Using iCloud.com to upload your photos – or why you really shouldn’t even try

I recently found myself in a situation where I had to use iCloud.com to upload photos (and video, but more on that later). I had to use the website, because it wasn’t my data and the person only had a very old Windows PC and no Mac. I figured the iCloud website would be a perfectly viable way to get those files (only around 10 GB in total) into the cloud to be accessible on an iPhone and iPad.

I started my process on the PC (yes, it’s running Windows Vista 🤷‍♂️), trying to use the iCloud application that supposedly allows for automatic upload from a pre-defined if you so choose. That didn’t work once, even for the smallest of JPGs, which may or not be because of the age of said PC and numerous other possible reasons. Also: Debugging something like this on a Windows machine that takes 30+ seconds to open an Explorer window isn’t very high on my „Favorite Things To Do”-list.

After that path was a dead end and I couldn’t (read: didn’t want to) diagnose why, I tried using Chrome and Internet Explorer which gave me repeated errors while trying to upload more than a few files at once. After all it might also be related to Windows, Chrome or IE or any mix of these.

I even tried to copy the files to an SD card and use the Lightning to SD card adapter to re-import photos to the iPhone and iCloud Photos. Just copying files on to the card wasn’t – as I expected – enough. I probably had to create the whole folder structure to make it appear like the files just came from a camera. But that way I wouldn’t get albums or at least make it very hard to recreate them.

So I went to copy the files to a thumb drive, which took ~30 minutes for 10 GB to an otherwise very fast USB stick. After that I copied them to an older 2013 MacBook Pro, only to find out iCloud.com really is a really horrible way to get anything done. The same errors persisted, although not as permanent – sometimes I could get 20 or 30 photos to upload at a time before it would error out. Other times it would just silently fail and while the browser pretended it was still chugging along. It’s not a matter of upload speed, I can get a solid upload of 20+ Mbit/s out of this line.

Also note that the website states that you can add photos and videos. However if you try to upload anything else than a JPG file, it will give you an error. Videos taken with an iOS device fail as well as screenshots created on an iPhone or iPad. I’m not yet sure how I’ll get those files into Photos on the iPhone, I might upload them to iCloud Drive and see if I can add them from there to Photos on the device itself.

My very last resort would be adding a new user to my Mac and use Photos to eventually get everything uploaded. This would mean however adding someone else’s account to my Mac which I’m not sure I – or the other person – feel comfortable with.

This whole process goes to show that moving from a world of Macs or PCs to just iOS devices is still a giant pain. iCloud.com is just horrible. If this was a website managed by Google or Dropbox, I expect completely different results. It would just work. Uploading files to the internet doesn’t require some black magic. It’s just feels painful if a company like Apple isn’t capable to make it work.

Apple could give its Files.app the ability to read thumb drives or – heck – SD cards that didn’t come straight from a camera. Instead, you have to jump through hoops in this brave new „Post-PC world”.