Rescuing Photos from an iPhone

Note: I've updated the workflow, after receiving feedback about a Lightroom-related idiosyncrasy.


I started college in 2007, only a couple of months after Steve Jobs announced the iPhone. I had a Canon 20D, which I used over the next four years to document everything from mundane social outings to the occasional on-campus protest.

In 2012, there was a regime change: I bought an iPhone 5. Unlike a DSLR (I now have a Canon 60D), it has the capacity to geotag and automatically upload photos via Wi-Fi or LTE. Optics- and software-wise, its camera is more than adequate for my casual-photography needs. Most important, I feel comfortable using it to take photos in public. In the late 2000s, it wasn't a big deal, lugging around my 20D; now I feel like a Glasshole if I take photos with anything that conspicuous.

The problem is, there aren't any reliable, standardized methods for backing up and managing iPhone media. (I'm sorry, but iPhoto doesn't cut it.) And with Apple still selling iPhones with only 16 GB — even 8 GB — of storage, this issue is only going to get worse. Certain podcasts like Accidental Tech Podcast and The Prompt have dedicated entire episodes addressing the issue. Below, I've outlined my own attempt at managing iPhone media.


UPDATE May 11, 2014: My dad discovered a bug with the workflow, as previously described. Instead of initially enabling Camera Upload in Dropbox on iOS, you should first set up the workflow in Lightroom. Otherwise, this is what happens: 

When I tried to navigate to the Dropbox photos with the uploaded iPhone pics in it, I got an error from Lightroom — something like: ‘You must pick a folder that is empty. This one is full of photos, idiot. Start again and pick another folder that is empty.’

I paraphrase. So I had to empty the Dropbox Camera Uploads folder in order to get Lightroom to link to it.

The Workflow

I discovered an automated photo-import workflow that uses a combination of Dropbox's Camera Upload tool and Lightroom's ability to automatically import files. First, open Lightroom.app. Click File > Auto Import > Auto Import Settings…

In the Auto Import Settings window, you can specify several powerful settings:

  • Choose your target folder (i.e., "Watched Folder"). This allows Lightroom to automatically import photos from any folder. You'll want to navigate to Dropbox's Camera Uploads folder, which you can generally find at ~/Dropbox/Camera Uploads.
  • Choose your destination folder. Lightroom will take photos from "Watched Folder" and import them into a location of your choosing. In this case, I've decided to place all iPhone photos in their own folder at ~/Pictures/iPhone.
  • Customize file naming. This is where Lightroom's Auto Import tool is most powerful. When Lightroom imports your photos, it can automatically rename them. I like to name my photos with a "Date" field first, followed by a piece of context, like "iPhone." You should also append an "Image/Sequence Number" field. That way, when Lightroom imports photos to your destination folder, it renames them sequentially, in the order in which they were originally taken.

Next, Enable "Camera Upload" in Dropbox on iOS. I've heard some people complain that Camera Upload is a sneaky way for Dropbox to force users to upgrade to a higher-tier storage plan. With this workflow, Lightroom automatically depopulates the Camera Uploads folder, so you can use Dropbox's standard 2 GB plan without running into storage limits.


The Downsides

While this workflow is a powerful tool, it has a couple of downsides:

  • Changing the Destination Folder is a pain. My Mac has a 250 GB SSD, which is enough space for my photos. But that won't be enough storage in the near-future, so I'm already considering offloading photos to an external hard drive. When I first discovered this workflow, I changed the location of the destination folder — that was a mistake. I had to dig into the Auto Import Settings window and reconfigure all of those original settings. And many of the photos' names were out of order, so I had to rename the files in Lightroom. (That's easy to fix: Select the photos and press Fn + F2 to batch rename, so the images are once again listed sequentially.)
  • The workflow is mostly automatic… mostly. Thanks to "Background Uploading," Dropbox on iOS automatically imports photos taken on an iPhone into the Camera Uploads folder on your computer. But the workflow won't continue unless Lightroom.app is open. The photos will sit in that Dropbox folder, instead of going to your destination folder.
  • It feels like a stopgag. In an ideal world, everybody would be able to access every photo he or she has taken, and the media would automatically sync across all devices. But until companies like Apple are able to solve the scaling problem of syncing and backing up every photo every user has taken on hundreds of millions of devices, we're left to fend for ourselves.