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I've got a bit of a weird problem, and I'm not sure if I'm trying to fit a square peg through a round hole or if I'm just not sure how to ask the question I really want to ask.

At home, I have a headless server operating as a pihole and wireguard server. On my laptop, I wish to connect to this server and be able to communicate with devices on my home network (such as my desktop PC) as if I were there on the LAN.

The home network is a typical household network: off-the-shelf router provides DHCP service, issuing out IPs at 192.168.1.0/24 with leases starting at 100. My wireguard server is configured to operate as 192.168.2.1 with manually assigned ips in the same subnet, and allowedips are set to 192.168.0.0/16 because I don't want to connect to the internet through my home network, just my home network through the internet.

So far I'm able to communicate with devices connected via wireguard, including the wireguard server itself. What I cannot do is communicate with anything on the 192.168.1.0/24 subnet.

I fear that in order to do what I want to do, I'm going to need to disable the DHCP server in my router and setup my own one on the pihole server which will be able to manage both subnets at once, alternatively I could try simply not doing this seperate subnet stuff and just throw clients onto the DHCP server's subnet and see what happens...

I really don't know what to do here and like I said, I'm not sure if I even know what my question is at this point.

  • Sounds like this is what you want: https://www.procustodibus.com/blog/2020/11/wireguard-point-to-site-config/ -- where Endpoint A in the article is your laptop, and Host β is your headless server. – Justin Ludwig Jul 01 '22 at 02:25

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