1. If I delete a file and sync, can I recover the deleted file?
    • Is there a deadline (e.g. only within 90 days)? Or will they keep it forever?
  2. If I made changes to the file and synced, can I access prior versions?
    • Is there a limit to how many versions I can access (either number of revisions or number of days)?
  3. Does everything I backup need to be under one directory? (Mostly useless if “yes”)
  4. Can I select a directory and have it back up everything under it automatically? (i.e. if I create a new directory or file under it, will it get synced in the future?)
  5. Can I select a directory and sync everything under it except certain folders/files? (I don’t want to back up certain temporary directories, but I still want it to pick up other new directories/files)
  6. If I deleted a file/directory and later used the cloud service to restore it, will it restore it in the original location?
  7. If I deleted a directory that had a whole hierarchy under it, can I restore the directory and its contents and maintain the tree structure?
  8. If I deleted a directory that had a whole hierarchy under it, can I restore the a single file that was deep inside?
  9. If I have different files called abc.txt throughout my hard drive, and I deleted a bunch of them, will I be able to restore the correct one(s)?
  10. If you have the same (large) file in multiple directories, will it back all of them individually, or does it support deduplication?
  11. If only the permissions or time stamps of a file have changed, will it back up the whole file all over again?
  12. Are the files stored encrypted, and does the company have a way to get around the encryption, or can only you encrypt it?
    • While maintaining all the other features (deduplication, versioning, etc)?
  13. Can I select a file/directory and share it with a random person on the Internet?

I am surprised at how often I encounter tech folks who have not asked a significant number of these questions. Many (most?) of the well known cloud services fare poorly. SpiderOak checks most of the boxes above.