New pdf book covers won't show up when transferred to phone?

The new book covers show up on Calibre Companion but when I try to add them to my ebook reader the new covers and metadata only show up on the epub files. The pdf files either don't show a cover at all or it shows the old cover and metadata depending on the ebook reader.

I've been trying for 5 days now to get my new metadata and covers from Calibre from my computer to my phone and I've tried everything and nothing is working. I'm on the verge of an anxiety attack because something so simple shouldn't be this hard. Please don't tell me to try a different ebook reader because I've tried literally all of them. I've also tried all the ways possible of transferring the books from my computer to my phone and ran into a different problem every time.

Converting the pdfs to epub on Calibre makes the books look like trash and on some ebook readers they won't even open or it just freezes the app. So, converting isn't an option. Using the save to disk option and copying them via usb doesn't transfer the new metadata either.

Again, on Calibre Companion all the metadata and covers are correct but when I add the books to any ebook reader it shows the old metadata/covers for pdf files. Or it just shows no cover at all.

:help::help::help::help::help::help::help::help: