PDFs aren't syncing between devices or showing up at all

What I’m trying to do

Pdfs in the same vault are visible and functional on iPad but not on Macbook. Would like to see pdfs on Macbook.

Things I have tried

I added pdfs from my Macbook to my Obsidian vault. The pdfs are in the same folder as the Obsidian text files and I can see them all in the appropriate folder in Finder. Next time I open it, the pdfs are gone. However, the pdfs are there and fully functional in my vault on my iPad. I have the Sync plan and I flattened the pdfs to be as small as possible. I am using a very small amount of my Sync plan storage. Obsidian says the vault is fully synced and my text edits are showing up and syncing as normal in both places.

What are your sync settings? Are both devices set up to sync pdf files?

Having a similar issue, setting up some notes for a class this week, have a pdf handout that I added to a file on my Windows desktop (Obs ver 1.8.9) and have it set up looking at it now in split with a note that I can use for the class, but on my ipad (also Obs ver 1.8.9) it doesn’t exist. Using Ob sync, and I can change the note itself and it automatically shows on Windows. On desktop, I dragged the pdf into the note itself which shows up ok, but on the ipad it creates a link on the ipad which states “Could not be found”. Any ideas anyone?

What size are your PDFs? Isn’t there a file size limit on any given single file in the sync plan?