNS server under your network preferences and see if that works.

maflynn · Dec 7, 2012

robvas said:
I used CoRD, the Microsoft RDP program always seems to freeze up on me when connecting or disconnecting.

I've used this as well and found it to be a great app. I use CoRD (and RDP) to connect my work's servers and found CoRD to be a better product on the Mac

JHUFrank · Dec 8, 2012

robvas said:
I used CoRD, the Microsoft RDP program always seems to freeze up on me when connecting or disconnecting.

Anyway, I doubt the RDP program is the problem. Can you ping the computer you are trying to connect to from the Terminal?

I would guess you are either not 'Sending all traffic over VPN connection' (you can enable that in the Advanced settings of that particular connection.

What he said. 99% of all VPN problems on an Apple in my organization that I deal with are this.

MikeTowers · Dec 10, 2012

An update, I can confirm that I can definitely connect to the VPN. Using my IPad with 3G and Team Viewer I connected to my work machine and from there onto the VPN box and could see that my Mac was connected to the VPN. However, I can't ping any of the machines on the work network either by machine name or IP. Further I still can't connect using RDP. I don't believe that this is an issue with my router as my Windows 7 laptop can connect happily using the same box.

Panch0 · Dec 10, 2012

Are you using the VPN client built into OS X, or a 3rd party client? In either case, there should be some manual configuration settings that you can enter for the connection. These can control the domains that the Mac will look for on the VPN. Usually this stuff gets set up during negotiation with the VPN server, but you may be able to tweak it.

I've been using Cisco AnyConnect for a few years now, so I don't remember the specifics of what settings were available.

You might also try nslookup, to see what DNS server the Mac is trying to find your VPN resources on - I would guess that it's the same one it is using for regular internet stuff. If the VPN is configured correctly, it should be looking for the internal DNS server on your work network.

maflynn · Dec 10, 2012

MikeTowers said:
An update, I can confirm that I can definitely connect to the VPN.

One thing I remembered when I connect to my work network via VPN and that's the fact I need to use a web browser and go to a website first. That is I hit msnbc.com while on VPN. Its odd I know but I cannot connect to any work resource without doing that first (even though I'm authenticated). It may be a long shot for you, but it can't hurt to try.

MikeTowers · Dec 10, 2012

maflynn said:
One thing I remembered when I connect to my work network via VPN and that's the fact I need to use a web browser and go to a website first. That is I hit msnbc.com while on VPN. Its odd I know but I cannot connect to any work resource without doing that first (even though I'm authenticated). It may be a long shot for you, but it can't hurt to try.

I know exactly what you mean my Window 7 box needs a ping to the IP of my work machine otherwise it takes 3 or 4 attempts before the RDP will connect.

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