It may have been an issue with that iOS version, or the conversion program itself.
Ultimately, however, now that iOS 14 will be released this year, this question is largely unnecessary in 2020 and beyond.
I’m sorry; I don’t know any free apps, but I can suggest two paid apps, if that’s any use.
There’s an app called Audiobook Wizard that I used a year or so ago, under Snow Leopard, that seemed reasonably fast and easy to use.
However, it’s a paid app ($4.99) offered through the Mac App Store: http://itunes.apple.com/us/app/audiobook-wizard/id460967298?mt=12. This is apparently Lion compatible and a decent audiobook editor. I haven’t tested this version though.
The developer also offers a free version, which can be downloaded from his site: http://www.audiobookwizard.com/. This only supports Snow Leopard and below, because it has PowerPC components, but you might like to download it to get a feel for the app.
There’s also Audiobook Builder. Again, this is a paid app ($5.99) in the Mac App Store: http://itunes.apple.com/us/app/audiobook-builder/id406226796?mt=12. I haven’t used this before, and I’m not sure if it’s Lion compatible. A cursory search of the forums on the developer’s website doesn’t find any problems, so it might be ok. Might be worth trying; not sure.
You’re right about .m4a
and .m4b
files. This isn’t so much a problem with iTunes, as the file types. .m4b
files have the capacity to “bookmark” parts of the file that .m4a
doesn’t. From the Wikipedia page on MPEG-4 Part 14:
Audio book and podcast files, which also contain metadata including chapter markers, images, and hyperlinks, can use the extension .m4a
, but more commonly use the .m4b
extension. An .m4a
audio file cannot "bookmark" (remember the last listening spot), whereas .m4b
extension files can.
Best Answer
I think your issue is your file type, audiobooks are usually MP3 files. MP3 files can only be used for audio, whereas MP4 files can store audio, video, still images, subtitles, and text. In technical terms, MP3 is an “audio coding” format while MP4 is a “digital multimedia container” format.
After changing file format, try importing into iTunes again and syncing the files to your iPhone via USB.