Trustpilot challenge: crack AES encrypted message

17 Jul 2014

(See also TrustpilotAesChallenge on Playground for implementations in Golang, C#, and F# and benchmarks.)

Yesterday I came across a job ad coding challenge posted by Trustpilot, a Danish company looking to hire developers. According to the company, traditional ads result in too many unqualified applicants. So in order to submit a resume, first you must decrypt a message to learn how:

From the problem statement, we can learn that a brute-force approach is the only option. Assuming that each of the first six bytes of the 32 byte key is in the closed interval from zero to 16, the search space consists of 17^6 or 24,137,569 possible keys.

Using F#, we can construct a program to try each of the 17^6 keys in sequence. As each candidate key will return a (gibberish) clear text result, the trick is knowing what success looks like. Based on a guess, we assume that somewhere in the clear text, the word "trust" (as in "trustpilot") will be present.

namespace TrustpilotChallenge

open System
open System.IO
open System.Security.Cryptography

module Cryptography =
    let aes = new AesManaged(BlockSize = 128, KeySize = 256, Padding = PaddingMode.Zeros)

    let decryptStringFromBytes (cipherText: byte[]) key iv =
        let decryptor = aes.CreateDecryptor(key, iv)
        use ms = new MemoryStream(cipherText)
        use cs = new CryptoStream(ms, decryptor, CryptoStreamMode.Read)
        use sr = new StreamReader(cs)

module Program =
    let main args =
        let cipherText = Convert.FromBase64String("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")
        let iv = Convert.FromBase64String("DkBbcmQo1QH+ed1wTyBynA==")
        let key: byte[] = Array.zeroCreate 32

        for a in [0uy..16uy] do
            for b in [0uy..16uy] do
                for c in [0uy..16uy] do
                    for d in [0uy..16uy] do
                        for e in [0uy..16uy] do
                            for f in [0uy..16uy] do
                                key.[0] <- a
                                key.[1] <- b
                                key.[2] <- c
                                key.[3] <- d
                                key.[4] <- e
                                key.[5] <- f

                                let clearText = decryptStringFromBytes cipherText key iv
                                if clearText.Contains("trust") then
                                    printfn "%d %d %d %d %d %d\n%s" a b c d e f clearText

The program searches for the right key using a single thread. To parallelize the search, we could have the program accept command-line arguments describing the lower and upper bounds of the first byte. This way we could run multiple instances of the program, one for each core to evenly distribute the load. Running more instances than cores make little sense given that the program is highly CPU bound.

On my laptop with four cores running at 2.4 GHz, it takes 4 minutes and 11 seconds to traverse the entire search space. Luckily, the current approach yields only one successful candidate key.

Have a comment or question? Please drop me an email or tweet to @ronnieholm.