Windows hosts file only takes first match?

Question

Windows

The question is this, I have a server that is used as dns, the addresses are registered in the
hosts in
the form wi fi clients for them, the address is in 95 networks, and if local clients are in 100 for them . When pinging this address, the site always lies along 1 path to 95.66 and therefore the address does not work for those who have only 100 subnets. Is it possible to fix this by standard means? So that clients with 100 subnets take addresses from the hosts file where the address from the 100 subnet is described, and not by the first match. Hosts file in windows always takes only 1 match?

Answer 1

Everything looks right, I don’t see the filters here (kerio) and there (mikrotik), maybe there is a problem with them.
I would also like to look at the Installed SA at the tick, according to the counters for all the tunnels, it will become clear how they work (symmetrically or not).
Well, in order not to get up twice - export everything on pastebin.com (having cleaned your "white data") from a tick.
According to Kerio - there are not enough screenshots of the firewall rules.