Wireless, cross-device, photo syncing in 2017

I've been meaning for a long time now, to share what I'm doing in regards to synchronizing photos across all of my devices. I originally posted back in 2014 how I was doing it, and again in 2015 with updates as technology changed. In 2016, my photo synchronization strategy changed once again, but I never got around to writing a post on it. So here I am, in 2017, sharing what's changed. As is usually the case with these posts - it's hefty. So get yourself your favorite beverage and snack!

What's changed?

Before we get into the nitty-gritty details, lets take a look at what i've changed first.

From a sync perspective, I've stopped using iCloud. It was a huge pain to deal with when trying to manage my photos in Lightroom. Exporting them from iCloud Photo Library, into Lightroom, tweaking them etc, and then re-importing the photos back into iCloud was extremely tedious and time consuming. Because of this, I found that I hardly ever actually migrated photos and it made it really hard to go back and find photos over time. Remember, this was early to mid 2016 - so iOS and macOS Photo apps were not as smart as they currently are now.

Ultimately, I setup a Google Photos library on my Google account. I then synced my entire Lightroom library into Google Photos. This worked amazingly well. The iOS Google Photos app would automatically upload my new photos in the background, and they'd sync down to my computers into my Lightroom library folder - ready for me to just perform "add missing files" in Lightroom. Any changes I made to the photos were immediately synced to all devices, because the library and photo lived in the synchronized Google Photos folder. The setup for this is explained in detail further below.

The biggest thing however is that I've stopped using Lightroom for photo organization. That does not however mean that my current solution wouldn't work with Lightroom. I was using Lightroom when I changed my syncing solution, and it worked without a problem. I just found that Google did such an amazing job with searching images, that I no longer needed to spend so much time organizing them myself. I now let Google Photos handle all of my organization needs. I explain this in more detail below.

The biggest gain from this change, for me, is that now my photos are synced across all devices, even those that are not Apple. We have an Android device in the house, and a couple Windows machines. All of which have my photos synced to. My wife has the Google Photos app installed on her iPhone and iPad, connected to my account. So her photos now sync into my Google Photos library (and at one point my Lightroom library). With virtually no management on my end, I'm syncing photos from 2 completely different Apple accounts, into a single consolidated family photo library. That's a big win for me.

Moving to Google Photos

When moving to Google Photos, there are a couple different routes you can take. It depends on what your end goals are.

The free solution

If you are not currently using any app, like Aperture or Lightroom, to manage your photos then setting up Google Photos is easy. You just install the Google Photos iOS or Android app, and configure it to automatically back up your photos. On iOS, it looks like this:

When you turn on Back up & sync, Google Photos on iOS will automatically back up your photos for you to the Google Photos service. Google Photos gives you unlimited photo uploads for pictures that are 16 megapixels or less. All of the current iPhones on the market take photos at less than 16 megapixels, so you can use the service for free with no limits. Google Photos will also let you store unlimited 1080p videos as well. Since some iPhones on the market can record 4K video, you would want to choose whether or not you want to record in 1080p so you can sync them for free, or record them in 4K and upload until you run out of storage space, which is 15gb on the free account.

If you go this route, all you have to do is install and sign in to your Google Photos account on all of your phones and tablets. Then you can access the photos from the Google Photos website on your computer.

The integrated Desktop solution

If you are using an app to organize your photos, or are wanting to start using one, then you'll want to get this photos synchronized to your desktop computer. This is extremely easy to do, at the cost of paying a monthly subscription to Google Drive. I currently pay $10 per month, for 1 terabyte of storage. Once you've done that, you can go to your Google Photos settings, from the website, and turn on Google Drive.

Once you have turned on Google Drive support in your Photos settings, you can install the Google Drive app on your macOS or Windows computer. Once it is installed, it will automatically sync all of your photos from Google Photos to your computer. Here you can see that my original Lightroom based organization is still intact, even though these photos exist now in Google Photos.

Since I stopped managing photos myself, any new photo I add to Google Photos gets put under the Google Photos folder, within a folder indicating the year the photo was created. This is why you see Google Photos\2010, and Google Photos\Digital Photos\10s\2010. Google will at least organize your photos by year for you automatically, if you choose not to use any software to manually handle this.

With this, you now have every photo you take, regardless if it's an iOS or Android device, synchronized to your desktop computer. From there, you can open Lightroom, select the Google Photos directory and have it import all new Photos for you. Once they're imported, any changes made to the photos, (including their file location as long as it's someplace under the Google Photos folder) will be synced to all of your devices automatically.

Leaving Lightroom

So now that we've talked about my synchronization solution, let me spend a couple minutes explaining why I moved away from Lightroom all together for my organizational needs.

The biggest reason is time. I don't have much of it, and I have to set aside a block of time to organize several hundred, or a thousand, photos every couple of weeks. My organization routine typically included moving the photos into sub-folders representing the activity that took place, tagging every photo and confirming facial recognition. This usually took a minimum of two hours for me.

Enter Google Photos. They do most of this for me. The only exception is that they organize the photos under a single folder, representing the year. Where-as I would break the photos up under a year, by month. Here you can see Google Photos organization of the photos since I stopped doing it myself, for 2017.

They organize them in a single directory for the entire year. When I used to organize them in Lightroom, I organized them by year, month and activity as seen here.

I now just use Windows Explorer to move specific sets of Photos into sub-folders if I need to. Any photo that is stored within a sub-folder of the year, will let Google Photos create an album for it. For instance, in my example photo above, I have a folder called eating at Islands Burgers. Google turned that into an album for me, so when I search for Islands Burgers in Google Photos (regardless if it's the mobile app or website) their auto-complete will know what you mean and present it as an option.

This to me is pretty awesome. My custom organization strategies can be persisted across all of my devices using Google Photos this way. So why pay for Lightroom for organizing? Just organize them in Windows Explorer if you want. If I were to select the Eating at Islands Burgers album suggested to me, I would be presented with the album (represented as a folder on my computer) as shown below.

Now, Lightroom does some other things - such as tagging your photos. Unfortunately Google Photos doesn't read your tags or support custom tagging of photos. Here's the crazy thing though. They scan the photos for content and automatically associate tags for you. From my experience with it, it does a far better job of it than I ever did. For example, I can search for all photos of Batman - and get back comic books and clothes. None of these photos were tagged by me in Lightroom. Even the blanket in the photo has batman in it!

Another example is searching for "Zoo", which presented me with photos both my wife and I had taken at the various zoos we've been two. It also included two different albums we had created with photos from different occasions.

I've searched for Nintendo controllers, Monitors, 2006 Scion Xb, Chihuahua and have been given every photo containing these items. It is amazing when you experience it for the first time. Once I used it enough to see how accurate and thorough Google Photos tags stuff, I stopped worrying about tagging things myself.

Lightroom supports facial recognition, and so does Google Photos. Google Photos does an amazing job of it though. I synced photos of our newborn daughter and assigned her a face in Google Photos. From that point forward, as we take pictures of her it automatically assigns her face to the photos. Even though she's now 3 years old and looks completely different from the 1 hour old baby I first uploaded a picture of, Google Photos has kept up and figured it out. Since Google Photos handles this, I stopped using this feature in Lightroom.

The last thing that Lightroom is good at is editing the actual photos. Google Photos has some basic tools, like crop, rotate etc. It even has a few filters you can apply. It's not the powerhouse that Lightroom is though, so if you find yourself editing photos often, you'll still want to keep doing that in Lightroom. This is something I hardly ever did, so it was just one less reason for me to keep paying for Lightroom.

Even though Google Photos can automatically do a lot of what you have to do manually in Lightroom, there isn't anything stopping you from continuing to use Lightroom.

Google Photos Assistant

Google Photos has a feature called the Assistant which will automatically take photos you've uploaded and turn them into albums, collages, home movies and animated gifs. It's really awesome. For example, it took a series of photos over the course of two weeks of my son and organized them into an album and collage for me called Highlights of Oliver

Selecting the Highlights of Oliver tile opened up the collage so that I can vew around 20 photos of him over a span of two weeks. Photos taken by both myself and my wife, which is really a nice touch.

Google Assistant on Android

The last thing that's neat, if you are on an Android device that supports the Google Assistant, is that the Google Assistant will search your photos too. Here I asked the Assistant to find photos from a park, and it knew not to just do a Google search of park pictures. Instead, it searched my personal photo collection and find some photos. If I touched the Google Photos button, it would open the app and give me a wider selection of images to look through.

Wrapping up

I've used this system for over a year now and love it. It has simplified the way I do photo synchronization and management across all of my devices, and my wifes devices.

Migrating from Gmail to Outlook.com


I have used Gmail for years, it has always been the best of the major email services out there. It had the best search, a great filter system and it was fast. 

Times have changed though. It's search doesn't work like I expect it to. I've searched for several product licenses that I know exist in my Gmail, but can't find them. I know they exist; I migrated my email over to Outlook today and found them instantly. It's forced me to use apps like Evernote and 1Password to save that information. 

Gmail's filtering is to complicated. I know it's powerful, but I find myself searching google for how to perform a specific filter because I can't figure it out. I tend to get frustrated and move on without finding what I was hunting for. 

Google uses a label system that's very confusing. I can apply a label called "Work to an email and then move it into the same "Work" label like it's a folder. I understand that they do it for flexibility in filing; make it easier to store the same email in more than one location in your inbox, but it's really annoying and frustrating when you have thousands of email messages and you still can't find what you're looking for. I know some people will think I don't know how to file properly, and maybe that's true. If it is, come and show me how to properly organize 10,000+ emails with labels and then dig through the emails associated with a label or two to find the content you need. It's not easy. 

I also don't like the whole `archiving` and `all mail` thing. When I delete a message, I want it deleted. If you want to _"archive"_ it then fine, but don't include it in the stupid `all mail` folder. I deleted it so I don't see it again. I apply labels to things I want archived. Archiving every single piece of email that I receive is just stupid. 

Lastly, Google had Google Apps Standard; a free service for those that wanted to use a custom domain and have access to some of their Google Apps items. In December of 2012 they removed it. Just like a lot of other great things they've removed. I want a personal domain associated with my gmail without having to provide people my gmail account and I don't want to deal with mail forwarding. To be honest I was a big angry that they got rid of that feature unless you are a business and pay for it. I have no problem paying the $5 a month for the Business Google Apps except that I already pay it for my business and and don't want to setup an account using a _"fake"_ business just to use it personally. 

On top of that, their UI and service features hasn't changed much, with the exception of how they scan my emails and deliver targeted ads. That's improved. 

So I gave up. It's time to pack up all of my email and move on. 


Let's be honest, Hotmail and Live sucked. Really bad. It was full of spam and my hotmail account was hacked like 4 times. However, just like Google, things have changed with time. For Outlook it seems to be for the better. 

The first thing I did was use a feature that I was not aware that Microsoft offered. The ability to use your own custom domain with a Outlook.com email address. This worked really nice! Not only was the process extremely easy to set up, Microsoft provides my custom domain with 50 free email addresses that I can use. This really helps me out, as now I can have my personal email address as something related to sullinger.us and I can have a support email address at support@sullinger.us. The nice part here is that I get the same thing that Google Apps Standard was offering when it was free, prior to them going business only.

The next thing I did was import all if my Gmail email into it.  The import process took a lot of time. By the time of this writing, it had been importing for roughly 6 hours. Luckily, this is a server side process; I don't have to sit and not close my browser. I closed my browser and let it import. I have a ton of Gmail emails, so this is to be expected.

The sweep feature of Outlook.com is really nice and I can see it really improving my ability to get to inbox zero. I can select an email and tell Outlook.com to move all emails from this sender to a specific folder, delete all emails from this sender, schedule a clean up or create a rule from this email. Using the sweep feature, I was able to re-organize about 1,500 email messages imported from Google (it's still importing) in under an hour. It's really impressive how productive one can be with a tool like this.

The last thing that I really like about Outlook.com is that it uses the Exchange ActiveSync server for clients to connect with. This means that I actually get real push on my iOS devices. Something I do not get with Google. Instead, I have to pull new mail down the from server every so many minutes (chosen) or manually. It's annoying.


Migrating from email services can be a real pain. I'm currently focusing on just migrating from Gmail for the time being. However, once the import process is completed, the emails are organized and I have refreshed the sites I visit that use my Gmail email, I will probably start the import process on iCloud. I like iCloud as a service, but it lacks way to much functionality to be a good email service. 

I really like having my contacts in iCloud, along with my calendars and tasks. Unfortunately, Microsoft and Apple haven't worked together to get iCloud to work on OS X's version of Office 2011. So I have to decide if I want to move my contacts and calendars to Outlook.com as well or just leave them in iCloud. Moving my email to Outlook has made it a pain to email contacts, as I can't get my contacts from the OS X Contacts app over to Outlook 2011, up to Outlook.com. I don't want to sync my tasks with Outlook.com because then I would loose the ability to use Siri. So it's not a perfect solution just yet. Odds are I will migrate my contacts and calendars to Outlook.com, but I haven't 100% decided yet.

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