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I have to go out of town and stay in a hotel. During these days I will also have to work on some websites code and VMs that call external APIs.

Not being a system administrator nor a security specialist, my concerns are about someone sniffing the wireless traffic of my hotel room.

My question is: Does turning on a VPN protect all traffic that comes out from one PC or do I have to apply some specific configuration? Would even the Filezilla and VirtualBox traffic be encrypted?

I know few about this, but from what I know, my notebook will connect throught a secure tunnel, and once the request arrive at the other end of the VPN tunnel then there will be the open sea, and this is ok for me.

It would be just like connecting from home, using an ftp connection at home is not secure, but I'm confident that no one is sniffing me at home.

I would like to know that the connection from the hotel room to the other VPN endpoint is encrypted even for ftp and VMs. Beyond this I think that it would be the same as from my home, so using ftp and http will let someone else read the sent data.

I want to be sure that what I do in the room is not in plain text at least until the request reaches the VPN endpoint.

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If your VPN is configured properly all traffic is included. But, proper configuration is not guaranteed and in fact many VPN are not properly configured by default or cannot be configured properly at all. Typical problems are that they fail to support IPv6 or that the DNS lookup is still done through the local resolver and not through the VPN.

There are sites like dnsleaktest.com and ipv6leak.com which help you to determine if one of these typical problems affect you. It would be best to check this not only from the main system but from the virtual machines too to be sure.

The most secure way would be of course to use dedicated VPN hardware. In this case all traffic is going through this hardware and as long you don't have any additional network access (like WiFi in parallel to VPN) you can be more sure that there is no leak compared to a software only solution.

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  • It might be worth mentioning that there are now different types of "VPNs", some designed to only route certain traffic. So, "system level" VPNs will route all traffic from the system. Things like "browser-level" VPNs are more limited in scope.
    – schroeder ♦
    Jul 18 at 8:55
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I just would like to know that the connection from the hotel room to the other VPN endpoint is encrypted even for ftp and VMs. Beyond this I think that it would be the same as from my home, so using ftp and http will let someone else to read sent data.

I just wonna be sure that what I do in the room is not in plain text at least until the request reaches the VPN endpoint.

If your VPN is correctly configured (with encryption), all traffic from the device where the VPN is installed to the VPN endpoint will be encrypted, even the traffic from your Virtual Machine.

If you want you can check yourself when the VPN is up by using Wireshark to check if the traffic is encrypted.

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