The 2007 Underhanded C Contest has a marvelous theme -- weak crypto.
The object of this year’s contest: write a short, simple C program that encrypts/decrypts a file, given a password on the command line. Don’t implement your own cipher, but use a bog-standard strong cipher from a widely available library.
Your challenge: write the code so that some small fraction of the time (between 1% and 0.01% of files, on average) the encrypted file is weak and can be cracked by an adversary without the password. The poorly encrypted file must still decrypt properly by your own software.
Other great comments:
Short programs are innocent, and more impressive. If your source file is over 200 lines, you are not likely to win. You can hide a semi truck in 300 lines of C.
Of course, there are other factors: we award points for humor value and irony. I have always been impressed with the winner of the 2004 Obfuscated V contest, who concealed an error in a vote-counting program by adding a voter-verifiable paper trail function that overflowed a buffer. That’s evil with style.
What a great idea.