I'd suggest saying "Play All" could resolve this issue.

 

yea it does, but it restarts from back at the begining of all your songs.....it's a PITA.

 

I keep shuffle on so when I say "play all" or "play playlist xxx" it will mix it up.

 

My wife has used 2 and 5th gen nanos in her flex with no problems. It is worth a shot to upgrade firmware. I am using the USB2 port with my Ipod.

 

I upgraded my firmware a few weeks afte getting the truck. Unless something has been release in the last 2-3 weeks, I don't think that will helps. I'm using USB2 on mine.

 

Same here. My truck does this with both usb #1 and #2. I use several ipod nano's both 2nd and 4th generation. It won't stick on the same song unless you request artist, but it will do it everytime. I updated sync about 2 months ago with no change.

 

So this seems to only happen to with Apple products?

I only use USB memory sticks in mine, so that maybe why I haven't seen this issue yet.

 

it wouldn't surprise me. I am NEVER buying another craptacular apple product again.