Local files will sometimes not play on Spotify desktop on shuffle

[Siun]

Plan

Premium

Country

U.S. 

Device

iPhone XS

Operating System

iOS 12, Windows 10

My Question or Issue

Local files play fine on my iPhone Spotify app because it's downloaded so it has a direct file reference, but I have a playlist full of local files that I like to play on my PC and while on shuffle, it will randomly stop playing music and say in blue at the top "Can't play the current song." It will play the exact song if I skip to the next track and manually hit the play button on it, but whenever it's on shuffle, it will just randomly not play certain songs.

I would prefer not having to delete my local files from Spotify because there's several hundred files I already loaded into my playlists and it would just take forever to find which files go where.