How do you send your plane to a connection-mate? I try sending it to the airport with the connection open, it just sends it to a random person like normal, I can’t find a button to send it to someone anywhere.
Did you tried to start canection?
I mean you helave him in tab “connections”
If you have an active connection to a partner at another airport your aircraft will be send to him. The big question is if your partner handles your aircraft. If he is not online and/or doesn’t handle it within a certain time your aircraft may be handled by another player or it will be handled like an aircraft that you send to any other airport.
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The certain time is in this case 4 hours. Within 4 hours the connection partner can handle it, if not handled in this time, it will go to a random other person and will not count for the streak 
This will not increase the money gain when getting back, so it will indeed count as a “random non-player” airport
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Thanks for the explanation guys