Sideloading audiobooks to an iPhone
I released an audiobook a few weeks ago, the first time I had done so. This was the counterpart to the print and ebook editions of Six Centuries of Type & Printing, a work that explores the evolution of printing technology. I used Adobe Audition to record and edit, as well as insert markers that would be exported to serve as chapters. Steven Schapansky, a beloved member of The Incomparable team and excellent audio engineer, took on the audio clean-up and production for me.
This is where we hit the first snag. Steven exported the audio as MP3, and Apple’s Books app for Mac read the chapter markers but seemed to think they were zero seconds long. A little research on my part found that “chapterized” audio files, ones with chapter breaks, can work with MP3, but most apps handle this better with the newer-but-not-at-all-new AAC format (part of MP4). So I exported to AAC, which uses the .m4a extension by default, tested it with Books, and thought all was good.
But there I hit several snags, after a reader let me know they couldn’t get the audiobook loaded and synced to their iPhone:
- Books for Mac didn’t allow importing the file in all the ways that Books allow.
- Importing the file into Books with iCloud syncing enabled for Books (on all my devices) didn’t make it accessible on my iPhone or iPad in the Books app.
- Opening the File in the Files app on an iPhone or iPad only lets me play it within Files as a native audio file. I was unable to import it into Books.
Through some trial and error, as well as more careful reading, I uncovered some useful tidbits that helped me solve the problem, and I think they will be useful if you’re ever faced with an audiobook you want to load.
The right format
For starters, I should have read slightly more deeply about audiobook formats. The sucker that I am, I thought audio was a solved problem, and it just works. D’oh! If I had, I would have discovered that the .m4a (with an ‘a’) and the .m4b (with a ‘b’) formats are absolutely identical except for the file extension, yet .m4a is treated like an audio file and .m4b like an audiobook with chapters.
Simply changing the extension with no other conversion allowed me to double-click the file and have it open in Books. I could drag the file onto the Books icon in the Dock or into the Books app to the same effect.
That solved one problem, but the file still didn’t sync to iOS/iPadOS Books. That required a journey into the wilderness of Finder-based synchronization, something I thought we’d mostly shed except for very particular purposes. Turns out, audiobooks are one of those.
Weird-ass Finder audiobook sync
Before iCloud sync, we had to do a lot of messing about in iTunes and later the Finder to synchronize our various desktop and mobile data. iCloud took the fuss out, even though it could be frustrating to troubleshoot when something went wrong. I have rarely touched Finder-based sync in years.
iCloud sync does not apply to audiobooks you import into Books for Mac, only ebooks, generally in EPUB or PDF format. Audiobooks you purchased from Apple’s Bookstore sync just fine, as do all other pieces of purchased or rented digital media.
So you have to use the Finder interface—that’s where Apple directed me to go. For as little as Apple likes the idea of sideloading apps, it loves sideloading media: the iTunes/Finder iPhone/iPad interface is mostly about choosing what media files from a Mac (or a Windows system) get synced for access by the appropriate iOS/iPadOS app. Audiobooks is one of them.
Be warned, however: Overriding the current sync settings will sever your connection with any previous choice you’ve made for syncing local media for Apple’s categories of Movies, TV, Podcasts, and Books. Music, Books, and Info can be affected if you aren’t using iCloud syncing.
To sync your audiobooks, follow these steps:
- Connect your iPhone or iPad to a Mac1 unless you’ve already connected and enabled Wi-Fi syncing in the past, in which case you can skip this step.
- Select your device in the Finder sidebar.
- Click the Audiobooks tab.
- Check the “Sync audiobooks onto [device name]” box.
- If you had previously synced with another library, you’re warned this will break the sync. Click Remove & Sync.
6. Make your selection of audiobooks.
7. Click Apply.
8. You’re warned again with more specifics about the library replacement: which library that’s in use will be replaced with the one from this Mac (or Windows device). Click Sync and Replace to proceed.
Your audiobooks finally show up on your iPhone or iPad. You must repeat this operation every time you load more audiobooks onto your Mac. Seems rather outdated.
Podcast apps might be superior in this regard
You know where else you find sideloading? In podcast apps. Because not all podcasts or audio files you want to listen to in a podcast app can be retrieved via an RSS feed, many apps allow you to import episodes and audiobooks. That’s often a premium feature.
In Overcast, for instance, you need a subscription ($10/year, removes ads and offers 48-hour undelete among other features) and gain access to 10 GB of file upload space, 1 GB maximum per file. Castro‘s Castro Plus subscription ($24.99/year, many extra features) lets you drag files into the iCloud Drive > Castro > Sideloads and have them appear as soon as they sync within the app.
[Got a question for the column? You can email glenn@sixcolors.com or use /glenn in our subscriber-only Discord community.]
- You can also sync using Windows. ↩
[Glenn Fleishman is a printing and comics historian, Jeopardy champion, and serial Kickstarterer. His latest books are Six Centuries of Type & Printing (Aperiodical LLC) and How Comics Are Made (Andrews McMeel Publishing).]
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