http://stackoverflow.com/questions/38917902/akka-net-remote-between-linux-and-windows

Pretty sure this is the issue (repeating my SO answer):

The issue here appears to be that Mono is using an IPV6 address mapped to IPV4 in its bound address for some reason.

akka://TestSystem/system/transports/akkaprotocolmanager.tcp.0/akkaProtocol-tcp%3A%2F%2FTestSystem%40%5B%3A%3Affff%3A192.168.0.252%5D%3A36983-1

If you decode this URL that gets translated to

akkaProtocol-tcp://TestSystem@[::ffff:192.168.0.252]:36983-

So I think what is happening here is that outbound address Helios is supposed to parse from that is getting screwed up on the Linux side, so it attempts to connect to a mal-formed address that isn't the same as the one Windows listens on. Something platform-specific in the actor selection URI parsing code is incorrect I suspect.