There is an often-repeated problem with tracks missing from iTunes playlist imports. The missing tracks are those whose file or folder names in Windows contain accented (or otherwise “strange”) characters, although these tracks do in fact exist in your Plex library. The reason for the tracks being rejected in the import seems to be that Plex (when creating or updating its library) acquires your library track paths directly from the folder/file hierarchy that makes up your music library on your PC, whereas the playlist import gets the relevant path information from the iTunes xml file. This file is encoded in a different character set, so when the Plex importer tries to match the file paths in the xml file with those recorded in the Plex library, the paths containing accented characters will not be found.
The solution to this problem would be for the playlist importer to convert each rejectable file path to the “correct” character set and then try matching again. Sounds simple - but is it? If implemented, it would certainly impress Plex’s international iTunes users.
I have the same issue and eventually wrote a Python script to convert my XML file into a character set that Plex understands. I run that script every time I need to do an import from iTunes (which is multiple times a week!). It has worked well for me, but it would be amazing if Plex itself could take care of this. As it is, it’s essentially a broken feature if you have a track or album with accented characters, let alone foreign characters.
