iPod classic Gapless Playback

Try putting a CD in , selecting gapless in cd info , then import , thats what I do and it follows over to my ipod

It might not work on tracks done before gapless arrived in itunes
(someone else might know if this is right as I re-did all mine)
I used to rip them as one big track
Then I did them again when gapless was added , nightmare
All I can suggest is 'select all' in library , select gapless and let machine get thru them all
Then send them to ipod again and see

After importing an album, and having set the gap between tracks in iTunes preferences to none, iTunes automatically analyzes each track for gapless playback information. Not all album tracks need it as most have definite end points. Gapless playback is not another way of saying your tracks are now all merged, that's when you use crossfade. Gapless is for albums that have tracks that segue into the next so that you can listen to it as the artist intended you to: Pink Floyd's Dark Side of the Moon, Madonna's Confessions on a Dance Floor, are some examples of where this works well.

OK, so I found the Crossfade playback in iTunes

Also, you appear to be confusing Crossfade with Gapless playback and they are not the same.

Crossfade is an iTunes only feature.

Gapless is backwards compatible with all your old songs, there should be no need to re-rip them.