I’m running a server on my LAN. It’s setup as a Webserver that’s only listening to local connections and a WireGuard VPN server. When I’m not at home, I establish a connection to the vpn.

The webserver is using http only. I’ve set up an nftables rule that masquerades requests from my vpn ip to my webserver in order to access those pages.

WireGuard is left with default settings, so it just establishes a connection between server and client.

Since I’m entering sensitive information on these websites, I’m wondering if the connection is encrypted through the vpn tunnel or if https is necessary to be on the safe side.

My LAN is trustworthy. VPN server and webserver are running on the same machine.

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    You are not serving local HTTP over VPN, according to the details you provide. Can you clarify this point? – schroeder Jul 19 '19 at 10:25
  • Can you explain "I do not route all traffic through that VPN, only DNS requests." – schroeder Jul 19 '19 at 11:43
  • I'm beginning to think that the answer is: it depends on how you set it up. All we are doing is asking for details on how you set it up. Please provide the full details. – schroeder Jul 19 '19 at 11:45
  • Again, this line "The vpn is not set to route all traffic through the tunnel." is the crucial one that you need to explain. What is sent through the tunnel? – schroeder Jul 19 '19 at 13:14

You question isn't very clear. You wrote:

I'm connecting to that server via VPN (wireguard).

And after:

I do not route all traffic through that VPN, only DNS requests.

So, if the HTTP stream between your client and your server isn't routed throught VPN, then the connection isn't encrypted.

At contrary, if you route the traffic to your HTTP server throught the VPN, then it's encrypted.

Nevertheless, keep in mind that traffic between your VPN gateway and your HTTP server will remain clear.

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    That’s my question. When I connect to a Webserver that’s only accessible through that VPN, is that connection encrypted by the vpn? The Webserver that’s hosting the websites is also the VPN gateway – Unkn0wn Jul 19 '19 at 11:34
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    @Unkn0wn accessed through VPN == encrypted by the VPN if the VPN encrypts its traffic. – Andrew Morozko Jul 19 '19 at 11:54

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