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I have a conundrum going on in my head for sometime now.

It involves IP addresses, VPN and VPS.

The scenario is this:

I have two Virtual Private Servers (VPS), let's call them VPS 1 and VPS X.

Now, let's say the following are the IP Addresses of each machines:

  • my Desktop's = 192.69.69.69
  • VPS 1's = 192.39.39.39
  • VPS X's = 192.75.75.75

(A) My first question is, if I use my desktop to remote desktop connect to VPS 1, what is the IP address that will show up in VPS 1's (access) log?

If my wild guess is correct, it's 192.69.69.69. But I still need confirmation that my answer is correct.

(B) Then after connecting to VPS1, I successfully set up a Virtual Private Network (VPN) inside VPS 1. I have no question about this. :)

(C) Second question, Using the VPN i just set up in VPS1, I used my desktop and connected to VPN X, what's the IP address that will show up in VPS X's (access) log?

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It depends on the configuration of the vpn, and Amazon.

1st Question:

yes, it should be

If not, Amazon is using some gateways/loadbalancer in front of VPS1. But I would think, that this is very unlikely.

2nd Question:

In a normal vpn gateway configuration it would be VPS 1's IP

If it is correctly configured VPS 1 can pass the IP of your computer to the Backend (VPS X). This isn't usually the case.

Again, if this is a special Amazon-related software it could be something else.

  • Thank you Ludwig, thank you for giving your answer. Assuming its not Amazon. another question please, is there a way that my original IP (192.69.69.69) will be traced that it logged in to VPS X? – Ben Daggers Dec 6 '16 at 16:09
  • @BenDaggers I updated my answer. It could be possible. Both VPS 1 and VPS X would need configurations for that. – Ludwig Behm Dec 6 '16 at 16:15

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