Q: 160 GB wont sync...
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Sep 5, 2016 3:37 PMby Kenichi Watanabe,HelpfulThat is normal, if iTunes does not have any updates to sync to iPod. Are you saying you expect changes (such as new songs) to sync automatically to iPod, but they do not? If so, you should check how the iPod's Music settings screen is set up in iTunes. If it's not currently set to sync music, the iPod still shows that it's "syncing" (when connected) but nothing syncs. It does what you described.
Click iPod's device button in iTunes. The screenshot below shows upper left corner of my iTunes window, with device button circled in red.
The iPod's Summary settings screen appears. Along left side of window, in the sidebar, under Settings, click Music. The iPod's Music settings screen appears to the right, where you tell iTunes how to sync songs to iPod. Checkmark the box for Sync Music.
NOTE: If this box is not already checked, and you check it now, any songs on iPod that are not in your computer's iTunes library will be lost.
This turns ON automatic syncing. Below that, if your music library can fit on your iPod, you can choose to sync Entire music library. Otherwise, you can choose to sync Selected playlists, artists, albums and genres, and make selections from the lists below. Click Apply. Going forward, iTunes automatically updates iPod when you connect it (or click Sync if already connected), based on how you set up this screen.
If this is not the problem, please post back with more details about your situation.
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Sep 5, 2016 3:43 PMby Dustin Dirt,Thank you so much for taking the time to answer my question. Sync is checked, all those steps are covered....A little box pops up and says something like certain files wont sync because they could not be found.....and there are 100+ files with this problem......but I have thousands of songs to sync...so this cant be the only problem. I download my music for free off of SoulSeek and I dont pay apple a dime for any music......could this be part of the problem? Thanks again for your time. I never expect anybody to reply.
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Sep 5, 2016 3:50 PMby Kenichi Watanabe,No, iTunes does not care about the source of your song files. They can be purchased from iTunes Store, imported from music CD, or added manually to iTunes library.
Are you able to play your songs in iTunes? Try to play one of the songs listed as not able to sync. If it won't play, do a Get Info on the song in iTunes (right-click song and Get Info). In Info window File tab, what does it say for location? That is where iTunes expects to find the song's file.
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Sep 6, 2016 9:16 AMby mtbarone,Are you running iTunes 12 on Windows 10? If so, see my post above. According to an Apple tech, they decided to no longer support the iPod Classic so you will never be able to sync. I don't know if enough pressure from the community could change their minds but this whole issue is flying way below the radar.
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Sep 6, 2016 9:55 AMby lonewolf3898,Same thing happens to me, regarding the pop-up and the 100+ files thing... that's simply saying that the songs already on the iPod can't be re-synced, since they cannot be found on your computer at the time of the sync. With me, after I sync (add or remove) songs to/from my iPod, I move them to an external HD for safe keeping, so of course the iPod can't locate them when syncing. Your iPod is essentially saying "hey, I can't find all these other songs currently on the iPod, so I can't do anything with them." Not to worry.
