Thursday, November 17th, 2022

How I moved to Apple iCloud – and the lessons I learned on the way

Graphic showing various data sources being uploaded to Apple iCloud

After a couple of years on Microsoft and Google, it’s time to return to Apple iCloud. Amongst the many things I needed to do was set up my cloud storage, and in particular my personal photo library.

In this post I’m going to walk through how I did it and some of the issues along the way.

Getting everything ready.

Before I started moving files around I had some housekeeping to take care of. This made uploading my files easier and meant I wasn’t moving things around I didn’t need.

  • I went through OneDrive and tidied up my filing. A few folders had spawned for projects that went nowhere, each full of duplicate files to be deleted. There were also past projects which I compressed into .zip files. Once all this was done, I backed everything up to my external drive. 
  • My photo library was in Google Photos, which I back up every month to my external drive. I saved the latest images as this is my source for Apple Photos.
  • I made sure my Mac had as much free space as possible. I cleared out a couple of TV shows that had found their way onto local storage, removed my music to the external drive and deleted trash and downloads. Any OneDrive files held locally were also removed using Right Click – Free Up Space.
  • Finally, I set up my Mac. Because it can take a while to download and upload files, I stopped my MacBook Pro from sleeping. In MacOS Ventura this is under the Advanced options in Displays in the settings app. Older versions of MacOS might find it under Battery in the settings app.

Now all this was done you’d think it would be easy to just drag and drop stuff from OneDrive into iCloud.

Hold that thought.

Moving files to Apple iCloud

Both OneDrive and iCloud are integrated into the MacOS Finder. Copying files from one to the other is as simple as drag and drop. Amost.

  • First, drag-and-drop moves files from one place to another. This means they’re removed from OneDrive and put onto iCloud. If, like me, you want to keep a copy “just in case”, remember to hold down the ALT key.
  • Second, it works by downloading the files from OneDrive, putting them onto a local copy of iCloud, and then uploading the files. This is quite demanding on bandwidth and can take a lot of time, depending on how fast your broadband is.
  • Finally, I found OneDrive got confused from time to time and started throwing up errors about missing files or losing access to “helper applications”. For folders with large files or lots of them, I found saving the files locally solved the problem. You do this by right clicking and selecting “Always keep on this device“. Once the files have been copied to iCloud, right click again and select “Free up space“.

In all I shuffled about 300GB of data from OneDrive to iCloud. It took a few hours, although I am using high speed fibre broadband. Most of the time it ran in the background while I got on with other things. Apart from the fan kicking in I didn’t notice any slowdown in editing files in Affinity Photo, or tapping away on Pages.

Apple Photos: a bit of a nightmare.

My main reason for moving to iCloud is Apple Photos. I prefer it to Google Photos, and now I’m using my iPad Pro a lot more, it’s also easier to use.

Again, the theory is I can drag and drop photos from my image archive into Apple Photos and they get whisked up to iCloud. However, this was the task that caused the most problems.

First it is incredibly slow. To upload a 300GB, 35,000 image library has taken 5 days on high speed fibre broadband. This is orders of magnitude slower than moving files to iCloud. My theory is Photos does a lot of background processing to the images, primarily to set up indexes for facial recognition, locations and image searches.

I’ve seen numerous reports it can take weeks, if not months, to upload large image libraries from iOS/iPadOS devices. This is usually from people who have left their photos on their phones, or used Google Photos instead of Apple Photos. If you can, I suggest using a MacOS device and the fastest broadband available.

Second, I kept running into “insufficient memory” issues. This appeared to be caused both by Photos needing a large chunk of disk space for a cache, and the slow upload speed.

Before I started, I set Photos to “Optimise Storage”, which means the full sized images are saved in iCloud, and smaller versions are kept locally. Even with this set it took 3 separate uploads across 5 days to get all my images into Photos.

Google Photos: problems with the archive.

With my Google photo archive successfully uploaded I thought I was close to being finished. However, a casual glance through the import revealed a problem. Large numbers of images across a wide time frame were missing.

A little digging exposed a quirk in the way Google stores physical image files. I’m not sure why, but images can be duplicated across multiple folders. While you might think a folder called “Photos 2016” might have all of that year’s images in, it doesn’t. They can be found across many different folders corresponding to the album you added them to. If you’ve added an image to 3 or 4 albums you could find them duplicated 3 or 4 times.

I solved this problem by downloading a new “Takeout” from Google and importing the image files.

  • I downloaded each 50Gb archive file in turn
  • Expanded it on my MacBook
  • Searched for files of type “jpeg” in the takeout folder so I had all images in one list to work with
  • (Don’t search just for “jpeg” as it’ll return a load of json files as well. Also, limit your search to the Takeout folder only, otherwise you’ll get everything on your device)
  • Ordered images by name and dragged them in batches of 1,000 into Photos
  • When prompted about duplicates, checked “apply to all” and “don’t import duplicates”
  • Repeated until all images had been processed.

Every 4 or 5 drag-and-drop sessions, Apple Photos reported a problem importing files, and threw up a list of files it had failed to import and the reason why. This was caused by two issues:

  • first, some of the images had been corrupted by Google and lost their metadata. I couldn’t recover these files, so deleted them and moved on. Fortunately most appeared to be duplicates based on their filenames and folder locations.
  • second, Apple Photos cache seems to run out of space every now and then and needs to be reset. A simple restart of the app and drag/drop the batch that caused the problem cleared it.

How Apple Photos clears duplicate photos.

Having imported several tens of thousands more images, duplicates were inevitable. This is where Apple Photos came into its own in building a newly merged system of record. The app processes files on the device, looking for duplicated files and reporting them in a folder called “Duplicates“.

Overnight I left my MacBook locked, but not asleep, and let it do its magic. Come morning, it had found the 12,000ish duplicated images. Rather than go through each duplicate in turn, I decided to trust the tech, selected everything and clicked “merge”.

On most images this worked well and dropped the merged images into their correct place in albums and the photostream. However, a few got left behind as it couldn’t resolve the date the photo was taken from metadata and defaulted to the date of the image file. As this date was when the Google Takeout was created it placed all these unresolved images in one place in the photostream. I added them all to a “to edit” album and worked through the list. It took about an hour as most of them were either images I no longer needed (old screenshots or images I’d shared), or came from a holiday in Brussels.

I’ve no doubt there are still duplicates left, particularly as Google Takeout saves both edited and unedited versions of a file, even if all you’ve done is rotate it. I’ll clear these over the coming years as I look back on my albums.

The iPad dimension.

While Photos was busy uploading files from my MacBook, it turned out my iPad Pro was hard at work too. When it’s asleep and connected to power it processes Apple Photo images, and it was here that my first “People” albums appeared.

I could also organise the images that had been uploaded. I created the bare bones of my album structure and started sifting through images to find things to share.

Fortunately I was able to add new images from both my camera and Android phone while the MacBook was hard at work. The former I added using the Wi-Fi connection built into the camera, then importing jpegs into Photos. The latter I imported by using “Save to Device” in Google Photos.

However, none of these changes or new images arrived on my MacBook until after the MacBook was finished.

My suggestion is if you do have an iPad, leave it connected to power and asleep overnight. It might make some of the processing go more quickly.

A mistake: optimizing Mac storage.

One mistake I did make was optimising the space iCloud takes up on my MacBook. While I was looking at settings and trying to unravel how Photos was storing images, I accidentally deselected “Optimize Mac Storage” in the iCloud settings. Realising my mistake, I immediately reselected it.

Unfortunately, iCloud had taken that first deselection as an instruction to download everything onto my local storage. As far as I can see there’s no way of cancelling it. Eventually it failed as there isn’t enough storage space for everything. This was after a very long wait for files to download.


Apple is clear that iCloud is NOT a backup option. While having your files stored away from your machine might give you some comfort, it isn’t robust enough to serve as a full backup of all your precious images, videos and files.

That said, I do use it as an online backup in case something happens to my external drives. My archives are zipped and stored in clearly labelled folders away from where I do my day-to-day work.

If you do a backup after syncing your photo library, remember your device may have smaller files saved, not the originals. To get the original files, select them in Photos, then choose “Export unmodified originals” from the File menu.

Final thoughts on migrating to iCloud.

If you are going to make the switch, a few things to bear in mind:

  • organise and backup your files on your old cloud drive BEFORE you move them across. It’ll speed things up and means you have a backup ready in case things go wrong
  • remember to COPY files from your own cloud to iCloud by holding down the ALT key when you drag and drop
  • disable automatic sleep on your MacBook while you migrate, and leave it plugging in and switched on. You can still lock the screen
  • Photos takes a long time to upload files, although you can still work on your Mac without losing much performance. Be ready for a long wait to see all your photos
  • Double check everything and if need be, import from other archives. Apple Photos does a reasonable job of finding and resolving duplicates
  • Don’t switch off “Optimize Mac Storage”, even by accident, as iCloud will try to save everything to local storage on your device.

Overall I think iCloud is a decent cloud service. The initial upload is slow, particularly with Photos, and it can be slow if you’re trying to move large files (or lots of them) around. That said, it is easier to use on iPadOS and MacOS than OneDrive and Google One, particularly with photo libraries.

My name is Ross Hori

I'm a freelance writer, designer and photographer. By day I create articles, features and reports. At night I take photos and write fiction. Find out more.