I haven't been able to work out when Wi-Fi Sync was introduced, so you'll have to look for it in the Settings (on the iPod). I will give it a try, if my iPod Touch has that functionality. The first time I started seeing those dashed circles (which I understand means "this song is not actually here") was right after I updated iTunes. however each of the new songs has a dashed circle in front of it. However, after the syncing operation (which takes a very long time for some reason), the list of songs that is displayed within iTunes as the songs on the connected iPod device, do include the new songs. In all cases, the new material (new playlists, new songs) that are not already on the iPod, do not show up on the actual iPod. various other alterations, like recoding in AAC or lower bitrate.syncing individual songs in the playlists.In addition, in the perhaps 50 times I've tried to sync unsuccessfully in the past week, the 5 steps it goes thru are always mentioned, but no files are transferred. I also spent one hour with an Apple Support person (for which I give her thanks) and we reviewed all sync-ing options. and the playlists transfer on iPhone and iPad, but not iPod. Well, I've set the sync options the same for all devices. I can tell you though, that the same problem exists with a similar programme to iTunes, that is used for synchronising music to Android devices, and that is fixed by using a wireless (Wi-Fi) sync. I have no idea why cable sync doesn't work correctly anymore. check the suggestion about erratic syncing by fellow user turingtest2, in this discussion: I can transfer a playlist from iTunes to … - Apple Community (it's the reply to the original question that you want to look at).try a Wi-Fi Sync (or, if you're already using Wi-Fi to synchronise your device).I have recently begun using Wi-Fi Sync to manage my iPod and that seems to produce much better results. There has been a long-term issue with erratic syncing, which Apple have yet to fix. The issue is that for some unknown reason, some songs have not been added to the iPod (or have been removed) and are now listed as phantom songs. I have experienced myself and it's infuriating. Ah, the infamous dotted circle, I get it now.
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