Wireless, Cross-device, photo syncing in 2015

Once again I'm visiting my work flow for syncing photos wirelessly from my phone, to my computer and back to the phone. I have blogged about this a few times in the past. In my last blog post regarding photo sync, I had turned to Lightroom mobile. It worked well for photos, but lacked any kind of support for videos.

A lot has changed over the last year. Now both Apple and Google provide bi-directional, wireless, sync of both photos and videos to and from your mobile devices, while keeping originals synced on your desktop computer and stored in the cloud. Take a photo or record a video on your device, open your computer to edit it, view the changes later in the day on your phone. It's pretty slick.

Now that both companies support sync in this manor, I thought I'd go over my workflow. The changes in the way both services handle the sync have caused me to change my work flow a bit. Since I use iOS and OS X devices most, I will be writing about Apples services today. At some point in the future I'll try and write something up on using Google Photos + Google Drive on Macs and iOS for cross-device syncing of photos and videos.

iCloud Photo Library

In 2014 Apple introduced the new iCloud Photo Library and Photos app in iOS 8. The iCloud Photo Library handles synchronizing all of your full resolution photos and videos across every iOS and OS X based device you own. Unfortunately, this is not available on AppleTV.

So, we need to turn on iCloud Photo Library on the iOS devices. You can do that by going into the iOS Settings app and navigating to Photos & Camera.

I typically leave my iOS devices with Optimize iPhone Storage enabled. This will upload the original files to the iCloud Photo Library; saving a reduce size version for the smaller iOS screens on the device. In some cases, it will remove the photo all together and leave a thumbnail. The next time you view the photo, it will download it again. I've only seen this happen on old photos, or when re-installing iOS fresh.

When you make this change you will notice that the Camera Roll is no longer available. Instead it is replaced with All Photos. That is because the photos are no longer stored on-device. Now they are stored in a shared library with multiple iOS devices, which requires more than what the original Camera Roll provided.

Now that we have iCloud Photo Library setup on your iOS devices to upload all of their photos and movies, we need to setup OS X. The Mac works much the same as iOS. You open up the Photos app (requires Yosemite or newer) and open up it's preferences. The only difference is that we want to tell the app to download all of the originals onto our Mac's hard-drive. This way, we always have our originals locally and aren't depending on the cloud keeping them forever.

Now we have all of our photos (and videos!) synchronizing wireless between our iOS devices and the Mac.

iCloud Photo Library to Lightroom

So we now have our photos and videos locally on our internal or external hard-drives. What do we do with them then? We export them from iCloud Photo Library and move them into Lightroom! I use Lightroom to handle all of my keywording and orginization of my photos and videos. The new OS X based Photos app fully supports keywording and organizing into albums and folders. It does have some issues, like not being able to move an album in and out of folders once the album is created. Keywords will sync across all of your devices, but the folder/album organization will not. Albums are only synced to iOS in a flattened layout, with no nested folders. An example of this on iOS looks like the following screenshot, where all of the years are flattened out.

As a result of this, I will continue to use Lightroom for my photo organization. I keep Lightroom as my source of truth, where all of my originals will always live. In Lightroom, they are organized like this:

So how do I get my photos from the OS X Photos app into Lightroom? I use a Smart Album in the Photos app! With Smart Albums, I can keep track of what date I last pulled photos into my Lightroom library. There are two Smart Albums I create. One that filters all photos that I have already brought into my Lightroom library, and a second that filters all photos that I have yet to export from Photos, and import into Lightroom.

So before we create our Smart Albums, we must first actually export the photos from iCloud Photo Library and get them into Lightroom. When I first turned on iCloud Photo Library, I had to wait just a little over 24 hours while it got all of the photos synchornized across the devices and downloaded onto my Mac. Your mileage will vary, depending on how many you have. You can see in the Photos preferences picture above, that it tells me my Photos library was just updated. That means I am in sync and nothing is outstanding. During a first time sync, it will count down how many photos and/or videos it has remaining to download onto your Mac.

So, if your sync is done, select the Photos library

Next you will need to select every photo in that library. You can do this with Command+A or using the Edit menu.

Lastly, we will export the selected photos from the Photos app, so that we can import them into Lightroom. Note that exporting will not remove them from iCloud Photo Library. It will instead create a copy of every photo and place the copy in the desired export folder. This is ideal, so that we can continue to view the photos and videos on our devices without any issue.

You can set some settings on your photos prior to the export taking place. I typically use the following settings for my exports.

Clicking the Export button will prompt you with where you want to store the files. You can store them anywhere for now. When we do the import into Lightroom, the Lightroom application will move them into their final resting place within your Lightroom library. So just pick a temporary location for now.

Now that the photos and videos have been exported, we need to get them into Lightroom. We can do that by opening Lightroom and doing an import.

On the left-hand side of the Lightroom import screen is the source of the files you want to bring into Lightroom. You will navigate to your temporary folder that holds your exported iCloud Photos. On the right-hand side you will select where your Lightroom library is, this will be their permanent storage location.

Now your photos are all set in Lightroom. You can go ahead and organize them, keyword them and edit them as you want. Next, make a back up of your Lightroom library! It's always good to keep a back up of your photos elsewhere once you have them all imported. Lightroom handles backups automatically for you when ever you close the app.

Once you are done organizing and keywording all of your photos and videos, go ahead and select them all in iCloud Photo Library and delete them. Once they are deleted, you will drag and drop all of the photos from Lightroom, into iCloud Photo Library. This will sync all of the keywords, meta-data, and edits made to your photos on to all of your devices.

Now you have your photos in sync across all devices. The first time you do this, it will take a bit. If you do this every couple of weeks, it won't be to much of a hastle. Let's cover how to do that now, using the Smart Albums I mentioned earlier!

Smart Albums

We will create a new Smart Album that will keep track of what photos and videos you have already imported and processed into Lightroom, and brought back into the iCloud Photo Library. A second Smart Album keeps track of what photos and videos are in your iCloud Photo Library, but not in Lightroom. These are going to be handled simply by tracking dates.

The first smart album is called "Importing - Pending", meaning these photos and videos are pending the import process into our master Lightroom library. You could call it something else, like "Need exporting" if you want.

This Smart Album will show me all of the photos and videos I need to export from iCloud Photo Library, and import into Lightroom. The nice part of using a Smart Album like this, is that now I know all of the photos I need to delete, and re-upload once I am done organizing my stuff in Lightroom. I can open this Smart Album, select all of the photos and videos, delete them, then drag and drop my stuff from Lightroom back into iCloud Photo Library. I set the date to be the date that I exported all of those photos.

The next Smart Album is what we will use to track what has already been imported into our Lightroom library. This will be called "Importing - Processed" and will have a date set to the day of the day you exported your photos. There might be some overlap when you next do some importing, but that's alright. Lightroom does a good job of detecting duplicate photos and show which ones it thinks are duplicates and won't import. Worse case, you have to review each photo for that one day. That's typically not many photos and videos and is worth the extra step to make sure you don't miss any.

Another option would be to add a keyword to every photo in your Lightroom library with a Lightroom keyword. Then you can create Smart Albums that look for that keyword. This way, new photos will lack it and can be added. The only downside is that keywords can't be applied to videos, which is why I chose not to go that route.

Now you have everything you need to keep both Photos and videos in sync across every single device, while maintaining the original, full-resolution, files on your local computer. By adding keywords correctly, you can do full searches in iOS and find photos really fast. As an example, I performed a search in my iCloud Photo Library (with nearly 9,000 files) on iOS for photos of an old car I had 8 years ago. The search results came back instantaneously.

Proper keywording of your photos in Lightroom (or in iCloud Photo Library if you don't want to use Lightroom) can really make it easy to find your photos.

Why Lightroom?

I used Lightroom in this example just because it is the photo suite that I use. The entire section based on Lightroom can be applied to the old iPhoto app or Aperture. If you want to keep your photos in iCloud Photo Library, you can do all the keywording within that app and not both with the whole export/import process. Instead just build smart albums that have look for a "processed" keyword, and add that keyword to every photo you process in iCloud Photo Library directly.


Sadly, the new iCloud Photo Library is not supported by the current generation of AppleTV. I'm not sure why, other than the fact that storage on the device might be an issue (iCloud Photo Library includes videos, where Photostream does not). I'm not sure, so for the time being when you have visitors, you'll need to Airplay your photos to your TV from an iOS device or from your Mac.

Another option could be to use the Flickr app. I have not used the app personally, so I'm not sure what options it has. The app does exist on AppleTV and you can upload every photo in your Lightroom library up to Flickr for viewing on the AppleTV.

I'm hoping I'll be able to revise this post once the new AppleTV is released, with a guide on viewing the iCloud Photo Library on it. There's no official word yet that it will be supported.