access via VPN subnet... changed?

[Nerdvana]

Hi all - I have a few clients accessing an OpenVPN 2.5.7 instance (hosted on an Ubuntu droplet at DigitalOcean). Clients are either OpenVPN 2.5.2 on OpenWrt or OpenVPN Connect 3.3.5 on MacOS or iOS.

The VPN subnet is 10.8.8.0/24. Up until late September all clients could access the server on 10.8.8.1, as expected. That has recently stopped working. I don't *think* I made any server config changes (and have reverted server.conf to be sure) but I have been installing all the OS upgrades.

Bizarrely (IMHO) the OpenVPN Connect client on MacOS can access the server on 10.8.8.0, but not on 10.8.8.1. I don't understand this AT ALL.

The primary purpose of this VPN is client-to-client networking, which continues to work as normal.

Does this sound familiar to anybody? Any and all suggestions welcome.

Cheers
Sean

[TinCanTech]

can access the server on 10.8.8.0, but not on 10.8.8.1. I don't understand this AT ALL.

That is highly unlikely..

[Nerdvana]

Agreed that it's highly unlikely, but here we are. See below, especially the bash environment variables:

Code: Select all

sean@Sean-MBP ~ % ssh 10.8.8.0
Welcome to Ubuntu 21.10 (GNU/Linux 5.13.0-52-generic x86_64)

2 updates can be applied immediately.
To see these additional updates run: apt list --upgradable

Last login: Sun Oct  9 20:26:28 2022 from 10.8.8.16
sean@HHGorilla:~$ env|grep SSH
SSH_CONNECTION=10.8.8.16 54813 10.8.8.0 22
SSH_CLIENT=10.8.8.16 54813 22
SSH_TTY=/dev/pts/0
sean@HHGorilla:~$ 

Cheers
Sean

[TinCanTech]

So, what you are trying to say is:

You have configured Openvpn in such a way that your ssh server is now functioning on the network address ?

[ordex]

Maybe the server log could shed some lights?