How to setup disk encryption + periodic backup (SSD -> HDD -> Cloud) on a dual-boot environment?

Solution 1:

Just some general statements to a very broad question.

There are many encryption schemes, some OS-dependent, some relying on hardware, such as TPM, some performed by software such as VeraCrypt. You might research encryption standards, and decide what level of security is needed and what competencies are required for its implementation.

That said, some notes on "backup", i.e., disk imaging in the case of an encrypted drive.

  1. If you encrypt the whole disk, make frequent whole disk images.
  2. Verify that you can open and browse that encrypted backup. If you can, restore an image to another HDD and confirm that your password works from that drive. [An employer for whom I worked zealously backed up all machines daily... only to find that none were usable when needed.]
  3. There are many excellent disk imaging applications that can schedule backups.
    • For Windows, try Macrium Reflect or others. Windows has the Volume Shadow Copy Service, which takes a self-consistent snapshot of a partition, allowing for imaging a drive while it's in use (not exactly optimal, however).
    • Mac OS apparently also has tools to schedule disk imaging,though I don't know if any can be run while the disk is mounted. [Comments are welcome!]
    • Linux, AFAIK, requires the drive being imaged to be unmounted, though check the utilities for more information. Scheduling an image while the machine is in use is problematical. [Again, comments/corrections are appreciated.]
    • In any case, a full disk image made by one OS can restore all partitions, so you only need effective backup/restore tools for one OS.