Outbound Thread Setup

I have an outbound tread that disconnects once a day. I have to stop and start it because I have it setup on the outbound tab  inbound replies to await for replies with setting of -1 for timeout.  I also have the outbound data setup with retries with -1 and interval 15.  I would like some clarification on how does does retries work if I change the await for replies to 10 for timeout.  If the remote system disconnects and reconnects will engine retry the same message over and over until it gets a reply because of the -1 settings on the retries.  If someone could explan how this all works and how it works if the remote device disconnects and how it works if I stop and start the tread.  

Thanks