Password Protection

Nearly all modern multiuser computer and network operating systems employ passwords at the very least to protect and authenticate users accessing computer and/or network resources. But passwords are not typically kept on a host or server in plaintext, but are generally encrypted using some sort of hash scheme.


A) /etc/passwd file

 carol:FM5ikbQt1K052:502:100:Carol Monaghan:/home/carol:/bin/bash
 alex:LqAi7Mdyg/HcQ:503:100:Alex Insley:/home/alex:/bin/bash
 gary:FkJXupRyFqY4s:501:100:Gary Kessler:/home/gary:/bin/bash
 todd:edGqQUAaGv7g6:506:101:Todd Pritsky:/home/todd:/bin/bash
 josh:FiH0ONcjPut1g:505:101:Joshua Kessler:/home/webroot:/bin/bash

B.1) /etc/passwd file (with shadow passwords)

 carol:x:502:100:Carol Monaghan:/home/carol:/bin/bash
 alex:x:503:100:Alex Insley:/home/alex:/bin/bash
 gary:x:501:100:Gary Kessler:/home/gary:/bin/bash
 todd:x:506:101:Todd Pritsky:/home/todd:/bin/bash
 josh:x:505:101:Joshua Kessler:/home/webroot:/bin/bash

B.2) /etc/shadow file


FIGURE 7: Sample entries in Unix/Linux password files.

Unix/Linux, for example, uses a well-known hash via its crypt() function. Passwords are stored in the /etc/passwd file (Figure 7A); each record in the file contains the username, hashed password, user’s individual and group numbers, user’s name, home directory, and shell program; these fields are separated by colons (:). Note that each password is stored as a 13-byte string. The first two characters are actually a salt, randomness added to each password so that if two users have the same password, they will still be encrypted differently; the salt, in fact, provides a means so that a single password might have 4096 different encryptions. The remaining 11 bytes are the password hash, calculated using DES.

As it happens, the /etc/passwd file is world-readable on Unix systems. This fact, coupled with the weak encryption of the passwords, resulted in the development of the shadow password system where passwords are kept in a separate, non-world-readable file used in conjunction with the normal password file. When shadow passwords are used, the password entry in /etc/passwd is replaced with a “*” or “x” (Figure 7B.1) and the MD5 hash of the passwords are stored in /etc/shadow along with some other account information (Figure 7B.2).

Windows NT uses a similar scheme to store passwords in the Security Access Manager (SAM) file. In the NT case, all passwords are hashed using the MD4 algorithm, resulting in a 128-bit (16-byte) hash value (they are then obscured using an undocumented mathematical transformation that was a secret until distributed on the Internet). The passwordpassword, for example, might be stored as the hash value (in hexadecimal) 60771b22d73c34bd4a290a79c8b09f18.

Passwords are not saved in plaintext on computer systems precisely so they cannot be easily compromised. For similar reasons, we don’t want passwords sent in plaintext across a network. But for remote logon applications, how does a client system identify itself or a user to the server? One mechanism, of course, is to send the password as a hash value and that, indeed, may be done. A weakness of that approach, however, is that an intruder can grab the password off of the network and use an off-line attack (such as a dictionary attackwhere an attacker takes every known word and encrypts it with the network’s encryption algorithm, hoping eventually to find a match with a purloined password hash). In some situations, an attacker only has to copy the hashed password value and use it later on to gain unauthorized entry without ever learning the actual password.

An even stronger authentication method uses the password to modify a shared secret between the client and server, but never allows the password in any form to go across the network. This is the basis for the Challenge Handshake Authentication Protocol (CHAP), the remote logon process used by Windows NT.

As suggested above, Windows NT passwords are stored in a security file on a server as a 16-byte hash value. In truth, Windows NT stores two hashes; a weak hash based upon the old LAN Manager (LanMan) scheme and the newer NT hash. When a user logs on to a server from a remote workstation, the user is identified by the username, sent across the network in plaintext (no worries here; it’s not a secret anyway!). The server then generates a 64-bit random number and sends it to the client (also in plaintext). This number is thechallenge.

Using the LanMan scheme, the client system then encrypts the challenge using DES. Recall that DES employs a 56-bit key, acts on a 64-bit block of data, and produces a 64-bit output. In this case, the 64-bit data block is the random number. The client actually uses three different DES keys to encrypt the random number, producing three different 64-bit outputs. The first key is the first seven bytes (56 bits) of the password’s hash value, the second key is the next seven bytes in the password’s hash, and the third key is the remaining two bytes of the password’s hash concatenated with five zero-filled bytes. (So, for the example above, the three DES keys would be 60771b22d73c34, bd4a290a79c8b0, and9f180000000000.) Each key is applied to the random number resulting in three 64-bit outputs, which comprise the response. Thus, the server’s 8-byte challenge yields a 24-byte response from the client and this is all that would be seen on the network. The server, for its part, does the same calculation to ensure that the values match.

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. Thus, a password cracker has to break at most a 7-byte hash. One Windows NT vulnerability test program that I have used in the past will report passwords that are “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 is undoubtedly not true; all the software really has to do is look at the second 7-byte block and some known value indicates that it is empty, which would indicate a password of seven or less characters.

Consider the following example, showing the LanMan hash of two different short passwords (take a close look at the last 8 bytes):

AA: 89D42A44E77140AAAAD3B435B51404EE
AAA: 1C3A2B6D939A1021AAD3B435B51404EE

Note that the NT hash provides no such clue:

AA: C5663434F963BE79C8FD99F535E7AAD8
AAA: 6B6E0FB2ED246885B98586C73B5BFB77

It is worth noting that the discussion above describes the Microsoft version of CHAP, or MS-CHAP (MS-CHAPv2 is described in RFC 2759). MS-CHAP assumes that it is working with hashed values of the password as the key to encrypting the challenge. More traditional CHAP (RFC 1994) assumes that it is starting with passwords in plaintext. The relevance of this observation is that a CHAP client, for example, cannot be authenticated by an MS-CHAP server; both client and server must use the same CHAP version.