They’ve already announced “M365 Copilot”, which is in the same ballpark as the Dropbox features (ask questions about your documents, etc.), and of course uses OpenAI like Dropbox does. So the only real difference here would be trust.

I would imagine it doesn’t use OpenAI’s servers, but their hosted versions of OpenAI’s technology though right? Like whatever they’re currently selling to enterprise customers via Azure?

I don’t really know the structure there. Does OpenAI actually have servers? Or do they use Azure servers?

Nope, but it just makes sense as a quick and easy stopgap measure until I find time to figure out who to use, because it's easily compatible with my mac and pc, I already pay for a subscription so it saves money, it can run without putting all the files on every machine that I own, they aren't sending my info everywhere.

If anyone has suggestions on a reliable end-to-end encrypted solution with a lightweight cross platform sync software that doesn't force you to download all the files to your device (my Mac's HD is too small) and is generally fully featured. That won't take very much time to migrate with a trustworthy migration vendor. I'm willing to pay a premium price for it and I'm all ears.

There are several: iCloud, ProtonDrive, Sync.com, etc.

iCloud isn't cross platform enough ProtonDrive is going to pull down every file to every device and act in a dumb way Sync might be a good choice actually. I have to investigate them further

iCloud with Advanced Data Protection turned on is the only one I know of. And it’s obviously Mac only.

iCloud Files is the only major cloud file syncing service that is e2e encrypted afaik. Was my reason to migrate over from OneDrive (especially since I was already using Apple devices and paying for iCloud for photos anyway).

Thanks! I would use iCloud, but I have a few windows devices I need for work unfortunately. It doesn't let me use the advanced security and maintain a windows device. Ironically, like many of these services I already have an Apple One subscription and am paying for it anyways.

Can you trust anyone who claims that things are end-to-end encrypted? Microsoft could take the point of view that you are one "end" and DropBox is the other "end". If they encrypt the data in transit and decrypt it on their end, it's still technically "end-to-end encrypted".

They could also just lie. Having a company claim end-to-end encryption still means that I have to trust that the company isn't being sleazy.

The only encryption you can really have some measure of trust in is the encryption you apply yourself.