So I'm curious about a few aspects of compressed files (Zip, rar, 7z, etc), and how they impact hack-ability. There is enough on this subject that I'm not clear about (since this isn't a career of mine, and I don't know too much about coding) that I'd like to ask a few questions all-together. You can skip down to the questions now if you want, but a bit of context can't hurt. I've done some research on encryption and file compression, but what I learned was more technical rather than action-reaction.
What I Know
I know that the method used to hack into a file depends largely on the hacker. I'm only aware of two methods of doing so.
1. -Password generators (Basically a program spits out every combination of password possible, starting from 1 character and increasing).
2. -Forced entry (I have little to no knowledge on this one. I can only assume that the hacker has intimate understanding of the encryption method, like AES for zip, then reverse engineers that to force entry into the encrypted folder without worrying about the password).
Lets assume that all methods of hacking/cracking into this compressed folder are available to our theoretical hacker. Let's assume that the hacker has no previous knowledge of my password, and that there was no spyware or key-loggers on my computer. The hacker has no intimate knowledge of me so he doesn't simply have the ability to guess my password or make an inference.
In the first scenario, if the hacker encounters a single zipped or otherwise compressed folder which is password protected, then a single file inside that folder (lets say the file is a notepad file with my credit card information in it), how might he go about hacking into that, what are his options here?
Then, in scenario number two, he encounters a multi layered folder; 3 password protected zips before reaching the file containing valuable information. Each password is different, so theoretically the password cracker would take 3 times as long. How might he go about his hack now?
And in the final scenario, there are at least 5 different layers, but each level gets more complex. If you were to map out the various paths possible, it would look more like a tree now rather than a straight line down. Also, the person who zipped this thing replaced/removed some of the file name extensions, so instead of the files being called "Folder.zip" they are now called something like "Folder.psd", "Folder.png", or "Folder.bat", something a bit more deceptive. The person who zipped this might have also diversified the file extensions, he sprinkled in a few zips, a few rars, a few 7zs and others. He switched their names too, so "Folder.zip" might be named "Folder.rar" or it might be named "Folder.zip", but the hacker doesn't know on the onset. The person who packed it also added some dummy files, and some "fluff" in the empty folders to make it seem like they contained valuable data instead of just being empty. This thing is labyrinthine, it's menacing, it employs long passwords and many different compression types. It's got misleading file extensions that aren't obvious at first. it's meant to seem predictable at first, but then just becomes more difficult if not impossible.
1. -Does using multiple layers of compression slow the hacker down?
2. -Does the length and complexity of a password slow the hacker down?
3. -Does changing the file extension name slow the hacker down? I'm not aware of software out there that identifies the file type, and I'm not sure if by looking at the code, he is able to discern the file type himself (or in what way he would be looking at the code).
4. -If the file is named "Folder.rar" but it's actually a "Folder.7z" file, will this slow down the hacker? Will he continuously attempt to breach the file without having any knowledge of his error?
5. -If a folder has multiple compressions and routes, like the one depicted in scenario 3, does a hacker necessarily have to go down all of those routes? Or does he have a way of circumventing or automatically getting to the desired file? I would assume that if the encryption method like AES is compromised, then the hacker could just jump through each folder without even knowing the password.
(In case you're curious about how these questions could relate to people in general, they pertain to such circumstances as archival, computer sharing, the use of cloud and external storages, and the protecting of valuable/sensitive data)