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I'm not sure I necessarily understand your argument, so my apologies if I'm off here. In scenario 1, you do not gate access via VPN. Things are accessible via

I'm not sure I necessarily understand your argument, so my apologies if I'm off here. In scenario 1, you do not gate access via VPN. Things are accessible via the public internet. In scenario 2, you do gate access via VPN. Things are not accessible via the public internet. Someone compromises the VPN. They now have as much access as if there was no VPN and things were accessible to the public internet. In scenario 2, you are more secure than in scenario 1 until the VPN is compromised. You are then just as secure as you were in scenario 1. If you are not restricting access to a VPN in the first place, how would compromising a theoretical VPN result in greater access?

magicalhippo 6y ago
In the setups I've seen, once you've connected through VPN you're essentially on the LAN. If you compromise the SSH server, then you're also essentially on the LAN. Yes with the VPN you still have to compromise the server running the SSH service if that's the machine you want access to, but inside the LAN you now have a much greater attack surface. Of course if the setup is VPN -> firewall -> SSH to make sure only the SSH is exposed through VPN, then I agree you'd be more secure with VPN+SSH.
- cthalupa 6y ago
  But without the VPN, you're already the equivalent of on the LAN because all of these services are exposed to the public internet. In the discussion we're having, we're going from a setup where there is no equivalent to a private network because everything is public, to having a private network that only allows you access to the things that were previously public.
  - magicalhippo 6y ago
    No because I have a firewall in front of the SSH, as mentioned. I would assume a firewall is in front of the VPN as well of course. So either only SSH is exposed to the public, or only VPN is exposed. Without an additional firewall after the VPN, how is my LAN more protected with the VPN vs SSH?
    - cthalupa 6y ago
      Your goal is to protect SSH, not the VPN network. The VPN network is just a tool for protecting SSH. With your configuration, all that needs to exist is an SSH 0 day to gain access to the server. With a VPN, they need that AND a 0 day for the VPN software to gain access to the server. You can have a more complex setup with a VPN, but that isn't the discussion here - the discussion is securing SSH. If you want to provide VPN access to an array of other services, or as access to a corporate LAN or similar, then that's another conversation that has to involve the specifics of those services and that configuration. It's not what is being recommended here.
      - magicalhippo 6y ago
        Fair enough, guess I was restricting my view to my bubble. For a single server sure defense in depth should work, assuming you're not running the VPN on the same box.

magicalhippo 6y ago

In the setups I've seen, once you've connected through VPN you're essentially on the LAN. If you compromise the SSH server, then you're also essentially on the LAN. Yes with the VPN you still have to compromise the server running the SSH service if that's the machine you want access to, but inside the LAN you now have a much greater attack surface. Of course if the setup is VPN -> firewall -> SSH to make sure only the SSH is exposed through VPN, then I agree you'd be more secure with VPN+SSH.

cthalupa 6y ago
But without the VPN, you're already the equivalent of on the LAN because all of these services are exposed to the public internet. In the discussion we're having, we're going from a setup where there is no equivalent to a private network because everything is public, to having a private network that only allows you access to the things that were previously public.
- magicalhippo 6y ago
  No because I have a firewall in front of the SSH, as mentioned. I would assume a firewall is in front of the VPN as well of course. So either only SSH is exposed to the public, or only VPN is exposed. Without an additional firewall after the VPN, how is my LAN more protected with the VPN vs SSH?
  - cthalupa 6y ago
    Your goal is to protect SSH, not the VPN network. The VPN network is just a tool for protecting SSH. With your configuration, all that needs to exist is an SSH 0 day to gain access to the server. With a VPN, they need that AND a 0 day for the VPN software to gain access to the server. You can have a more complex setup with a VPN, but that isn't the discussion here - the discussion is securing SSH. If you want to provide VPN access to an array of other services, or as access to a corporate LAN or similar, then that's another conversation that has to involve the specifics of those services and that configuration. It's not what is being recommended here.
    - magicalhippo 6y ago
      Fair enough, guess I was restricting my view to my bubble. For a single server sure defense in depth should work, assuming you're not running the VPN on the same box.