Who Me Too'd this topic

I have been having this extremely frustrating issue on my iPhone 5s where I cannot get some local files to sync no matter what. My iPhone shows up under "Devices" in my desktop client, and I have thrown all my local files into a new playlist which I have marked for offline access, but every time I try to sync them again, the same files will not sync no matter what. I've attached screenshots of what my playlist looks like and what my device looks like in my computer. The status of the syncing playlist is always stuck on "Pending", and I haven't been able to find any solutions here on the forum. It's weird to me that the same files won't sync no matter what, and I have enough space on my phone. Also, when I unmark the playlist and then mark the playlist for online access again, my phone and computer display that the files are beginning to sync again temporarily, but then revert back to "Pending" status. Is there a maximum number of local files one can sync?