This morning I was dealing with the 1965 edition of the Grinnell College yearbook, Cyclone 1965, in Digital.Grinnell. That's a monster of a yearbook, 278 pages and a .pdf that's almost 1.4 GB in size.
In order to get the .pdf to upload I tried a number of tricks, the only one that worked was a modification of Book Ingest in Digital.Grinnell The key command was...

docker cp "/mnt/storage/Yearbooks/Cyclone 1965/lib_1965cycloneyearbook_0002.pdf" isle-apache-dg:/var/www/sites/default/files/book.pdf