iTunes Digital Booklets associated with Music Albums cannot be found

See the support article Hide and unhide music, movies, TV shows, audiobooks, and books - Apple Support and check for any hidden purchases. While past purchases are generally available for redownload this may depend on the content still being available in the store. It is possible some of these have been withdrawn. Ideally you would download and backup all of your purchases just in case.

tt2

That is likely the issue then. You can reach out to Official Apple Support but I suspect there is nothing they can do to restore withdrawn content.

tt2

So I have 8 digital booklets that show up with cloud download symbols as they are not currently downloaded to this library. Presumably if I downloaded each of them they would all work as expected. The one for David Bowie's Blackstar works. I don't know if I had more in the past. I know my other big library includes a few PDFs attached as digital booklets from sources other than iTunes. You might create a new empty library and see if that shows a cloud link for the one you find is corrupted. If so you could download it, and then copy it over the bad file.

tt2

Does the version of the album currently in the iTunes Store include a Digital Booklet?

tt2