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At start I'll admit I'm a total newbie when it goes for stuff I want to achieve, but I'm willing to learn, so sorry in advance for writing total nonsense.

Stuff I want to achieve: I want to store my files online as a backup of them. I already have an external 2TB drive that I use for backups, but I would like to backup my backup for a good measure plus I don't put every file on the external drive so in case of "bad stuff" I would need to restore them (spend good amount of time on this). Sure I know that online/cloud (whatever it's called) storage doesn't guarantee that my files won't be deleted (in case of provider drive crash, or the company being shutdown, esp if it's a free to use service or a free account), but if cloud storage would get deleted I still have my external drive/my actual drives with files (so I can re upload them), but at the moment, if my drives would say "bye bye", well it wouldn't be a good thing :/

So how to store those files securely? What I mean about "securely" is too protect them from being sniffed or looked into by unauthorized users. I won't make those files public, but even then "users" can get access to them (cough all those leaked celebrity photos cough).

I've read I can use 7zip or WinRAR password encryption with for example a 40 digit password (that I would store in KeePass), but how secure is it? Isn't there something better or a way to make it better (better as "more secured")? For example (or what I would like to accomplish):

I have a file -> I 7zip it with AES-256 and a 40 digit password -> I get a .7zip file -> I use SoftwareX to encrypt it with a private key/another 40 digit password (1) -> I get a .ecrypted file that I upload to online storage. If I need the file, I download the .ecrypted file, decrypt it with the password/key in SoftwareX, unzip it and then I have the files I need (or more likely group of files).

Is something like that achievable? If yes - could you provide a guide or something to start off, if no - what could you suggest to achieve something similar?

I read about VeraCrypt, but the whole container/hidden disk/mounting/unmounting thing looks too complicated for me - I just want to store files (rather) securely in cloud, and the easier the creation process is the better (and vice versa, the easier restore process is the better). I also read that certain (like Google on their Google Drive) providers encrypt files but I would prefer to do the whole thing on my own.

As an example of "what do you want to store" - my music CDs that are on my shelf, I don't need to keep those on the external drive, but in case of losing the mp3 files that I've created (audio CD -> mp3) I would need to redo the whole process for every 400+ CD I've collected. But I want to store them securely, without having to think who can access them or who can delete them as "illegal copyright files". And in case of losing the mp3, I can just download the encrypted file, decrypt it, copy/paste and voila, files restored.

Thanks in advance and have a nice day!

(1) Or something similar, I have a very basic knowledge about data security, data encryption and the whole private/public key idea, so I'm more then open to suggestions on how to make the "encryption process" better (as long as the whole process requires one software to do it, multiple applications are a no-no due to complicity and possible future version problems).

foobar
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  • You state that you would like to store your files (securely) on a cloud provider service. Do you have any idea in mind what cloud service you might use for that? Also, are the files you're wanting to back up all resident on your personal Windows computer? – geofrey rainey May 19 '17 at 03:14

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Just go with one round of encryption. You are suggestion first encrypting with one program, and then with another. There is really no benefit to that. As long as you use good crypto to begin with, you're fine.

As you point out, WinRar uses AES. That is good crypto. This answer to a similar question suggests using Veracrypt instead because it has better key stretching, but if you use a long and random password that isn't an issue.

So there is nothing wrong with your original plan of just using WinRar. No need to make it more complicated than that.

Anders
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