Wireless, Cross-device, photo syncing in 2014

For the last two years I have used Aperture for storing, organizing and sharing our photos. It wasn't the perfect photo solution, which I've blogged about more than once, when it came to wirelessly getting photos from several devices in to the Aperture library. I did however like how much flexibility it provided me for organization. I know that Lightroom had really good organizational features, but it didn't play well with my iOS devices and Photostream wasn't supported, which made wirelessly uploading my photo's impossible at the time.

The stars have since aligned, with Aperture being discontinued and Adobe releasing Lightroom for iOS, I now have the opportunity to move over to Lightroom and actually end up with a much better solution. After getting all settled in with Lightroom, I am now able to take a picture on my iPhone, open Lightroom on my iPad and make edits, then open up Lightroom on my Mac or Windows PC and have the original photo and it's edits already ready for me to add keywords to and organize. Even better yet, is that my wife's iPhone has Lightroom on it, and every picture she takes, shows up on both of my iOS devices and on our two computers, without any issues. Well worth the $10 a month it's costing, plus I get Photoshop for my machines and iOS devices, so it's a great value for the price.

The setup

I downloaded and installed Lightroom mobile on my iPhone and my two iPads. Then I downloaded and installed Lightroom mobile on my wife's iPhone and her iPad. Finally, I downloaded Lightroom for my Windows machine and my Mac (technically the same machine, just dual booted). Next, I created a collection on my iOS devices, one collection per device. When you create a new collection on a device, you can tell it to auto-import your camera roll. It will automatically upload your photo's to the Lightroom cloud, and sync them to all of your devices, in the background.

Once each of our devices has a collection created, and has the auto-import enabled, we see all of the collections on all of our devices. This allows us to take a picture on any device, and not have to deal with sending to photostream or AirDropping a large number of files. Our photo's just show up on all our devices. If you want, you could create a single collection, and assign it to auto-import on all devices, so all of your photo's go into 1 collection from all devices. We chose to create one collection per device though so we could make finding a photo easier. I know my wife snapped a photo of my daughter on her iPad, so I just go to her iPad collection from my phone and find it.

Here, you can see all of our collections easily accessible on my iPad.

Now that all of our mobile devices were set up with Lightroom, I launched Lightroom on my Mac and discovered that the collections were available there without any set up. Now I can easily select the photo's and import them in to my library, add keywords, edit them and back them up.

One of the other cool features of Lightroom is that I can select any photo from my library, add them to a collection and enable mobile sync on the collection. Now any photo I add to the custom collection will sync to all of our mobile devices. Extremely easy.


You can technically sync photo's to iOS from Aperture and iPhoto as well, using Photostream. The difference between Photostream and Lightroom Collections is that Photostream still syncs down the photo to your device (albeit a small version), while Lightroom only syncs a thumbnail. Since majority of the time, users won't actually open all 500 photo's to view on their device, you only need 500 thumbnails. As you can see from my photo above, I have 142 photo's from my wife's iPhone, but it's only using 31mb of storage. When you open a photo to view the full photo, Lightroom downloads the full-resolution for you to see. Much better!

With Aperture/iOS, I could share photo's with my wife through Photostream as well, but my wife would end up saving the photo to her camera roll and a duplicate ultimately ended up in my Aperture library. I would spend a lot of time removing duplicates. Luckily, it seems that Lightroom is smart enough to not import duplicates. Another benefit is that I don't have to manually upload 20 photo's that I just took of my daughter to Photostream for her to see. They just show up in our Lightroom.

If I wanted to have a photostream per device, it made things even more complex. Take a picture on my iPhone, and upload to photostream, then take a picture on my iPad 5 minutes later and manually upload to photostream again. With Lightroom, we can take pictures on any device at any time and not deal with uploading. Lightroom handles it all for us with less effort.

Tags & Keywords

Lightroom calls their version of Tags, Keywords. I downloaded an app on my iPad called Photosmith, that lets you create a collection of photos on your Mac (or Windows) and sync the collection of photo's to your iPad. You can then add keywords, edit the photo's, name them and then sync the changes back to Lightroom. It's a great way to 'tag' photo's while on the go. Until the Lightroom Mobile apps support keywording, I'll use Photosmith to do all my keywording while on the go. It's a bit difficult to set up initially, but in the end it works pretty well.

This process is by far the best photo syncing solution I've found, after several years of messing with trying to take care of syncing to the computers wirelessly and sharing across all devices.

Disappointed in Adobe Lightroom for iPad

I can see potentially editing photo's stored within Lightroom on my Mac while I am out and on my iPad. It's unfortunate though that they did not ship the iPhone version with it at the same time.

The work flow that would have me signing up for the creative cloud in an instant is the syncing of my photo's wirelessly from my iPhone to my Mac and iPad. Right now, as far as I can tell, I would have to take the picture on my phone, plug the phone in to the iPad via a camera connection kit and import in order to sync the photo's across my devices.

The fact that Photostream only syncs full-sized images back to the Mac (reduced sizes across iOS devices, so not originals), means that I can't rely on Photostream to carry my photo's from iPhone to iPad and Lightroom.

Until Lightroom ships on the iPhone, so that I can take a picture and sync the original file to my Mac and the thumbnail to my iPad, I can't justify paying for a service that seems half-baked.

I'd be happy if they just provided a temporary work-around by shipping a "Lightroom Sync" app to the iPhone that pulled my phone's Camera Roll photo's and pushed them to my Mac, with no other features.

So I guess I'll just have to continue waiting for a perfect syncing platform.

Managing iOS & OS X photo syncing

One of the most difficult work flows I've had to work out over the last couple of years has been that of photo management. I've had other work flows such as managing tasks that were difficult to implement; mostly because I don't stick to the work flow my self. Photos however has always proved a difficult task to solve.

I've come up with a solid solution that works really well. It allows me to have all of my photos & HD videos from my camera to both my Mac and my iPhone. The big plus is it takes zero storage on my phone.

The problem

You're out with family at a birthday party and take a lot of pictures. You get home and your to tired to pull the photos off, so you postpone it. Before you know it you have 400 photos on your device over several weeks. Then the unthinkable happens - you drop your phone in the sink or loose it at the mall. Photos and videos are now gone. Sure you can retrieve them from iCloud backups, if you have that set up and if you have less than 5gb of photos and videos. What now? You've essentially lost them.

Another scenario is one of you doing a great job maintaining your library. Everything is tagged and filed in a very organized manor. The issue is that your library is 200gb and you can't fit that on your device. I don't know about you, but we take nearly 4gb of photos and videos every month. I can't fit that all on my device.

Solving the problem

Solving the problem requires several things. First, we need to eliminate the need for syncing. The fewer steps needed to back up the photos and provide access from anywhere the better. The second issue that we need to solve for is providing access to all of the content to our devices while we are not at home.

Eliminate Sync

Syncing photos can be completely automated across both Windows and OS X. We do this by setting up Photo Stream on our devices and our computers. Photo Stream will automatically sync your full resolution photos to your computer. No need to plug in a cable. While your device can only hold 1,000 compressed and resolution shrunk photos in your Photo Stream, your computer will hold every single photo until you run out of disk space, at full resolution. So this solves the need to sync your phone in order to get them off your device for the most part. The only thing you will still have to plug the phone into the computer for is pulling off the videos. You can always use Dropbox as an intermediate solution for this however, buy letting Dropbox auto-upload the videos you can then just import them into your library easily.

Next we need to tackle getting the photos made available to your devices even if you don't have room for them. We can do this with a free Flickr account. Flickr offers users 1TB (1,000GB) of storage for photo's and video. You can upload a maximum photo size of 200MB and a maximum video size of 1GB. The maximum video length is limited to 3 minutes at the time being, so keep that in mind while recording videos. It's best to record them in short pieces. Otherwise you will need to split them up in iMovie or something on your iOS device.

The Flickr iOS app has a Auto-Upload feature. Any photo or video you take on your device will be automatically uploaded to a "Auto-Upload" Set (Flickr version of Albums). You can then organize the photo's from your device or from your computer within the web browser however ever you want them to be.

Using Photo Stream and Flickr for wireless syncing of your pictures and videos, provides you with a easy method to get your photo's on your computers without any cables and shared on all devices without taking up storage space.

Organizing on your computer

I used to maintain my photo's within iPhoto, but have since migrated to Aperture. I'm actually looking at moving to Adobe's Lightroom so I can use it cross-platform on my Windows partition and my OS X partition. I have also used Google's Picasa as well and find that regardless of the software you use to manage your photo library, the following organizational system can be applied to them all.

Start by storing all of your photo's in a heirarchial fashion. You place your photo's into a folder (or project in iPhoto/Aperture) based on the event or activity that pertains to that particular set of photo's. Then you group all of those folders under a folder for that specific month. Finally, group all of the month folders into a Year folder. My aperture layout looks like this:

With the above layout, I can easily keep all of my photo's organized in a manor that makes it simple to find pictures in the future.

Next I do some tagging, while this isn't as important, it does help when you want to narrow down a specific search criteria. All of my tags are generally for tagging a specific item within the picture. Such as iPhone, Apple, Toyota or Shopping. I don't tag people because I use the Face's feature to include people. While i am fairly lax on my tagging, I am religious about Face tags. Every photo has a face tag. It takes very little time to do it and provides for an excellent way to search for a specific person or group of people.

Lastly I don't worry to much about tags for location. Each photo has a GPS location, so there is no need to include a tag for it.

Organizing in Flickr

Flickr uses different terminology on their website for their methods of photo organization, but for the most part we can easily mimick what we do on our computers. The only thing that we can't do is nest our photo's as deeply as we can on the computer.

Flickr provides you with Set's, which essentially acts as a photo album. All of your Flickr photo's are stored in your stream and can be added to any number of Sets. If you delete a photo from a set, it still exists in your stream. Sets do nothing more than link to the photo within the stream. Flickr also provides you with Collections. Collections can hold Sets, so I use Collections at the year level, and use Sets at the month level. I dump all of my photo's into their respective month Sets in Flickr and then tag them in the same fashion that I do in Aperture. While Aperture's tags do not apear to transfer into Flickr, some other clients do. I don't remember what i used to manage my photo's in the mid-2000's, but all of the tags that were assigned to them were auto-assigned when I uploaded the pictures to Flickr.

The following screenshot show's how I set up my Flickr.

My Flickr Collections created by Year:

My Flickr Sets created by Month, within a Year Collection:

Since all of the images can be placed (linked really) into multiple Sets, I place all of my video's into the respective Month Set as well as a Video's Set.

Since I can't "Face Tag" people in Flickr, I use Tags here for each individual person.

Putting it into practice

So now when you take a picture on your phone while you are out at dinner you don't have to worry about coming home and performing a sync. Instead, you come home and sit at your computer for about 5 minutes and do some organizing.

Opening up your Aperture/iPhoto/Picasa library, you can go to your Photo Stream folder/section on your PC or Mac and see all of your pictures. Import them into your current Month folder, Face Tag and standard Tag them and then log-off. You're done.

Opening up your Flickr app you should see that the photo's are already inside of the Auto-Upload Set in your Flickr app. You can then select the photo's and link them into your current Month set, add a couple tags and close the app. Your photo's are properly stored and organized on your computer and online in Flickr. You now have full access to every photo and video you ever take, on all devices from anywhere and never have to plug the phone into your computer to do it again.

Lastly, after I import my pictures on the computer from Photo Stream, I delete them from Photo Stream on my computer and from my devices Camera Roll. This ensures that I don't get confused as to what I have already imported in the future and end up with duplicates in my library. Since my photo's are stored on Flickr as well, I don't need to keep them in Photo Stream to view them on my devices. The same thing applies to Flickr. After linking photo's to their Monthly Sets, I remove them from the Auto-Upload Set. I don't think this can be done from the iOS app, so I just do it from Flickr.

This can be done by selecting the You option and then click Organize. You select the Auto Upload Set, drag pictures out of the set down to the bottom and save. Your Auto Upload set has been cleared.

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The entire process, even if you have taken a couple hundred photo's, should only very between 5 minutes and 30 minutes from the time you get home to the time you get off the computer/close the Flickr app.