Hi - NM - I found it. Turns out that I was a flake… yeah pebkac, I know. Solution: I had migrated this site from another server long ago and didn’t realize that I neglected to modify the uploads path. I assumed this was the result of the most recent update, but alas, no, silly me.
Go to: Settings --> Media --> Store Media in this folder and there put the FULL PATH of your uploads, which on Galactus , for example, is /home/username/domain.tld/wp-content/uploads
If you copied the files up via FTP, you may also need to recursively change file/folder permissions. It’ll generally only impact you if you backdate posts (like if I edit a post from October 2010, it’ll put the image in /uploads/2010/10/ no matter what day today is).