Remembering all of those passwords without sacrificing security

[Bernard Lerring]

Proper encryption should be lossless, or else what's the point of it if it can't be accurately decrypted. So, in effect, the file should restore exactly as it was before encryption. I've not heard of any danger of doubly encrypting a file.

[BigMac]

Proper encryption should be lossless, or else what's the point of it if it can't be accurately decrypted. So, in effect, the file should restore exactly as it was before encryption. I've not heard of any danger of doubly encrypting a file.

I see. Thanks a lot for your quick clarification.

[Bernard Lerring]

I wouldn't take my word for it: I'm not an expert. It just seems unlikely to me.

If you encrypt a file multiple times then as long as you use the correct password and software for each decryption layer you should end up with a copy of the original, unencrypted file.

Otherwise, what's the point?

[Harley997]

Cloud storage without encryption is asking for trouble. I prefer to keep my important documents/files closer to home, but if needed, encryption/decryption is as easy as using PGP.

That's why a service like MEGA is a good option for safe encrypted cloud storage but for extra security you can put your files in a truecrypt container before you upload them.

Using multiple encryption types, that is encrypting an encrypted file can sometimes lead to the inability to decrypt the originally encrypted file as encryption can sometimes make small changes to a file that would normally be unnoticeable but can be the difference between not being able to decrypt and being able to decrypt a file.   

Is that a real risk? I mean, I have read lots of people suggesting to use multiple encryption (like 7zip + truescrypt).

The chances are much smaller and it doesn't really happen very much anymore with modern encryption technology but it is still possible.