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Highest I have seen even towing was 212F and it didn't stay there very long. It always seems to settle in around 201-205F after a long drive no matter if I'm towing or not. These liquid-liquid heat exchangers are very nice and help to maintain a very consistent temperature and performance over a variety of conditions. My only issue is that when driving empty in the winter it seems to take almost an hour to get the Trans up to temp, but I suppose there is a ton of fluid to warm up.
Also, learned recently that the 6.2L gas SD trucks actually use a air-liquid heat exchanger and those guys report a much larger range of temperature operation. Another great reason to get the diesel!
I have found the voice to be the best part of the new sync. I really like it.
If you are ever lost, just say "what can I say" and the screen will display a list of commands.
Also be sure to update your software if it wasn't done at the dealer. The latest update is really nice.
Probably doesn't belong on this forum, but do you know when the latest SYNC update was released? I updated mine in August of 2013, didn't know if there is a newer one for the MY2014 trucks but according to the Ford site my MY2013 has the most recent update.