The developers of that software even go as far as telling you that a wireless (Wi-Fi) sync will be more reliable. I'm not convinced that it's a cable issue because I've used different cables (including an expensive high quality one) and as stated, the same issue (incomplete syncing when using a cable) arises with a certain piece of software intended for Android devices. If you can try it, you have nothing to lose. The Wi-Fi option is easier, although I admit that at this stage it is still a test to see whether it resolves the issue (I'm satisfied so far). Gulp, I'm not sure I want to go the route of tt2 yet If you have iOS 9 on your iPod, that suggests a 5th generation model. On a 6th gen Touch, it's in Settings /General / iTunes Wi-Fi Sync. 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. I have a 5th gen iPod, now called classic (no such tag when purchased), 80 GB, software version 1.1.2 and it works fine with iTunes version 12.10.1.4 running on Windows 10 Home 64-bit version 1903 OS build 18362.418, and has never stopped working through all the iTunes and Windows upgrades/changes since iPod was bought more than a decade ago. 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.
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