Brute forcing DES with a weak key

▼魔方 西西 提交于 2020-01-01 04:27:06

问题


I am taking a course on Cryptography and am stuck on an assignment. The instructions are as follows:

The plaintext plain6.txt has been encrypted with DES to encrypt6.dat using a 64-bit key given as a string of 8 characters (64 bits of which every 8th bit is ignored), all characters being letters (lower-case or upper-case) and digits (0 to 9).

To complete the assignment, send me the encryption key before February 12, 23.59.

Note: I expect to get an 8-byte (64-bits) key. Each byte should coincide with the corresponding byte in my key, except for the least significant bit which is not used in DES and thus, could be arbitrary.

Here is the code to my first attempt in Python:

import time
from Crypto.Cipher import DES

class BreakDES(object):
    def __init__(self, file, passwordLength = 8, testLength = 8):
        self.file = file
        self.passwordLength = passwordLength
        self.testLength = testLength
        self.EncryptedFile = open(file + '.des')
        self.DecryptedFile = open(file + '.txt')
        self.encryptedChunk = self.EncryptedFile.read(self.testLength)
        self.decryptedChunk = self.DecryptedFile.read(self.testLength)
        self.start = time.time()
        self.counter = 0
        self.chars = range(48, 58) + range(65, 91) + range(97, 123)
        self.key = False
        self.broken = False

        self.testPasswords(passwordLength, 0, '')

        if not self.broken:
            print "Password not found."

        duration = time.time() - self.start

        print "Brute force took %.2f" % duration
        print "Tested %.2f per second" % (self.counter / duration)

    def decrypt(self):
        des = DES.new(self.key.decode('hex'))
        if des.decrypt(self.encryptedChunk) == self.decryptedChunk:
            self.broken = True
            print "Password found: 0x%s" % self.key
        self.counter += 1

    def testPasswords(self, width, position, baseString):
            for char in self.chars:
                if(not self.broken):
                    if position < width:
                        self.testPasswords(width, position + 1, baseString + "%c" % char)
                        self.key = (baseString + "%c" % char).encode('hex').zfill(16)
                        self.decrypt()

# run it for password length 4
BreakDES("test3", 4)

I am getting a speed of 60.000 tries / second. A password of 8 bytes over 62 characters gives 13 trillion possibilities, which means that at this speed it would take me 130 years to solve. I know that this is not an efficient implementation and that I could get better speeds in a faster language like C or it's flavors, but I have never programmed in those. Even if I get a speed-up of 10, we're still a huge leap away from 10,000,000,000 per second to get in the hours range.

What am I missing? This is supposed to be a weak key :). Well, weaker than the full 256 character set.

EDIT

Due to some ambiguity about the assignment, here is the full description and some test files for calibration: http://users.abo.fi/ipetre/crypto/assignment6.html

EDIT 2

This is a crude C implementation that gets around 2.000.000 passwords/s per core on an i7 2600K. You have to specify the first character of the password and can manually run multiple instances on different cores/computers. I managed to solve the problem using this within a couple of hours on four computers.

#include <stdio.h>      /* fprintf */
#include <stdlib.h>     /* malloc, free, exit */
#include <unistd.h>
#include <string.h>     /* strerror */
#include <signal.h>
#include <openssl/des.h>

static long long unsigned nrkeys = 0; // performance counter

char *
Encrypt( char *Key, char *Msg, int size)
{
        static char*    Res;
        free(Res);
        int             n=0;
        DES_cblock      Key2;
        DES_key_schedule schedule;
        Res = ( char * ) malloc( size );
        /* Prepare the key for use with DES_ecb_encrypt */
        memcpy( Key2, Key,8);
        DES_set_odd_parity( &Key2 );
        DES_set_key_checked( &Key2, &schedule );
        /* Encryption occurs here */
        DES_ecb_encrypt( ( unsigned char (*) [8] ) Msg, ( unsigned char (*) [8] ) Res,
                           &schedule, DES_ENCRYPT );
        return (Res);
}

char *
Decrypt( char *Key, char *Msg, int size)
{
        static char*    Res;
        free(Res);
        int             n=0;
        DES_cblock      Key2;
        DES_key_schedule schedule;
        Res = ( char * ) malloc( size );
        /* Prepare the key for use with DES_ecb_encrypt */
        memcpy( Key2, Key,8);
        DES_set_odd_parity( &Key2 );
        DES_set_key_checked( &Key2, &schedule );
        /* Decryption occurs here */
        DES_ecb_encrypt( ( unsigned char (*) [8]) Msg, ( unsigned char (*) [8]) Res,
                           &schedule, DES_DECRYPT );
        return (Res);
}

void ex_program(int sig);

int main(int argc, char *argv[])
{
    (void) signal(SIGINT, ex_program);

    if ( argc != 4 ) /* argc should be 2 for correct execution */
    {
        printf( "Usage: %s ciphertext plaintext keyspace \n", argv[0] );
        exit(1);
    }

    FILE *f, *g;
    int counter, i, prime = 0, len = 8;
    char cbuff[8], mbuff[8];
    char letters[] = "02468ACEGIKMOQSUWYacegikmoqsuwy";
    int nbletters = sizeof(letters)-1;
    int entry[len];
    char *password, *decrypted, *plain;

    if(atoi(argv[3]) > nbletters-2) {
        printf("The range must be between 0-%d\n", nbletters-2);
        exit(1);
    }
    prime = atoi(argv[1])

    // read first 8 bytes of the encrypted file
    f = fopen(argv[1], "rb");
    if(!f) {
        printf("Unable to open the file\n");
        return 1;
    }
    for (counter = 0; counter < 8; counter ++) cbuff[counter] = fgetc(f);
    fclose(f);

    // read first 8 bytes of the plaintext file
    g = fopen(argv[2], "r");
    if(!f) {
        printf("Unable to open the file\n");
        return 1;
    }
    for (counter = 0; counter < 8; counter ++) mbuff[counter] = fgetc(g);
    fclose(g);

    plain = malloc(8);
    memcpy(plain, mbuff, 8);

    // fill the keys
    for(i=0 ; i<len ; i++) entry[i] = 0;
    entry[len-1] = prime;

    // loop until the length is reached
    do {
        password = malloc(8);
        decrypted = malloc(8);

        // build the pasword
        for(i=0 ; i<len ; i++) password[i] = letters[entry[i]];
        nrkeys++;

        // end of range and notices
        if(nrkeys % 10000000 == 0) {
            printf("Current key: %s\n", password);
            printf("End of range ");
            for(i=0; i<len; i++) putchar(letters[lastKey[i]]);
            putchar('\n');
        }

        // decrypt
        memcpy(decrypted,Decrypt(password,cbuff,8), 8);

        // compare the decrypted with the mbuff
        // if they are equal, exit the loop, we have the password
        if (strcmp(mbuff, decrypted) == 0)
        {
            printf("We've got it! The key is: %s\n", password);
            printf("%lld keys searched\n", nrkeys);
            exit(0);
        }

        free(password);
        free(decrypted);

        // spin up key until it overflows
        for(i=0 ; i<len && ++entry[i] == nbletters; i++) entry[i] = 0;
    } while(i<len);

    return 0;
}

void ex_program(int sig) {
 printf("\n\nProgram terminated %lld keys searched.\n", nrkeys);
 (void) signal(SIGINT, SIG_DFL);
 exit(0);
}

回答1:


I would assume the desired solution is to actually implement the algorithmn. Then, since your're decrypting yourself, you can bail early, which, assuming the plain text is also A-Za-z0-9, gives you a 98% chance of being able to stop after decrypting a single byte, a 99.97% chance of stoping after decrypting 2 bytes, and a 99.9995% chance of stopping after 3 bytes.

Also, use C or Ocaml or something like that. You're probably spending MUCH more time doing string manipulation than you are doing cryption. Or, at least use multi-processing and spin up all your cores...




回答2:


There is an obvious factor 256 speedup: One bit per byte isn't part of the key. DES has only a 56 bit key, but one passes in 64 bits. Figure out which bit it is, and throw away equivalent characters.




回答3:


I've had quite a bit of help and this is a solution in C. As I am a C beginner, it's probably full of bugs and bad practice, but it works.

As CodeInChaos figured out, only 31 characters need to be tested, because DES ignores every 8th bit of the key, making for example ASCII characters b: *0110001*0 and c: *0110001*1 identical in encryption/decryption when used as a part of the key.

I am using the OpenSSL library for DES decryption. On my machine the speed it achieves is ~1.8 million passwords per second, which puts the total time to test the entire key space to around 5 days. This falls a day short of the deadline. A lot better than the Python code above which is in the years territory.

There is still room for improvement, probably the code could be optimized and threaded. If I could use all my cores I estimate the time would go down to a bit more than a day, however I have no experience with threading yet.

#include <stdio.h>
#include <unistd.h>
#include <string.h>
#include <signal.h>
#include <openssl/des.h>

static long long unsigned nrkeys = 0; // performance counter

char *
Encrypt( char *Key, char *Msg, int size)
{
        static char*    Res;
        free(Res);
        int             n=0;
        DES_cblock      Key2;
        DES_key_schedule schedule;
        Res = ( char * ) malloc( size );
        /* Prepare the key for use with DES_ecb_encrypt */
        memcpy( Key2, Key,8);
        DES_set_odd_parity( &Key2 );
        DES_set_key_checked( &Key2, &schedule );
        /* Encryption occurs here */
        DES_ecb_encrypt( ( unsigned char (*) [8] ) Msg, ( unsigned char (*) [8] ) Res,
                           &schedule, DES_ENCRYPT );
         return (Res);
}

char *
Decrypt( char *Key, char *Msg, int size)
{
        static char*    Res;
        free(Res);
        int             n=0;
        DES_cblock      Key2;
        DES_key_schedule schedule;
        Res = ( char * ) malloc( size );
        /* Prepare the key for use with DES_ecb_encrypt */
        memcpy( Key2, Key,8);
        DES_set_odd_parity( &Key2 );
        DES_set_key_checked( &Key2, &schedule );
        /* Decryption occurs here */
        DES_ecb_encrypt( ( unsigned char (*) [8]) Msg, ( unsigned char (*) [8]) Res,
                           &schedule, DES_DECRYPT );
        return (Res);
}

void ex_program(int sig);

int main()
{
    (void) signal(SIGINT, ex_program);

    FILE *f, *g; // file handlers
    int counter, i, len = 8; // counters and password length
    char cbuff[8], mbuff[8]; // buffers
    char letters[] = "02468ACEGIKMOQSUWYacegikmoqsuwy"; // reduced letter pool for password brute force
    int nbletters = sizeof(letters)-1;
    int entry[len];
    char *password, *decrypted;

    // read first 8 bytes of the encrypted file
    f = fopen("test2.dat", "rb");
    if(!f) {
        printf("Unable to open the file\n");
        return 1;
    }
    for (counter = 0; counter < 8; counter ++) cbuff[counter] = fgetc(f);
    fclose(f);

    // read first 8 bytes of the plaintext file
    g = fopen("test2.txt", "r");
    if(!f) {
        printf("Unable to open the file\n");
        return 1;
    }
    for (counter = 0; counter < 8; counter ++) mbuff[counter] = fgetc(g);
    fclose(g);

    // fill the initial key
    for(i=0 ; i<len ; i++) entry[i] = 0;

    // loop until the length is reached
    do {
        password = malloc(8);
        decrypted = malloc(8);

        // build the pasword
        for(i=0 ; i<len ; i++) password[i] = letters[entry[i]];
        nrkeys++;

        if(nrkeys % 10000000 == 0) {
            printf("Current key: %s\n", password);
        }

        // decrypt
        memcpy(decrypted,Decrypt(password,cbuff,8), 8);

        // compare the decrypted with the mbuff
        // if they are equal, exit the loop, we have the password
        if (strcmp(mbuff, decrypted) == 0)
        {
            printf("We've got it! The key is: %s\n", password);
            printf("%lld keys searched", nrkeys);
            exit(0);
        }

        free(password);
        free(decrypted);

        // spin up key until it overflows
        for(i=0 ; i<len && ++entry[i] == nbletters; i++) entry[i] = 0;
    } while(i<len);

    return 0;
}

void ex_program(int sig) {
 printf("\n\nProgram terminated %lld keys searched.\n", nrkeys);
 (void) signal(SIGINT, SIG_DFL);
 exit(0);
}



回答4:


I can't help but notice the wording of the assignment: you are not actually requested to provide a DES implementation or cracker yourself. If that is indeed the case, why don't you take a look at tools such as John the Ripper or hashcat.




回答5:


This answer may be complementary to other more specific suggestions but the first thing you should do is run a profiler.

There are really nice examples here:

How can you profile a python script?

EDIT:

For this particular task, I realize it will not help. A trial frequency of 10 GHz is... Hard on a single machine with frequency less than that. Perhaps you could mention what hardware you have available. Also, don't aim for running it during a few hours. When you find a method that gives a reasonable probability of success within the week you have then let it run while improving your methods.



来源:https://stackoverflow.com/questions/9119046/brute-forcing-des-with-a-weak-key

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