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I am curious how safe I am if I use telnet through a VPN-tunnel to my webhotel? I thought that the information was encrypted between my computer to the vpn-providers default-gateway. But when it leaves the gateway on its way (through internet) to my webhotel its no longer encrypted? This is just a guess - Am I completely wrong? I sent this question to my vpn-provider in Sweden (dold.se) and got the answer (without tecnical explanation) - YOU ARE COMPELTELY SAFE USING OUR SERVICE

Would be glad if someone could explain how it really works in this case. I am just curious and normally use an SSH-klient (putty) to connect

cincerely

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So you pretty much answered the question, telnet is protected as long as it is in the VPN however there are a couple of thing you must realize.

  1. VPN does not protect against software running your computer, that is, if you have a piece of malware it may packet sniff your telnet session and get the password on your local computer before it goes into the VPN.
  2. Where ever the VPN ends you are going clear text, this may not be an issue if the VPN terminates into a known secure network however, how many of those are there out there?
  3. As I am sure you already know, if at all possible just use SSH, even across a VPN if the information is important.

Whether you are safe is a tough one, in general the only time I ever use telnet is for temporary access to set up SSH, I would suggest everyone do the same.

As a general rule, I do not trust anything I do not manage or control, even then it is dependent on where the devices are placed. I am not sure what a web hotel is or how you are using it but it sounds like it is out of your control so take appropriate precautions.

  • If I was running on the computer at either end I could help myself to ssh sessions thank you very much. – Joshua Sep 9 '15 at 15:32
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A VPN is like an armoured pipe: it protects the data as it transits between its two endpoints. However, it does nothing beyond these endpoint.

As I understand your question, you have a "VPN provider" that allows you to set up a VPN between your own machine, and some server on the VPN side. Your traffic between your machine and the VPN server will be protected against eavesdropping and alterations -- but only for that portion of the path. Once the data has reached the VPN server, it no longer benefits from the VPN. In particular, if you use plain telnet, then your precious data will travel unprotected between the VPN server and your "webhotel" (whatever you mean by that term).

While most low-scale, amateurish eavesdropping occurs near the end-users (WiFi is a boon for wannabe spies), this does not mean that other network parts are inherently safe.

Therefore, don't use telnet. If you want to do a safe telnet, you must use a VPN that goes from your home machine to the ultimate destination server (the webhotel).

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Generally speaking you should use SSH in preference to Telnet in all circumstances, if security is a priority.

Perhaps you're connecting to a legacy piece of equipment that does not support SSH however...

As I understand it, your scenario is that your VPN client is on your laptop, and that client is communicating with a VPN gateway provided by a provider. On the back-end, the provider handles forwarding the traffic that exits from the gateway to your company's network.

Assuming that the VPN is correctly set up, it should provide you with confidentiality and integrity and replay protection for that portion of the communication. You are correct that once the traffic exits the VPN, all bets are off. The statement that you are "completely safe" might indicate that they are continuing to encrypt the traffic in some way. On the other hand, it provides you with no real information about what security measures they are or are not taking...

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