iBooks & Dropbox

After recently starting the grind through David Foster Wallace’s 1100 page magnum opus Infinite Jest and a new ritual of trying to make it through every edition of the weekly The Economist, I’ve had to start evaluating the reading options that are available to me without carrying around my own body weight in dead trees.

One app that I’ve had a love/hate relationship with for a long time is Apple’s iBooks. iBooks does a great job of handling most ePub’s (unlike the Kindle, which makes a mess of books more often than not), and it’s PDF reader is so good that it’s the only way that I’ll read a PDF anymore. Apple’s even been kind of enough to reduce animation delays for its page flips in recent years, making it suitable for reading books quickly (either that, or advances in chip speed have solved this problem).

iBook’s only weakness is the same as Apple’s: the cloud. There isn’t a good way of getting content into iBooks; your options are:

  • Browse the store from your device and buy or download something from it. This is a slow and frustrating experience at the best of times, and not suitable for transferring other personal content.
  • Plug your device into your computer via USB and transfer content with iTunes. This method involves both wires and iTunes, neither of which is ever going to be a pleasant experience.
  • Transfer content to the device using another program, and use “Open In …” with iBooks.

When using the first option, iBooks may or may not use iCloud to synchronize the content across all your devices, which is a great feature. Unfortunately, this won’t apply to non-purchased content moved using another method.

My current preferred method is to store my books and PDFs in Dropbox from my computer, access them from my Apple devices, and use “Open In …” to move them to iBooks. This of course opens up questions around the edge behavior like, “if I use Dropbox to move the same book onto two different devices, will iCloud sync my reading position between them?” (The answer here turns out to be “yes”, but I don’t know how it matches files, or how reliable that mechanism is.)

It amuses me that if iBooks every does start syncing non-purchased content, any file that I want to read would eventually be bounced between my devices and the cloud like an unbroken rally at Wimbledon:

  1. My computer to Dropbox.
  2. Dropbox to my iPad (where it’s exported to iBooks).
  3. iPad to iCloud.
  4. iCloud to my computer.
  5. iPad to my computer (again) when I plug in the iPad and iTunes starts doing things.

So as seems to happen all too often with modern software ecosystems, I’ve built a patchy routine with a large surface area that works for me today, but which feels overcomplicated compared to my modest goal: reading a book.

Did I make a mistake? Please consider sending a pull request.