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Concerns over using remote desktop

I have someone in our office who wants to start using Remote Desktop while he is out of town on business.  I am the network admin but don't really know a lot about the secrity issues that could arise.  Given that he is the boss, I want to advise and do the right thing.  Is it a secure method to work away from the office?
4 Solutions
combine it with a VPN.. thats what every place i work with/setup uses.  I dont really know about the security implications about shooting a TS session clean across the net unencrypted, ive honestly never TS'ed anywhere unless it were over VPN.

Unless the NSA is after you, not many places are going to crack your VPN traffic.
Lee W, MVPTechnology and Business Process AdvisorCommented:
RDP protocol is encrypted.  Data won't be easily visible to others.  The problem I'd see is that to use Remote Desktops, you'd have to open a hole in the firewall (assuming you have one) so that he could connect directly to his PC.  You can mask this somewhat if you can tell your firewall to open, say port 4512 and forward it internally to 3389 (of course NAT will do this for you).

Ultimately, I agree with zerofield - if you can, setup a VPN and have the user come in that way.  The more layers of security, the more secure you are (of course, the more complicated you make things too, but that's another issue...)

Oh, and how's his password and your password requirements.  Complex or do you think he might be using "boss" as the password?
Ron MalmsteadInformation Services ManagerCommented:
It is fine...i use it all the time, and we have a very large user base....just don't create generic logons for multiple users with terminal services permissions enabled, or you could find yourself with a disgruntled employee who wants to sabatoge you.
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