As part of my Great Data Reorganizing of 2018, I had followed my colleague and signed up for a personal Adobe Lightroom subscription. If you commit to a year-long subscription, the monthly cost is $9.99, which isn't too bad, although certainly not cheap either.
I had been using what Adobe started calling Lightroom Classic for a few years up until this point, but as I wasn't sure how much longer this app would continue to exist (or be supported), and because I didn't mind basically having an off-site backup backed into the plan, I wanted to give CC a real try. So I signed up, and used the built-in feature to import my Classic library into CC. This took a little bit, but was relatively quick.
Unfortunately, this is where one annoyance popped up already. Most of the photos I make are film photos, digitally scanned for organizing and all that. This means that my photos lack the meta information modern cameras inject, including their shot date, which CC seems to rely on fully instead of (also) looking at the file's creation date. Classic did not have this limitation so in it my photos showed up correctly categorized under their creation year/month, but as this was not correctly imported I ended up with most of my photos made in 2017 and 2018 showing up unordered in a "no date" category. What the heck.
I kind of left it at that for the time being as I ended up busy with other projects and work. Then, around the end of November, I had some time again and wanted to organize my photos. This was in part because I am leaving my job to move back to The Netherlands soon, and up until now I had CC installed on my office Mac. I wanted to transfer my license over to my then newly prepared Hack, which is when I was greeted with a familiar installation error.
I remember running into this issue many years ago, before CC existed even, and even at the time it was obvious Adobe chooses not to support case-sensitive file systems purely because they can't be bothered to write their code cleanly enough.
In fact, back in those days I managed to get Photoshop running after manually copying the application and its files over, and checking the logs every time it failed to boot. It would list a certain file it couldn't find, which it only wasn't able to find because the developers referenced the file without paying attention to its capitalization. So after about 10 minutes or so of doing this, I had a fully working Photoshop.
This was so many years ago, that I had forgotten about it and kind of naturally assumed they had since fixed this, especially with the more modernly built Lightroom. I guess I was wrong.
I contacted Adobe's support, although to be honest I wasn't entirely sure why as I knew they'd probably blame it on someone else at worst, or tell me I had to just re-format my computer and try again at best. They went straight for the worst-case scenario here, and I had technical support tell me this was Apple's fault, and I would have to contact them. Uhm.
I have to admit, I got a little peeved that they actually went out of their way to blame this on another company, so I decided it was time to cancel my subscription. On the bright side, they were pretty quick at getting my account cancelled, so that's good at least.
Now, how to preserve my photos?
Back when I set up my CC account, I had fortunately opted to preserve my original Classic library, so all photos taken and categorized from before the switch were at least still as they were. Still, I thought it would be best to get a full export out before my plan was fully cancelled (note; as it turns out, exporting remains possible even after your plan is cancelled, which is a pretty good move on Adobe's part). I was also curious how potentially useful this export might be, and I of course needed all newer photos I added since making the switch to CC too.
As both my Hack and MacBook are running with a case-sensitive formatted SSD, I had to think on how to get this working. Enter virtual machines.
I had recently set up a macOS Mojave virtual machine on one of my servers and, fortunately for me, had chosen to not go with a case-sensitive format there. I did only use a small ~60GB virtual drive though, but as this is a virtual machine it's pretty easy to modify or add whatever you want. So I made a snapshot of my clean VM, added a large secondary hard drive to it, and went to installing CC.
I think it took about a day to export all ~19,000 photos and videos, which is pretty fast actually. Once it did, I checked out the export folder and was somewhat surprised to find absolutely no folder structure of any kind; it just spat out all images into one big folder. I guess in a way this is not too surprising, but at the same time this might be a strong argument against ever wanting to use CC, as you'll certainly lose whatever folder structure you might've had before.
One of the very important parts you need when considering signing up for a service is how easy or possible it is to get your data/content back out again. While it is very easy to export your images, the lack of file structure might make it more challenging for you as you'll have to re-organize everything again. Of course if your photos have all meta data set by a digital camera (or by you manually injecting them using meta writing apps, I guess), this step might be easier as whatever next tool you import your photos into next will just read this data, but if you want to leave CC to go back to a manually managed folder structure, this can be tricky.
Ultimately, this is not a big warning against using CC. It is actually a pretty good application, for a fair —not great, but fair— price. I am not 100% convinced making it as cloud-based as CC is the right call, but it was certainly cool to be able to pick up any of my devices and see and even edit the photos I took on them, not having to worry about syncing/copying them first.
Just make sure your Mac isn't formatted using the case-sensitive option, or otherwise that you have a secondary computer or virtual machine available to access Lightroom. Although you could of course achieve a similar if not identical result with a Windows VM in this case, for me it was pretty nice to have a macOS virtual machine available after recently setting one up exactly or these types of needs.
With Apple no longer offering Aperture, it really feels like there is a lack of options in this particular market. For the time being I'll go back to a manually organized folder structure, and I keep using Photos.app/iCloud for my iPhone/snapshot-type photos.