CSAW 2014 Crypto200

For this challenge, we connected to a server and were given a series of prompts. All the prompts needed to be solved within 10 seconds, and we did not initially know how many there would be.

The first prompt gave us a cipher text, and told us that a famous Roman would be proud if we cracked it. This led us to believe that it was a Caesar cipher. We were able to write a Python script to connect to the server, read the cipher text, and decrypt it to plain text. As it turned out, the message was always the same, except for the key, which rotated. We sliced the plain text and sent only the key.

The server then gave us another prompt, with a different cipher text and a mostly useless prompt about length not being everything. This cipher text was encrypted with a modified box or transposition cipher. We found an online tool to solve this kind of cipher tholman.com/other/transposition. When we copied our cipher text into this website, we were able to mostly decrypt the message. However, partway through each line, the message became gibberish. We then saw that at this point, the text began to wrap around diagonally. We were able to decrypt this cipher text by hand, but we rather than try to code it into Python, we simply figured that there were a fairly small number of keys and that they rotated. Having found one key, we submitted it each time, figuring that eventually we'd get it right.

Having 'solved' the second part of this challenge, we were given the final prompt. This turned out to be a Vigenere cipher. We used CrypTool 2 to crack this cipher, and sent it to the challenge server until it matched the cipher text. We eventually got lucky, and the server gave us the flag. The winning code:

In the end, we never coded up a transposition cipher solver or a Vigenere cipher solver. Instead, we figured them out once and submitted until both flags we'd found aligned on the same round.