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However, this solution isn’t ideal for people who don’t want ANY plaintext versions of their files on their hard drive.

There are two solutions for you and Svante touched upon one if I understood him correctly.

  • Folder mirroring. Let’s say you have several confidential folders on your hard drive – Tax Returns, Bank Statements, Client Files and so on. You then tell AxCrypt that these are Secured Folders. This’ll cause AxCrypt to encrypt them automatically. You then have your cloud upload everything with a .AXX extension (if your cloud provider allows such functionality). The alternative is to duplicate those folders – like Tax Returns but add a word like Secured after it: Tax Returns (Secured) and create a little script on your PC to only copy .AXX files. The final idea would be to use Windows File History to only backup .AXX files to a particular volume. You then sync your cloud folders to that encrypted volume. You could even have a virtual hard drive in windows like the J: drive for example.
  • Encrypted cloud. I know several people on here have recommended them and they’re the easiest of solutions when you can’t trust your existing cloud. They work on all sorts of devices (PCs, Macs, Androids, Windows Phones, Blackberry, iPhones, iPads, Linux) but they’re paid-for solutions. With an encrypted cloud the cloud provider doesn’t keep the keys and they encrypt everything locally (it’s done transparently). If you forget your password then you’re f****d, you can only delete your account and start again. It’s not like Google Drive where you can Reset Password. They’re also expensive. The cheapest individual plan is 8.33€ per month going up to 20€ per month. The two main ones are Tresorit (has the most apps, easiest to use) and Spideroak One (fewest apps, more for glaciated backups).

I have colleagues who use encrypted clouds and then use software like AxCrypt to encrypt the extra-sensitive material. It’s unnecessary to twice encrypt things in my opinion, and bordering on the paranoid, but I don’t know what sort of material you’re encrypting and I don’t want to know either: that’s your private business.

I use AxCrypt for the occasional file and if I want to share a confidential file with a friend I use my cloud to create an encrypted link which only the friend can access. The recurring cost of such clouds might be prohibitive for you and they’re nowhere near as cheap as AxCrypt which only costs 3€ per month compared to 8.33€. You might also be tied into an existing cloud which makes migration hard.