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> The bet is that a compromise in both the service and wireguard at the same time is unlikely

An RCE in wireguard would be enough -- no need to compromise both.

I was going to say something like this, but in practice wireguard is very very tiny. It doesn't have pluggable authentication, or passwords, or user transitions, or forked subprocesses, or systemd integrations. Using it or another simple secure transport in front of SSH is probably a good idea.

I don't disagree with you. However, my point was that the parent poster's reasoning was flawed.

Stacking these services on top of each other in this way does not necessarily mean that an attacker has to compromise both services in order to compromise a host. The parent poster's flawed reasoning appeared to lead to a false sense of security as a result.

Yes for sure. An RCE in the first is sufficient, or an auth bypass in the first and some other vulnerability in the second.

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