Surprisingly, and oddly (but frustratingly) simple. Granted, I am working with Windows, so I do not know how much variance may be introduced by that, but we share a phone model, so it's not impossible there's some overlap, too. So, I was having this issue last night, both with cover art and song info, and wrestled with my computer for hours to find a solution. (Post edited because I realized the title of the playlist in the last image may and likely does go against the guidelines of this forum lol) Local File Artwork not appearing on phone.