Moving to iCloud Photos and What I Learned

One of my earliest digital photos, circa 1994

(And What I Wish I Had Known Beforehand)
I recently made the jump to iCloud Photos. It was a very slow jump, in that I am several days into this jump with many more to come until my photographic feet are on solid ground again. Some of the things that I did in preparing for this jump may have prolonged it. Mistakes were made. Nothing serious, just irritating.

Had I known certain things, the whole process would have been smoother. In my reading beforehand, I didn’t find anything that would have let me know these things, so I’m committing them to my blog, because maybe someone will stumble on them.

Okay, that'll take a while (this is from day four)

Going to iCloud Photos meant syncing photos from three places: two iOS devices and on Mac. My photos are in several other places, as the Photos for MacOS is backed up to my TimeMachine drive. As photos are added to Photos, I also store them on another external drive. I started doing this before Apple released iPhoto, and I’ve never found a reason to stop doing it. My oldest digital photo dates back to 1999, a few years before iPhoto. Over the last twenty years, I’ve accumulated a lot of photos (at ever-increasing resolution), scans of photos, and so forth. What I’m saying here is that my Photos database is pretty big.

Nevertheless, because it was (and will continue to be) the repository for all my photos, I decided that it would be the first set of photos that I would send to iCloud. That was a mistake.

It was also an easy mistake. I upped my iCloud storage to the appropriate amount (lots) and then set Photos preferences to use iCloud Photos. That was the easy part. In retrospect, it probably wasn’t the place to start.

As I said, it’s got everything. Well over 100,00 items. These range in size from a 750 MB video to those early digital photos at less than 50 kB each. This means, of course, that the per-item countdown I’m getting isn’t completely helpful, since uploading that video or one of those tiny pics would knock an item off the list, but they’re not going to take the same amount of time. Progress seems to be newest to oldest, so I’m anticipating that things will speed up as I get to smaller files.

The two iOS devices held a subset, all of which are also on the Mac, with some seventeen thousand items on my iPhone and six thousand on my iPad. Once I had the Mac uploading the massive number of items to iCloud, I set to work on the iOS devices and tried to switch on iCloud Photos. It warned me that my albums synced from iTunes would be deleted. I agreed and I promptly got the message that iCloud Photos couldn’t be turned on.

What follows is a mistake. I looked this up on the web and I didn’t find much. The best answer I had was to sign out of iCloud and sign back in again. That didn’t work. Nor did restarting the machine. I decided that the problem could be the photos already on the iPad, so I methodically exported backups (even though these photos were backed up) and then deleted them. I tried again. It still didn’t work.

Well, if it wasn’t the photos… I cancelled the deletion of slightly more than 6,000 photos and synced the iPad to my computer checking the setting to stop syncing albums from Photos. One of the things that had lead me to iCloud Photos was the inconsistent behavior of albums synced through iTunes, which would typically vanish from my iPad sometime between when I had verified that they were there and when I wanted to show them to someone.

Once the synced albums were off, I started iCloud Photos again. Success! But also something of a mistake. Then I did the same thing to my iPhone. I compounded the mistake. This is a lesser mistake, since getting rid of the synced albums was a good thing. My sequence was off.

At this point, things were slowly beginning to make sense. I was beginning to see see the error of my ways. The iPad took a couple of days to finish uploading, after which it began downloading (which it’s still at). There are still black bars where I deleted photos which are now being re-dowloaded. Because I sent things to be deleted, I’ve been making a daily round of the Recently Deleted album to make sure that none of my photos end up there.

It also became clear that every device was uploading things in reverse chronological order (either by file date or import date). Time creeps backwards. For the Mac, it was clear that anything new would wait until the end, while the iOS devices and iCloud did share their new content. There’s probably no way around that, but the process might have gone smoother if I hadn’t had three devices uploading at the same time (as I write this, I’m anticipating another two days for the iPhone, after which the Mac is on its own for uploads, apart from now photos).

This Is How I Would Do It
If Apple’s TimeMachine really could turn back time and I could take my current knowledge back to when I began, I would do this (so maybe you, gentle reader, can profit from my adventures):

An important step: The first clean-up step would be to remove the albums synced with iTunes. Since if everything goes right, they vanish anyway, it’s no loss to speed them on their way.

Then I would sync the device with the least number of photos and videos first. (In my case, that would be my iPad.) Move from there to the next item, only as a final step send the remainder of your photo library to iCloud.

Had I done that, at this point, I’d have all the same photos on my iPad (less the albums shared from iTunes, though they’d get there eventually) and it would be adding photos from my iPhone (which is most certainly is doing).

This is all working. I’m going to get there (and I’ll probably make another blog post about it). With just a bit more knowledge, I probably could have got there more quickly and easily. I think I’m going to like iCloud Photos, but there will be a delay getting there and that delay is partly my fault.

Wish me luck.