@pmbauer Thanks. True, I’d considered that as well. But, I don’t use that “optimize” feature:

Not to say there might not be a bug on Apple’s end (I’ve had my fair share of iCloud problems over the years). When I check right now, all of my files say “Downloaded” though.

I also have a bash script that periodically checks the iCloud database (directly via SQLite) for “stuck” items (you can see these with brctl status also) and reports those errors to me. So I try to stay on top of iCloud shenanigans.
Bigger picture I’m thinking as my vault gets larger and more important, that my best move will be switching to Obsidian Sync and/or a git repo combined with a periodic 1-way sync up to iCloud to be able to view on mobile.