Best practice for migrating to iCloud Photos?

I’m looking for advice on how best to migrate to iCloud Photos for a user with MacBook + iPad + iPhone. Objective is one single library of photos in iCloud that all three devices can view, curate, edit, etc.

Background: I’ve been using Apple’s photos applications on my MacBook Pro for years – first iPhoto, then the present-day Photos program. I tried enabling iCloud Photos when it first came out years ago. At the time, I probably had 5K images in the library on my MacBook. Things went terribly wrong - operator error, no doubt, combined with bugs in the new functionality required for iCloud syncing. My library got hopelessly corrupted. Had to delete everything, turn off iCloud Photos, and restore the library from Time Machine. Wasted days/weeks, and swore off iCloud Photos forever.

But perhaps it’s time to embrace the future. So I’m looking for advice on how best to proceed, and avoid the morass I encountered last time.

I assume the First Step would be to enable iCloud Photos on the Mac. Leave it be for a day/week (without sleeping) so the initial upload to iCloud can proceed. I have the 50GB iCloud+ storage plan which should be ample. If not, I’ll upsize.

Step Two: enable iCloud Photos on the iPhone?? The iPhone has lots and lots of photos and movies on it, some of which have already been moved to the Mac’s photo library - some via ‘direct transfer’ (usually Air Drop), some via My Photo Stream. As a result, there will be a lot of duplicates.

At some point, I assume that having enabled iCloud Photos on the iPhone, images will start downloading from the newly-created library in the cloud to the iPhone, bringing it up to date. Not full-size images, but thumbnails. Since the iPhone has limited storage, I should enable Optimize iPhone Storage. It’s not at all clear how Apple deals with the bi-directional syncing that’s required, but I assume that’s all taken care of:-)

Step Three: after the iPhone reaches steady-state, enable iCloud Photos on the iPad and let it sync to the iCloud library. As with the iPhone, I should enable Optimize iPad Storage.

Re the duplicates: After the three-way syncing completes, I thought I’d be able to deal with them within the Photos app on the Mac, but I’ve learned that the auto-generated Duplicates folder seems to be a feature added to Ventura. My Mac has Monterey (with no current plans to upgrade to Ventura), so perhaps I’ll have to winnow out the dupes on the iPad (which has iOS 16). That’s less than ideal, but may be viable.

If I decide to proceed down this path, I’ll ensure that the Mac is configured to keep local copies, so the complete photo library will get backed up. (I run both Time Machine and Backblaze, and also make a clone of the Mac’s SSD with SuperDuper from time to time).

Thanks for any advice on how best to achieve Photos nirvana in the cloud. As well, warnings about any pitfalls that may be lurking will be gratefully received.

Hi David,

I’ve done this process with clients many times… and I would enable iCloud Photo Library on all 3 devices at the same time and let them upload and merge over a few days. Avoid cleaning up, organizing, dealing with duplicates… all of that stuff until after you can see (at the bottom of each devices Library view) that they have all synced.

Yes, optimizing storage is a must on those devices that can’t fit the entire library. Yes it’s fine to download all originals to your Mac if it has room.

Backups here are the same: Time Machine, Backblaze and Clone. My entire photo library is on my mac. The iPhone and iPad are optimized. Shared Albums are on on all devices.




Hi David,
My Question- I have a similar desire to consolidate all my photos, as David C…

Unfortunately, over the years, many of my photos are ‘filed’ in separate folders on my Mac, (not in Photos). They got there by me transferring them from my iPhone to the various folders using Image Capture.

Added Complexity issue: Some of the folders contain photos taken with my old Canon compact cameras, so those pics do not contain all the metadata that modern iPhone photos do… creation date, etc. Some are not even in the file format that present iPhones create. Will all these ‘legacy’ photos be somehow bunched at some place in the iCloud system not properly organized? Will iCloud, Photos even ‘accept’ them?

How do I ‘re-introduce’ all these various photos to the Photos App, with their metadata, then have them ALL stored in iCloud, etc. (as David C. Wants to do).

Thanks in advance for any help.

Like you, I have lots of folders of photos, scattered around my HD. Some came via Image Capture, some sent to me over email, some downloaded from the interweb, etc.

It’s easy to get these added to the Photos library on your Mac - just drag a folder containing such photos on top of the Photos icon in the Dock (or into the the Photos window itself if the app is already open). The enclosed photos will be imported into the Photos library.

You indicated that some of the legacy image files may not contain metadata about each image. If you want to introduce a modicum of organization structure to the newly imported photos, you can get Photos to add data/time. Imported items will be listed under Imports (under ‘Photos’ in the left-side pane). Select a bunch of them, perhaps the contents of an imported folder. Then under the Image menu, select Adjust Date and Time. You can add a suitable date/timestamp to all of the selected photos in a batch. You don’t need to be precise - perhaps “June 1, 2015” for the assortment of vacation snaps from summer of 2015. “Dec 1,2010” for holiday snaps from that year. Etc. The benefit of doing this is that the imported photos will then appear in the library timeline in approximately the right order.

It might also be helpful to add keywords to imported photos so you can locate them later. Perhaps “Canon” for pictures taken on your old Canon, or “Nikon”, or “Pentax”. I tag all the photos taken with my GoPro accordingly. Use the same technique to apply keywords in bulk: select a group of photos, then cmd-I to open the Info window, then enter the desired keyword in the Add a Keyword field.

If you set up a bit of a structure to tag the legacy photos (or any of your photos), it’s easy to then create a “smart folder” to auto-select them. Example: I have a smart folder that contains all my GoPro images.

You asked if Photos will ‘accept’ images in legacy file format. I assume you are referring to JPEG format, which has been the de facto standard used by digital cameras for decades. Modern Apple devices now use a newer format known as HEIC. The Photos app will happily import JPEG images (as well as the newer HEIC).

You asked if the ‘legacy’ photos will be somehow bunched together in the iCloud system. AFAIK, the answer to that is no. iCloud Photos doesn’t impose any organizational structure to the images that get synced from the Mac to the cloud. It just hoovers up everything that gets uploaded from your Mac (or iPhone, or iPad) and maintains a synchronized library in your iCloud storage. It’s up to you to organize items in the Photos app as desired. Hence my suggestion to tag your old photos with “Canon” or other suitable keywords.

Jason Snell’s Take Control of Photos e-book is highly recommended to tackle the complexity of managing photos across Macs, iPhones, iPads and iCloud. I’ve found it quite useful.

Hope this helps.

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Some remedial steps I recommend to all my clients who want to consolidate photo libraries and start using iCloud Photos:

  1. Run Disk First Aid on the volume(s) by booting into Recovery Console
  2. ALWAYS update the OS to as recent a version as your hardware will allow
  3. Do this on a FAST network (problems always seem to crop up with timeouts, etc. on <100 Mbps)
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Thanks for the tips. It wasn’t obvious to me that iCloud will deal happily with 3 devices syncing at the same time, but I will take your advice.

You’re welcome!

I was dealing today with photos spread across many drives and many decades… I imported them in 5 to 10GB batches and all went great. jpeg and raw files, movie files, no problems. Do note that PDF files will get ignored, so you need to keep those elsewhere.
Tomorrow’s task is to import an old 600+GB Photos library. That should be fun! But it’s built in now in Ventura, import → old library. We shall see how it goes!

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