Local Files Won't Play On Android

[GoodnightSleep]

Plan

Premium

Country

USA

Device

Android LG 

Operating System

Windows

My Question or Issue

Hi! I've been using Spotify on my phone for years, and I have Premium. Until now, local files that I put on my computer transferred over to my phone just fine after connecting the two to the wifi at the same time. I just bought a new computer (moved from Mac to PC) and the local files from the old computer held over until today, when I synced with the new computer. 

I expected the old files to not carry over, since I haven't brought them over from the old Mac computer. My problem is that a new local file that I have on my new PC isn't downloading onto my phone at all, no matter what I do, which worries me. I tried every solution, but it's not working. What can I do? And will bringing those old files over mean I can re-upload them to my phone?

An extra note: my desktop said it had an update and needed me to restart my computer, and I think it did so. Is there a new update that might have interfered with this? Thank you!