My music doesn't play, shows 'waiting' with a dotted cloud icon
I reinstalled Catalina on Friday (15th) so I had a factory fresh Mac.
I have a Late 2015, 1.6 GHz Dual-Core Intel Core i5
I'm trying to Populate itunes from my external hard drive, usually when I do that it'll work. Now, it'll go through the motions of adding the files but not actually add them.
When I'm signing into my Apple Music account the files population, but they're all greyed out (other than like a dozen, which are able to be played). The greyed out files having 'waiting' along with a dotted cloud icon next to it. I've left my machine on overnight, hoping they'd upload but so far, nothing
I've had sync activated across all my devices, I've signed out of them all so that only my Mac remains.
File > Library > Update Cloud Library doesn't seem to do anything. I don't get it
Any suggestions on what to do?
I'm at a loss as to what to do next.
iMac Line (2012 and Later)