Is it going to work on my iPad or iPhone? How long is it going to take? I tried to research that once, but it looked like Dropbox bought whatever service worked well and no longer seemed like a good solution. I would prefer the service to just work out of the box.

Yes, it works on iOS [0]. Personally I’m still using the standalone mode of Boxcryptor (the iOS app is still receiving updates), which unfortunately was bought up by Dropbox, and in the past there were opinions that it worked better than Cryptomator, but many people seem to be happy with Cryptomator now, so I’d give it a shot.

[0] https://apps.apple.com/us/app/cryptomator-2/id1560822163

I found solutions like Boxcryptor cumbersome to use. Unless you stored the data redundantly locally, you had to download big encrypted files in order to access a small file.

Also searching files was impossible unless you downloaded everything, decrypted it, and searched locally.

I quickly realized it was adding huge delays in my day-to-day work and a lot of stress during time-sensitive tasks.

Have these e2ee overlays improved in usability since then?

Obviously you can’t search contents in encrypted state, and with E2EE this means that server-side search is not possible.

I rarely use indexed file contents search (filename search is usually enough and that works well, and tools like grep work transparently), however the Boxcryptor drive can be added to the Windows Search Index (or whatever search software you use), and I assume it’s similar on Mac. You don’t have to decrypt manually. Indexing causes more system load due to the necessary decryption, of course.

On desktop systems I always store all relevant data locally, exactly for the redundancy. I’m not sure what you mean by “big encrypted files”, because each original file is encrypted individually and thus has basically the same size as the original.

Do you want your cloud storage to "just work everywhere" or do you want to have full control of your data? Basically you get to choose one of the two options.

Cryptomater on top of any of the cloud storage providers is a great setup for home / personal use. I have been doing this for the past 3 years with minimal issues. Google Drive + Cryptomater on Windows + Cryptomater on ios, working pretty seamlessly.