Hi there. Here's
how to check what your import settings are in iTunes. You can get information about a track in iTunes, by right-clicking and selecting "Get info."
Playlists not synching correctly does come up from time to time, this is partly down to the way iTunes works and the way Sonos reads playlists.
If you playlists are not being reflected correctly in Sonos, you will need to check (and possibly recreate) the ".xml file" for your iTunes library. The .xml file is an Apple proprietary file that tells third-party applications which tracks belong with which in a playlist. It can be compromised by dragging and dropping library items between your folders, or migrating files from one computer (or directory) to another. If this has been compromised, playlists do not work or update correctly and so you will need to "consolidate your library". This will make a fresh copy of the .xml file. Yes, unfortunately the .xml file really
can be that sensitive.
You will need to find the .xml file in your folders. It would typically be in the iTunes folder itself, (C:\users\myname\music\iTunes). If it is not, or if the modified date is incorrect, this is why your playlists don't work. If you find the .xml file elsewhere and the modified date is correct (i.e. it coincides with the last time you used iTunes) you can try simply dragging it into C:\users\myname\music\iTunes and reindexing your music library within Sonos. However, if you can't find it, or if the date is wrong, I recommend doing a websearch for more information on .xml files and iTunes library consolidation.
If any of this is unclear, it would be best to contact Apple support. If you find the .xml file and it appears to be correct, please report back.