Problem transferring track from Mac to Nuvi 265W

I have been using Garmin Roadtrip for a while but it is not typical Mac software. It is not intuitive and and some things are really confusing.

I have been creating new tracks and transferring them to the Mac and I have been transferring edited tracks and waypoints etc from the Mac to the GPS.

Yesterday I spent all day driving to log roads that are not on the map. They all transferred fine to the Mac were I deleted all the parts that were already on the map. Then to get rid of the clutter I deleted the tracks on the GPS then transferred everything from the Mac back to the GPS. All the waypoints transfered fine but the new track did not transfer back to the GPS.

Can anyone please advise what to do? I spent all day driving to create this track. Now I can see it on the computer but I cannot use it on the GPS.