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Note that these sites search databases and/or use rainbow tables to find a suitable string that produces the hash in question but one can't definitively guarantee what string originally produced the hash. This is an important distinction. Suppose that you want to crack someone's password, where the hash of the password is stored on the server. Indeed, all you then need is a string that produces the correct hash and you're in! However, you cannot prove that you have discovered the user's password, only a "duplicate key."

In cryptography, size does matter. The larger the key, the harder it is to crack a block of encrypted data. The reason that large keys offer more protection is almost obvious; computers have made it easier to attack ciphertext by using brute force methods rather than by attacking the mathematics (which are generally well-known anyway). With a brute force attack, the attacker merely generates every possible key and applies it to the ciphertext. Any resulting plaintext that makes sense offers a candidate for a legitimate key. This was the basis, of course, of the EFF's attack on DES.

There is, however, a significant weakness to this system. Specifically, the response is generated in such a way as to effectively reduce 16-byte hash to three smaller hashes, of length seven, seven, and two, respectively. Thus, a password cracker has to break at most a 7-byte hash. One Windows NT vulnerability test program that I used in the past reported passwords that were "too short," defined as "less than 8 characters." When I asked how the program knew that passwords were too short, the software's salespeople suggested to me that the program broke the passwords to determine their length. This was, in fact, not the case at all; all the software really had to do was to look at the last eight bytes of the Windows NT LanMan hash to see that the password was seven or fewer characters.

The second DES Challenge II lasted less than 3 days. On July 17, 1998, the Electronic Frontier Foundation (EFF) announced the construction of hardware that could brute-force a DES key in an average of 4.5 days. Called Deep Crack, the device could check 90 billion keys per second and cost only about $220,000 including design (it was erroneously and widely reported that subsequent devices could be built for as little as $50,000). Since the design is scalable, this suggests that an organization could build a DES cracker that could break 56-bit keys in an average of a day for as little as $1,000,000. Information about the hardware design and all software can be obtained from the EFF.

The Deep Crack algorithm is actually quite interesting. The general approach that the DES Cracker Project took was not to break the algorithm mathematically but instead to launch a brute-force attack by guessing every possible key. A 56-bit key yields 256, or about 72 quadrillion, possible values. So the DES cracker team looked for any shortcuts they could find! First, they assumed that some recognizable plaintext would appear in the decrypted string even though they didn't have a specific known plaintext block. They then applied all 256 possible key values to the 64-bit block (I don't mean to make this sound simple!). The system checked to see if the decrypted value of the block was "interesting," which they defined as bytes containing one of the alphanumeric characters, space, or some punctuation. Since the likelihood of a single byte being "interesting" is about ¼, then the likelihood of the entire 8-byte stream being "interesting" is about ¼8, or 1/65536 (½16). This dropped the number of possible keys that might yield positive results to about 240, or about a trillion.

In March 2016, the SSL DROWN (Decrypting RSA with Obsolete and Weakened eNcryption) attack was announced. DROWN works by exploiting the presence of SSLv2 to crack encrypted communications and steal information from Web servers, email servers, or VPN sessions. You might have read above that SSLv2 fell out of use by the early 2000s and was formally deprecated in 2011. This is true. But backward compatibility often causes old software to remain dormant and it seems that up to one-third of all HTTPS sites at the time were vulnerable to DROWN because SSLv2 had not been removed or disabled.

Having nothing to do with TrueCrypt, but having something to do with plausible deniability and devious crypto schemes, is a new approach to holding password cracking at bay dubbed Honey Encryption. With most of today's crypto systems, decrypting with a wrong key produces digital gibberish while a correct key produces something recognizable, making it easy to know when a correct key has been found. Honey Encryption produces fake data that resembles real data for every key that is attempted, making it significantly harder for an attacker to determine whether they have the correct key or not; thus, if an attacker has a credit card file and tries thousands of keys to crack it, they will obtain thousands of possibly legitimate credit card numbers. See "'Honey Encryption' Will Bamboozle Attackers with Fake Secrets" (Simonite) for some general information or "Honey Encryption: Security Beyond the Brute-Force Bound" (Juels & Ristenpart) for a detailed paper.

As a slight aside, another way that people try to prove that their new crypto scheme is a good one without revealing the mathematics behind it is to provide a public challenge where the author encrypts a message and promises to pay a sum of money to the first person — if any — who cracks the message. Ostensibly, if the message is not decoded, then the algorithm must be unbreakable. As an example, back in ~2011, a $10,000 challenge page for a new crypto scheme called DioCipher was posted and scheduled to expire on 1 January 2013 — which it did. That was the last that I heard of DioCipher. I leave it to the reader to consider the validity and usefulness of the public challenge process. 2b1af7f3a8