Nathan wants to know if there's any recourse if a company isn't protecting his passwords. Leo says in Europe they have the GDPR, but in the US the only real protection is through HIPPA in the medical field. Leo recommends talking to Brian Krebbs at Krebbs on Security and asking him how he should write a letter to warn them of their liability.
Brian's doctor is sending him emails that are encrypted. He's supposed to click on a link and then log into GoDaddy to see it, but it doesn't really work. Leo says the doctor is sending the additional security to maintain HIPPA compliance and he's using a third party encryption to do it. Since it's not really accessible to Brian because he's blind, Leo says he should advise them that it isn't working. Leo advises GPG, public key crypto. It uses one key to encrypt, and another to decrypt. Once it's set up, it's outstanding and safe.
Robert is a college professor and he wants to take all his desktop files and put them in the cloud, syncing them with his laptop and desktop computers. Leo says there's several ways to accomplish that goal. ICloud will do it if you have a Mac. Both Microsoft's OneDrive and DropBox will do it for both Windows and Mac. Leo says that DropBox is probably the simplest way to go about it. The Chatroom says that Box.net is hipping compliant as well.