How does a VPN work with something like Dropbox?

VPN
1

Hi everyone, I’m new to VPNs and had a question. If I’m using a VPN and also using a service like Dropbox, is my data (the files I work on that are stored within Dropbox) only going to Dropbox servers, or does it also go to the VPN servers? Is this where a VPN’s logging policy comes in?

Apologies if these are silly questions. I just want to make sure I understand how a VPN works with cloud storage and my files.

Thank you.

2

Think VPN as shipping service, instead delivering yourself, you take your data to VPN, and they do the rest of the trip. They can check your traffic if they want. Some data are only encrypted between you and the destination, like Dropdox, so even if VPN check your traffic they would not know content of your data to Dropbox. Since they are the one delivering your data, like shipping service, they will know it goes where and when, from where, how much data. etc.

3

The one legitimate concern about using a service like Dropbox and a VPN is that it can easily be used to de-anonymize you.

Dropbox has a minute by minute record of what IP you’re connected from. So if you’re connecting to a VPN for anonymity while running something like Dropbox on your system, you can be trivially de-anonymized (even if your VPN doesn’t keep logs).

4

While traffic does go through the VPN servers, it’s only a pipe, and isn’t stored there.

5

A shipping service is a good analogy, I’ll probably steal that in the future.

They can keep a record or who sent a package to where, if it was a big package or a small one, but they don’t know if the contents was heroin or skittles. Unlike a shipper, the contents of encrypted VPN are a lot harder to open than a cardboard box if the “shipper” decides to act maliciously.

6

Thanks for your answer!

7

Here comes why you should opt for a VPN with shared IPs. Sure, you connected to your dropbox through IP 387.977.222.234, but there were at least a thousand others so I doesn’t prove that I did that other thing.

8

Thank you for your answer.

9

How do we know if the messages are really encrypted when using VPN?

10

This guy already knows his legal defense :stuck_out_tongue:

11

Unless you’re using GRE for VPN (Which wouldn’t be a smart decision in this situation), VPN traffic is usually encrypted using TLS, unless you’re doing site-to-site VPN, which IPSec is usually the common one there. Unless you’re building a GRE tunnel yourself (which is more for firewall bypass anyway), TLS is used.

Also, use wireshark, it’ll show you the packets :grinning_face_with_big_eyes:.

12

There is always a chain of trust. Perhaps you could trust more the official OpenVPN application to connect to your VPN service of choice, rather than their proprietary client.

13

Best to not connect to anything that can be linked to you of course haha