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I'm taking part in a capture-the-flag exercise; the level of difficulty is competent, but non-expert. I'm not a security practitioner, but I do have a development background and a reasonable knowledge of standard tools and techniques.

One task involves a number of steps to recover an encrypted zip file, which I have done. The zip then contains a single file, flag.txt - the target. The final step is to break the encryption.

The zip file is small, 190 bytes in total, and analysis of the zip file header with a hex editor shows it was created with the v2.0 PKzip format (which I understand is relatively insecure). The target file itself is 28 bytes long.

I've run a dictionary attack with the rockyou wordlist, and a brute-force attack of the full lowercase/uppercase/numeric/special character set up to five characters, without any luck (both with fcrackzip on kali Linux). The challenge is not at a level where we should be using specialist kit (e.g. GPU-based cracking), so if brute-force was the answer then i'd expect a very simple password.

So I must be missing a trick. Can anybody suggest what it could be? I'm aware that the PKZip v2 format has a known-plaintext attack, but I believe this is most commonly used in the case that the zip contains one or more commonly-available files (e.g. a widely-available jpg or jar file) that can be found elsewhere to provide the plaintext, and I don't have that here. Are there other attacks that I haven't found? Or is known-plaintext the only remaining answer, and I need to try and figure out what could be in the file? As I understand it, it is just about large enough for known-plaintext to be applied?

Thank you for any thoughts

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    By the way, if I create test encrypted zip files with a four-character random password or with a dictionary word from the wordlist then I can decrypt both with fcrackzip, so i'm confident that i'm using the tools correctly
    – strmqm
    Oct 14, 2017 at 11:21
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    It's very rare on a CTF to need crack a zip by brutefore. Are you sure you are not missing the "right" way to do it? Which ctf is?
    – OscarAkaElvis
    Oct 14, 2017 at 17:16
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    crypto.stackexchange.com/questions/19716/… Have a look at this Q&A at the Crypto Stackexchange.
    – vidarlo
    Oct 15, 2017 at 9:17
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    Just to wrap this up, I was indeed missing the "right" way to do it - the zip password was hidden in some traffic earlier in the pcap I grabbed the zip from. Bit obscure, but I guess I learned a lot about cracking zip files, even if I didn't need to
    – strmqm
    Nov 12, 2017 at 12:17
  • Which flags did you use for fcrackzip? I would expect capture-the-flag exercise to use very short password and I think fcrackzip assumes that the password is at least 6 characters long by default.
    – Mikko Rantalainen
    Mar 9 at 18:31

1 Answer 1

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A few suggestions:

  • Try building a dictionary based on all strings you can find on the system.
  • Check that the ZIP file really is encrypted, and not just using a dummy header.
  • Make sure the header is not corrupt, or a cracking tool may fail even if it has the right key.
  • It's possible that the key is hidden somewhere, and you have to find it to get that flag.
  • Depending on the level of access you have, the key might be in memory.

Without more information about the specific task, there's really not much anyone can do to help.

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