Chapter 14

Section: Part IV:  The Defender's Toolkit

Chapter 14. Password Crackers


        An Introduction to Password Cracking

        The Password-Cracking Process

        The Password Crackers

        Password Crackers for Windows NT

        UNIX Password Cracking

        Cracking Cisco, Application, and Other Password Types

        Other Resources

This chapter examines password crackers and other programs designed to circumvent password security. Although password cracking is a core skill of most intruders, it is also important for system and network administrators to understand the INs and OUTs of password security. Comprehending where and why passwords can fail is paramount in maintaining enterprise security; many times, passwords are the first and unfortunately only lines of defense. This chapter explains how passwords are stored, how they can be stolen, how they are cracked, and what you can do to minimize the risks associated with using passwords.


Section: Chapter 14.  Password Crackers

An Introduction to Password Cracking

Passwords and "pass phrases" are used for everything ranging from logging into terminals to checking email accounts, from protecting Excel spreadsheets to securing the encryption keys for PKI-enabled enterprise networks. Their use in the enterprise is widespread, to say the least.

Password crackers are programs that aid in the discovery of protected passwords, usually through some method of automated guessing. Although some applications and poorly designed infrastructure equipment will encrypt or encode passwords, most modern day operating systems and devices create a hash of the password instead. I will go into the differences between hashing and encrypting in the next section, but for now simply note that they are two different methods of storing password information.

Although some poor encryption mechanisms can be easily reversed, modern day hashing methods are one-way that is, they can not be reversed and therefore decryption is not an option. Although the use of one-way algorithms can sound like a rock-solid solution, it simply makes the task at hand a little more time consuming. To circumvent the challenges created by hashing, password crackers simply employ the same algorithm used to encrypt the original password. The tools perform comparative analysis (a process explained later in this chapter), and simply try to match their guesses with the original encrypted phrase or password hash.

Many password crackers are nothing but guessing engines, programs that try word after word, often at high speeds. These programs rely on the theory that eventually you will encounter the right word or phrase. This theory is sound because humans are lazy creatures. They rarely take the trouble to create strong passwords. However, this shortcoming is not always the user's fault:

Users are rarely, if ever, educated as to what are wise choices for passwords. If a password is in the dictionary, it is extremely vulnerable to being cracked, and users are simply not coached as to "safe" choices for passwords. Of those users who are so educated, many think that simply because their password is not in /usr/dict/words, it is safe from detection. Many users also say that because they do not have private files online, they are not concerned with the security of their account, little realizing that by providing an entry point to the system they allow damage to be wrought on their entire system by a malicious cracker.

A Survey of, and Improvements to, Password Security. Daniel V. Klein, Software Engineering Institute, Carnegie-Mellon University, Pennsylvania. (PostScript creation date reported: February 22, 1991.)

It should be noted, however, that the raw "It's-not-in-the-dictionary" approach is now somewhat misleading as well. Password-cracking dictionaries now contain hundreds of thousands of popular names, characters, musical bands, slang, expletives, and an assortment of culturally popular terms that might or might not be in a classic dictionary. We'll explore the depth and versatility of password guessing later on, but the new rule of thumb is to avoid any kind of word all together. For example, "808state" is easily guessed by most password crackers, not only because it's based on a word (state) and a number (808), but also because it's the name of a popular band out of Manchester, England. Stronger passwords can be created by using a combination of letters, numbers, and extended characters. Acronyms work wonderfully, for example, "I'm trying to learn information security techniques quickly!" could be translated to "IT2LISTQ!". This is a MUCH harder password to guess, but is not all that difficult to remember.

The simple password problem is a persistent one despite the fact that it is easy to provide password-security education. It's puzzling how such a critical security issue (which can easily be addressed) is often overlooked. The issue goes to the very core of security:

Exploiting ill-chosen and poorly-protected passwords is one of the most common attacks on system security used by crackers. Almost every multiuser system uses passwords to protect against unauthorized logons, but comparatively few installations use them properly. The problem is universal in nature, not system-specific; and the solutions are simple, inexpensive, and applicable to any computer, regardless of operating system or hardware. They can be understood by anyone, and it doesn't take an administrator or a systems programmer to implement them.

"Understanding Password Security for Users On and Offline." K. Coady. New England Telecommuting Newsletter, 1991.


One additional password pitfall that is frequently overlooked is the password overload scenario. If users have a multitude of passwords to remember, there is a greater chance that they will write them down, use weaker passwords, or introduce an assortment of other insecure password practices into your environment. This is where centralized authentication systems, directory services, and single-sign on solutions can help you. Not only do they reduce operating costs and complexity, they ultimately help you with your overall security posture.


Password Cryptography 101

The etymological root of the word cryptography is instructive. The word crypto stems from the Greek word kryptos. Kryptos describes anything that is hidden, obscured, veiled, secret, or mysterious. The word graph is derived from graphia, which means writing. Thus, cryptography is the art of secret writing. Yaman Akdeniz, in his paper Cryptography and Encryption, gives an excellent and concise definition of cryptography:

Cryptography, defined as "the science and study of secret writing," concerns the ways in which communications and data can be encoded to prevent disclosure of their contents through eavesdropping or message interception, using codes, ciphers, and other methods, so that only certain people can see the real message.

"Cryptography and Encryption." Yaman Akdeniz. Cyber-Rights & Cyber-Liberties (UK), August 1996, at Criminal Justice Studies of the Law Faculty of University of Leeds, Leeds LS2 9JT.

To illustrate the process of cryptography, I'll reduce it to its most fundamental parts. Imagine that you created your own code in which each letter of the alphabet corresponds to a number (see Figure 14.1).

Figure 14.1. A primitive example of a code.


Figure 14.1 shows part of a table, or legend. Below each letter is a corresponding number. A = 7, B = 2, and so forth. This is a code of sorts. If you write a message using these rules, only you and the recipient will know what the message really says.

Unfortunately, such a code can be easily broken. For example, if each letter has a fixed numeric counterpart, you will only use 26 different numbers (perhaps 1 through 26, although you could choose arbitrary numbers). Lexical analysis would reveal your code within a few seconds. (Some software programs perform such analysis at high speed, searching for patterns common to your language.)


Another slightly more complex method is to make each letter become another letter, based on a standard incremental or decremental operation. One system that works this way is ROT-13 encoding. In ROT-13, a substitute letter is used. Moving 13 letters ahead (see Figure 14.2) in the chosen alphabet derives the substitute letter.

Figure 14.2. The ROT-13 system of letter substitution.


This, too, is an ineffective method of encoding or encrypting a message (although it worked in Roman times for Caesar, who used a shift-by-three formula). Some programs quickly identify this pattern. However, this doesn't mean that techniques such as ROT-13 are useless. I will illustrate why, and in the process, I can demonstrate the first important point about encryption:

Any form of encryption can be useful, given particular circumstances. These circumstances might depend upon time, the sensitivity of the information, and from whom you wish to hide data.

In other words, techniques such as ROT-13 can be quite useful under the right circumstances. Here's an example: Suppose a cracker wants to post a new cracking technique to Usenet. He's found a hole and wants to publicize it while it's still exploitable. To prevent security specialists from discovering that hole as quickly as the crackers, the cracker uses ROT-13 to encode his message.

There are a number of organizations that download Usenet traffic on a wholesale basis. In this way, they gather information about the cracker community. Some organizations even use popular search engines to ferret out cracker techniques. These search engines employ regex (regular expression) searches (that is, they search by word or phrase). For example, the searching party enters a combination of words such as





When this combination of words is entered correctly, a wealth of information emerges. However, if the cracker uses ROT-13, search engines will miss the post. For example, the message

Guvf zrffntr jnf rapbqrq va EBG-13 pbqvat. Obl, qvq vg ybbx fperjl hagvy
jr haeniryrq vg!

is beyond the reach of the average search engine. What it really looks like is this:

This message was encoded in ROT-13 coding. Boy, did it look screwy until
we unraveled it!

Most modern mail and newsreaders support ROT-13 encoding and decoding (Free Agent by Forte is one; Netscape Communicator's Mail package is another). Again, this is a rudimentary form of encoding something, but it demonstrates the concept. Now, let's get a bit more specific.

DES and Crypt

Today, Internet information servers run many different operating systems. However, for many years, UNIX was the only game in town. The greater number of password crackers were designed to crack UNIX passwords. Let's start with UNIX, then, and work our way forward.

In UNIX, all user login IDs and passwords are centrally stored in either one of two files: the passwd file, usually found in the /etc directory, or a file called shadow, also located in the /etc directory. These files contain various fields. Of those, we are concerned with two: the login ID and the hashed password.


Using "shadow passwords" is the preferred way of storing password hashes. The /etc/shadow file is only accessible by the root account and system services, as opposed to /etc/passwd, which is readable by everyone. If you have any systems that are still storing password hashes in /etc/passwd, either upgrade them to shadow passwords or remove them from your environment as soon as possible.


The login ID is stored in plain text, or humanly readable English. The password is stored in encrypted form. The encryption process is performed using Crypt(3), a program based on the data encryption standard (DES).

IBM developed the earliest version of DES; today, it is used on all UNIX platforms for password encryption. DES is endorsed jointly by the National Bureau of Standards and the National Security Agency. In fact, since 1977, DES has been the generally accepted method for safeguarding sensitive data. Figure 14.3 contains a brief timeline of DES development.

Figure 14.3. A brief timeline of the development of DES.


DES was developed to protect certain nonclassified information that might exist in federal offices, as set forth in Federal Information Processing Standards Publication 74, Guidelines for Implementing and Using the NBS Data Encryption Standard:

Because of the unavailability of general cryptographic technology outside the national security arena, and because security provisions, including encryption, were needed in unclassified applications involving Federal Government computer systems, NBS initiated a computer security program in 1973 which included the development of a standard for computer data encryption. Because Federal standards impact on the private sector, NBS solicited the interest and cooperation of industry and user communities in this work.

Information about the original mechanical development of DES is scarce. Reportedly, at the National Security Agency's request, IBM made certain documents classified. However, the source code for Crypt(3) (the current implementation of DES in UNIX) is widely available. This is significant because in all the years that source has been available for Crypt, no one has yet found a way to easily reverse-encode information encrypted with it.

There are several versions of Crypt, and they work slightly differently. In general, however, the process is as follows:

1.       Your password is taken in plain text (or, in cryptographic jargon, clear text).

2.       Your password is used as a key to encrypt a series of zeros (64 in all). The resulting encoded text is thereafter referred to as cipher text, the unreadable code that results after plain text is encrypted. This cipher text is sometimes referred to as a hash, as well, but the term only loosely fits in this case.


One-way hash functions are frequently used as an alternative to actually encrypting passwords. By using hashing algorithms such as MD5 or SHA-1, a digital footprint can be created of the password that doesn't contain the actual password itself. This varies from the process of encryption because the output does not contain the original input in any form, and it is therefore impossible to derive the original input from the output. Many modern UNIX systems are moving towards the use of MD5 hashes instead of relying on the crypt/DES process. If you are interested in one-way hashing techniques, or cryptography in general, Bruce Schneier's Applied Cryptography (John Wiley & Sons, ISBN 0-471-12845-7) is a must-have.


Certain versions of Crypt, notably Crypt(3), take additional steps. For example, after going through this process, the encrypted text is again encrypted, numerous times, using the password as a key. This is a fairly strong method of encryption; it is extremely difficult to break. It is estimated, for example, that the same password can be encoded in 4,096 different ways. The average user, without any knowledge of the system, could probably spend her entire life trying to crack DES and never be successful. To get that in proper perspective, here's an estimate from the National Institute of Standards and Technology:

The cryptographic algorithm [DES] transforms a 64-bit binary value into a unique 64-bit binary value based on a 56-bit variable. If the complete 64-bit input is used (i.e., none of the input bits should be predetermined from block to block) and if the 56-bit variable is randomly chosen, no technique other than trying all possible keys using known input and output for the DES will guarantee finding the chosen key. As there are more than 70,000,000,000,000,000 (seventy quadrillion) possible keys of 56 bits, the feasibility of deriving a particular key in this way is extremely unlikely in typical threat environments.

"Data Encryption Standard (DES)," Federal Information Processing Standards Pub lication 46-2, NIST, December 30, 1993.

One might think that DES is entirely infallible. It isn't. Although the information cannot be reverse-encoded, passwords encrypted via DES can be revealed through a comparative process. The process works as follows:

1.       You obtain a dictionary file, which is really no more than a flat file (plain text) list of words (commonly referred to as wordlists).

2.       These words are encrypted using DES.

3.       Each encrypted word is compared to the target password. If a match occurs, there is a 98% chance that the password was cracked.

The process itself is both simple and brainless, yet quite effective. However, password-cracking programs made for this purpose are often times a little more clever. For example, such cracking programs often subject each word to a list of rules.

A rule could be anything, any manner in which a word might appear. Typical rules might include

        Alternate uppercase and lowercase lettering.

        Spell the word forward and then backward and then fuse the two results (for example, can becomes cannac).

        Add the number 1 to the beginning or end of each word.

Naturally, the more rules you apply, the longer the cracking process takes. However, more rules also guarantee a higher likelihood of success for a number of reasons:

        The UNIX file system is case sensitive (WORKSTATION is interpreted differently than Workstation or workstation is).

        Alternating letters and numbers in passwords is a common practice.

Password crackers have had a tremendous impact on Internet security, chiefly because they are so effective:

Crypt uses the resistance of DES to known plain text attack and make [sic] it computationally unfeasible to determine the original password that produced a given encrypted password by exhaustive search. The only publicly known technique that can reveal certain passwords is password guessing: passing large wordlists through the crypt function to see whether any match the encrypted password entries in an /etc/passwd file. Our experience is that this type of attack is successful unless explicit steps are taken to thwart it. Generally we find 30 percent of the passwords on previously unsecured systems.

UNIX Password Security Ten Years Later. David Feldmeier and Philip R. Karn. Bellcore.

Password-cracking programs are improving in their effectiveness, too. The newer programs incorporate more extensive rules and diverse wordlists. Most wordlists are plain text files with one word per line. These files range in size from 1MB to more than 20MB. Many wordlists are available on the Internet; they come in a wide variety of languages (so an English-speaking American cracker can crack an Italian machine, and vice versa).

There are several popular wordlist collections. Some are simply dictionaries, and others contain hyphenated words, uppercase and lowercase, and so on. Perhaps the most definitive collection is available on the Packetstorm Web site. Its page is


Section: Chapter 14.  Password Crackers

The Password-Cracking Process

If you're new to system administration, you're probably wondering how you can benefit from password crackers. Passwords crackers can help you identify weak passwords on your network.

Ideally, you should run a password cracker once a month. If your network supports several platforms, you might need a wide range of password-cracking utilities. Although password crackers such as John the Ripper can crack both Windows NT-based password files and UNIX-based ones, most password crackers are designed to crack only a single type of password.

To crack passwords, you need the following elements:

        Sufficient hardware (A Pentium-III based machine will do nicely)

        A password cracker (such as John the Ripper, Crack, L0phtCrack, and so on)

        A password file (/etc/shadow, the NT SAM file, and so on)

I discuss methods of grabbing password files (like the UNIX shadow file, or the Windows NT SAM file) throughout this book, and we will examine the password-cracking programs themselves in the next section. On the hardware front, however, you need only really know one thing: More is better.

Cracking passwords is a CPU- and memory-intensive task. It can take days, weeks, months, or even years depending on the strength of the password and the algorithms used. To crack passwords effectively, you need suitable hardware. The more powerful the hardware, the faster you will be able to crack even relatively strong passwords.

For cracking common password files, like those found on UNIX and Windows NT systems, I have found that to comfortably handle large password files, you should have the following resources:

        A 400Mhz Pentium II or better

        64 MB of RAM or better

A single-processor Pentium-II based system dedicated to password cracking can chew through most NT SAM (password) files in under 48 hours. Dual-processor, Pentium-III based systems (or higher) will work even faster.

There are techniques, however, for overcoming hardware restrictions. One is the parlor trick of distributed cracking. In distributed cracking, you run the cracking program simultaneously on separate processors. There are a few ways to do this. One is to break the password file into pieces and crack those pieces on separate machines. In this way, the job is distributed among a series of workstations, thus cutting resource drain and the time it takes to crack the entire file.

The problem with distributed cracking is that it makes a lot of noise. Remember the Randal Schwartz case? Mr. Schwartz probably would never have been discovered if he were not distributing the CPU load. Another system administrator noticed the heavy processor power being eaten. (He also noted that one process had been running for more than a day.) Distributed cracking really isn't viable for a cracker unless he is the administrator of a site or he has a net work at home (which is not so unusual these days; I have a network at home that consists of Windows 95, Windows NT, Linux, Sun, and Novell boxes).


Section: Chapter 14.  Password Crackers

The Password Crackers

The remainder of this chapter is devoted to individual password crackers. Some tools are made for cracking UNIX passwd and shadow files, some are for cracking NT SAM files, and some work across applications and services you might not have ever heard of. Some of the tools here are not even password crackers; instead, they are auxiliary utilities that can be used in conjunction with existing password-related tools.


Section: Chapter 14.  Password Crackers

Password Crackers for Windows NT

Windows NT keeps password hashes in a protected portion of the Registry called the SAM. However, there are a number of ways to get these hashes. The easiest method is to use the rdisk command to create a backup of the SAM, and then copy that file to a password-cracking machine. rdisk /s- will create a compressed SAM image in the repair directory of the %systemroot% (usually c:\winnt\repair).

Another trick is to sniff the password hashes off of the wire. L0phtCrack, for example, has this feature built in. Regardless of how you get the NT password hashes themselves, the following utilities can be used to aid your Windows NT-based cracking efforts.


L0phtCrack is the most celebrated NT password-cracking tool to date, primarily because it uses a two-prong approach, as explained by its authors:

Passwords are computed using 2 different methods. The first, a dictionary lookup, called dictionary-cracking, uses a user supplied dictionary file. The password hashes for all the words in the dictionary file are computed and compared against all the password hashes for the users. When there is a match the password is known. This method is extremely fast. Thousands of users can be checked with a 100,000-word dictionary file in just a few minutes on a PPro 200. The drawback to this method is that it only finds very simple passwords . The second method is the brute-force computation. This method uses a particular character set such as A Z or A Z plus 0 9 and computes the hash for every possible password made up of those characters.

When L0phtCrack was released, it caused considerable debate, especially because the pro gram's authors pointed out that Microsoft's password algorithm was "intrinsically flawed." Microsoft officials hotly disputed that claim, but their efforts were for naught. L0phtCrack works very well, and it is now an accepted fact that Windows NT's password-hashing techniques are flawed from a security standpoint.

To effectively use L0phtCrack, you need the password hashes.

L0phtCrack is located at

John the Ripper by Solar Designer

John the Ripper is one of the most diverse password crackers in circulation today. John runs on both DOS and Windows32 platforms (95, 98, NT, 2000, and so on) as well as on most flavors of UNIX. The binary distribution was released in December 1996, and the package has continued to be updated ever since.

John's real strength lies in its diversity. John can crack UNIX files natively and Windows NT SAM files with the use of pwdump. Modules have been created to attack other platforms such as LDAP and Kerberos as well. John can also perform true brute-forcing of password files that is, password cracking going beyond basic dictionary-based guessing. Brute-forcing is a technique that utilizes standard or extended character sets to literally try every combination possible. It is extremely resource intensive, and has only become practical in recent years by the rapid advances in processing power.

Penetration testers and crackers alike love John because they can perform cross-platform password cracking on a single, centralized machine. John is maintained by Solar Designer, and its home page is


NTCrack is a curious utility. As its authors explain, it isn't really intended for cracking passwords in a practical sense. However, it does demonstrate that a brute-force cracker can work against Windows NT. The program's purpose is to perform high-speed, brute-force attacks against an NT box. As reported by the folks at Somarsoft, the original maintainers of the program:

The program below [NTCrack] does about 1000 logins per minute, when run on a client 486DX-33 with 16MB of RAM, a server 486DX2-66 with 32MB of RAM, and a 10 MBps Ethernet. This is equivalent to testing 1,152,000 passwords per day. By comparison, there are perhaps 100,000 common words in the English language.

To prevent such attacks, it is suggested that you enable account lockout, rename the Administrator account, disable network logins for Administrator, and disable SMB over TCP/IP (if appropriate). You can read more about passfilt and securing Windows NT servers in Chapter 19, "Microsoft."

You can find NTCrack at

NT Accessories

The NT accessories listed in Table 14.1 are indispensable.

Table 14.1. Accessories for Use in Cracking NT Passwords


Description and Location


Samdump is a utility that automates the process of dumping NT password hashes. It dumps these values from the SAM file located either in the Registry on an emergency repair disk or off the hard disk drive. Samdump is available at


Pwdump is similar to samdump. It dumps NT usernames and passwords. (Fortunately, pwdump requires Administrator privileges.) Pwdump is available at


NTFSDOS is a tool that allows you to mount NTFS volumes and view them as though they were FAT32. You can use this tool to extract SAM password information from a NTFS drive. NTFSDOS is available at

Notes on NT Password Security

Rather than simply use the utilities described here, you might want to investigate exactly what factors led to such poor password security in NT in the first place. The following documents are excellent resources:

        A L0phtCrack Technical Rant. A detailed analysis (really, the gory details) of NT password weaknesses. Authored by

        On NT Password Security. Jos Visser. An excellent paper that discusses both the mechanical and theoretical problems with the NT password scheme. The author also discusses how to perform an attack against Windows NT password dumps.

        NT Cryptographic Password Attacks and Defences FAQ. Alan Ramsbottom. This document provides information on why certain Microsoft fixes didn't work, as well as perspective on the weakness in Microsoft's implementation of DES.


Section: Chapter 14.  Password Crackers

UNIX Password Cracking

This next section discusses the issues surrounding UNIX password cracking. Most of these programs were designed for UNIX as the hosting platform, but some of them will run on other platforms such as DOS and Windows 95. All of them are, however, designed to crack UNIX passwords.

About UNIX Password Security

UNIX password security, when implemented correctly, is fairly reliable. The main problem is that people continue to pick weak passwords. Unfortunately, because UNIX is a multiuser system, every user with a weak password represents a risk to the remaining users. This is a problem that must be addressed:

It is of utmost importance that all users on a system choose a password that is not easy to guess. The security of each individual user is important to the security of the whole system. Users often have no idea how a multiuser system works and don't realize that they, by choosing an easy-to-remember password, indirectly make it possible for an outsider to manipulate the entire system.

"UNIX Password Security." Walter Belgers. December 6, 1993.

The paper "UNIX Password Security" gives an excellent overview of exactly how DES works into the UNIX password scheme. It includes a schematic that shows the actual process of encryption using DES. For users new to security, this paper is an excellent starting point. You can find "UNIX Password Security" at

What are weak passwords? Characteristically, they are anything that might occur in a dictionary. Moreover, proper names are poor choices for passwords. However, there is no need to theorize on what passwords are easily cracked. Safe to say, if the password appears in a password-cracking wordlist available on the Internet, the password is no good.

Start your search for wordlists at

By regularly checking the strength of the passwords on your network, you can ensure that crackers cannot penetrate it (at least not through exploiting bad password choices). Such a regimen can greatly improve your system security. In fact, many ISPs and other sites now employ tools that check a user's password when it is first created. This basically implements the phi losophy that

the best solution to the problem of having easily guessed passwords on a system is to prevent them from getting on the system in the first place. If a program such as a password cracker reacts by guessing detectable passwords already in place, then although the security hole is found, the hole existed for as long as the program took to detect it . If however, the program which changes users'passwords checks for the safety and guessability before that password is associated with the user's account, then the security hole is never put in place.

Improving System Security via Proactive Password Checking. Matthew Bishop, UC Davis, California, and Daniel Klein, LoneWolf Systems Inc. Computers and Security [14, pp. 233 249], 1995.

The paper "Improving System Security via Proactive Password Checking" is probably one of the best case studies and treatments of easily guessable passwords. It treats the subject in depth, illustrating real-life examples of various passwords that you might think are secure but actually are not. You can find "Improving System Security via Proactive Password Checking" at


Crack is the de facto standard for UNIX password cracking. It was written by Alec D. E. Muffett, a UNIX software engineer in Wales. In the documentation, Muffett concisely articulated the program's purpose:

Crack is a freely available program designed to find standard UNIX eight-character DES encrypted passwords by standard guessing techniques . It is written to be flexible, configurable and fast, and to be able to make use of several networked hosts via the Berkeley rsh program (or similar), where possible.

Crack runs on UNIX only. It comes as a tarred, g'zipped file and is available at

To get Crack up and running, set the root directory. You assign this variable (Crack_Home) in the configuration files. The Crack_Home variable tells the Crack program where Crack's resources reside. To set this variable, edit the shell script Crack. After you do that, you can begin.


Most distributions of Crack are accompanied by a sample wordlist. However, that wordlist is limited. If you anticipate cracking large password files (or files in other languages), you will probably need additional dictionary files.


You begin your Crack session by starting the program and providing the name of the file to crack (as well as any command-line arguments, including specifications for using multiple workstations). A bare command line looks like this:

Crack my_password_file

What follows is difficult to describe, so I ran a sample Crack session. Crack started the process and wrote the progress of the operation to files with an out prefix. In this case, the file was called outSamsHack300. The following is an excerpt from that file:

001 1: pwc: Jan 30 19:26:49 Crack v4.1f: The Password Cracker,
002  (c) Alec D.E. Muffett, 1992
003 2: pwc: Jan 30 19:26:49 Loading Data, host=SamsHack pid=300
004 3: pwc: Jan 30 19:26:49 Loaded 2 password entries with 2 different
005  (salts: 100%
006 4: pwc: Jan 30 19:26:49 Loaded 240 rules from 'Scripts/dicts.rules'.
007 5: pwc: Jan 30 19:26:49 Loaded 74 rules from 'Scripts/gecos.rules'.
008 6: pwc: Jan 30 19:26:49 Starting pass 1 - password information
009 7: pwc: Jan 30 19:26:49 FeedBack: 0 users done, 2 users left to crack.
010 8: pwc: Jan 30 19:26:49 Starting pass 2 - dictionary words
011 9: pwc: Jan 30 19:26:49 Applying rule '!?Al'to file 'Dicts/bigdict'
012 10: pwc: Jan 30 19:26:50 Rejected 12492 words on loading, 89160 words
013  (left to sort
014 11: pwc: Jan 30 19:26:51 Sort discarded 947 words; FINAL DICTIONARY
015  (SIZE: 88213
016 12: pwc: Jan 30 19:27:41 Guessed ROOT PASSWORD root (/bin/bash
017  (in my_password_file) [laura] EYFu7c842Bcus
018 13: pwc: Jan 30 19:27:41 Closing feedback file.

Crack guessed the correct password for root in just under a minute. Line 1 reveals the time at which the process was initiated (Jan 30 19:26:49); line 12 reveals that the password Laura was cracked at 19:27:41. This session occurred on a 133MHz processor and 32MB of RAM.

Because the password file I used was small, neither time nor resources were an issue. In practice, however, if you crack a file with hundreds of entries, Crack will eat resources voraciously. This hunger is especially evident if you use multiple wordlists that are in compressed form. (Crack automatically identifies them as compressed files and decompresses them.)

As mentioned earlier, you can get around this resource drain. Crack can distribute the work to different workstations of different architectures. You can use Crack on an IBM compatible running Linux, a RS/6000 running AIX, and a Macintosh running A/UX.

Crack is extremely lightweight and one of the best password crackers available.


To perform a networked cracking session, you must build a network.conf file. This file identifies which hosts to include, their architecture, and several other key variables. You can also specify what command-line options are invoked as Crack is unleashed on each machine. In other words, each member machine can run Crack with different command-line options.


John the Ripper by Solar Designer

John was discussed in the NT section so I will only briefly touch on it here. Although John can crack both NT- and UNIX-based passwords, the one thing that is unique about John on the UNIX side of the fence is its capability to do raw brute-forcing. Performing a raw brute-force attack (trying every possible combination of characters) was impractical on hardware of a few years ago, but is a reality today. If you want to get medieval on a UNIX password file, John is the tool for you.

CrackerJack by Jackal

CrackerJack runs on the DOS platform but cracks UNIX passwords. Contrary to popular notions, CrackerJack is not a straight port of Crack. Nevertheless, CrackerJack is extremely fast and easy to use. For several years, CrackerJack has been the choice for DOS users.

Later versions were compiled using GNU C and C++. CrackerJack's author reports that, through this recompiling process, the program gained noticeable speed.

Some noticeable drawbacks to CrackerJack include

        You can only use one dictionary file at a time.

        Memory-allocation conventions prevent CrackerJack from running in Windows 95.

Despite these snags, CrackerJack is reliable and requires only limited resources. It takes sparse processor power, doesn't require a windowed environment, and can even run from a floppy.

CrackerJack is widely available. Here are a few reliable sites:

PaceCrack95 (

PaceCrack95 runs on Windows 95 in console mode or in a shell window. Its author reports that the development of PaceCrack95 was prompted by deficiencies in other DOS-based crackers. He writes

Well you might be wondering why I have written a program like this when there already is[sic] many out there that do the same thing. There are many reasons, I wanted to challenge myself and this was a useful way to do it. Also there was this guy (Borris) that kept bugging me to make this for him because Cracker Jack (By Jackal) doesn't run in Win95/NT because of the weird way it uses the memory. What was needed was a program that runs in Win95 and the speed of the cracking was up there with Cracker Jack.

To the author's credit, he created a program that does just that. It is fast, compact, and efficient.

You can find PaceCrack95 at

Star Cracker by the Sorcerer

Star Cracker, which was designed to work under the DOS4GW environment, is a complete password-cracking suite. Some of its more interesting advantages are

        A fail-safe power outage provision. If a blackout in your city shuts down your computer, your work is not lost. Upon reboot, Star Cracker recovers all work previously done (up until the point of the power outage) and keeps right on going.

        Time-release operation. You can establish time windows when the program does its work. That means you could specify, "Crack this file for 11 hours. When the 11 hours is up, wait 3 hours more. After the 3 hours, start again."

Star Cracker really makes the password-cracking process painless.

You can find Star Cracker at

Merlin by Computer Incident Advisory Capability (CIAC) DOE

Merlin is not a password cracker. Rather, it is a tool for managing password crackers as well as scanners, audit tools, and other security-related utilities. In short, it is a fairly sophisticated tool for holistic management of the security process.

Merlin works on UNIX platforms only. It has reportedly been tested (with positive results) on a number of flavors, including but not limited to IRIX, Linux, SunOS, Solaris, and HP-UX.

One of the main attractions of Merlin is that, although it was specifically designed to support only five common security tools, it is highly extensible. (It is written in Perl almost exclusively.) You could conceivably incorporate any number of tools into the scheme of the program.

Merlin is a wonderful tool for integrating a handful of command-line tools into a single, easily managed package. It addresses the fact that the majority of UNIX-based security programs are based in the command-line interface. The five applications supported are





        SPI (available to government contractors and agencies only)

Note that Merlin does not supply any of these utilities in the distribution. You must acquire these programs and then configure Merlin to work with them (similarly to the way one configures external viewers and helpers in Netscape's Navigator). The concept might seem lame, but the tool provides an easy, centralized point from which you can perform some fairly common (and grueling) security tasks. In other words, Merlin is more than a bogus front-end. In my opinion, it is a good contribution to the security trade.


Those programmers new to the UNIX platform might have to do a little hacking to get Merlin working. For example, Merlin relies on you to have correctly configured your browser to properly handle *.pl files. (It goes without saying that Perl is one requisite.) Also, Merlin apparently runs an internal HTTP server and looks for connections from the local host. This means you must have your system properly configured for loopback.


Merlin (and programs like it) represents an important and growing trend (a trend kicked off by Farmer and Venema). Because such programs are designed primarily in an HTML/Perl base, they are highly portable to various platforms in the UNIX community. They also tend to consume few network resources, and after the code is loaded into the interpreter, they move pretty fast. Finally, the tools are easier to use, making security less of an insurmountable task. The data is right there and easily manipulated. This trend can only help strengthen security and provide newbies with an education.

You can find Merlin at


Section: Chapter 14.  Password Crackers

Cracking Cisco, Application, and Other Password Types

Although you can certainly use password crackers for devious activities, there are plenty of legitimate reasons for needing to access data that might be password protected. For example, if an employee forgets the password to a protected-access database, or if someone leaves the company without passing on the pass phrase for a zip file, an organization might have legitimate needs to get at that data.

The following section goes over some of the password crackers for less common (not OS related) applications. I encourage the reader to note the diverse assortment of password crackers listed. Hopefully this list will help dispel the myth that application-level passwords are inherently secure. The truth of the matter is that rarely do application vendors create secure password-protection mechanisms most are easily broken.

Cracking Cisco IOS Passwords

Cisco stores encrypted login, username, and "enable" passwords in standard IOS configuration files. If these configuration files are not protected, they can be run through decryption scripts that will reveal the passwords in clear text. We will talk more about securing Cisco equipment in Chapter 22, "Cisco Routers and Switches," but, for now, know that protecting your configuration files is extremely important.

Many scripts exist for decrypting standard Cisco passwords. One such script can be found at

A neat tool for auditing Cisco router configuration files can be found at Cisco administrators would be wise to check this one out.

Commercial Application Password Crackers

There are a number of companies that provide commercial password cracking services and tools. Three of the fairly well known ones are

        PWD Service, Inc.

        Password Crackers, Inc.

        Sumin & Co.

Here is just a sample list of some of the applications these organizations offer password- cracking software for:

        Microsoft Word

        Microsoft Excel

        Microsoft Access

        Microsoft Outlook

        Microsoft Project

        Microsoft Backup

        Microsoft Money

        Lotus 1-2-3

        Lotus Word Pro






        Peachtree Accounting



It's important to note that many of these password crackers do their cracking in less then a few seconds. Although I am not a password or cryptography expert, I think it's safe to draw the conclusion that most application-based password protection schemes are little more then an annoyance for intruders. If you can crack them with a $30 piece of software in a few seconds, realize that anyone else can, too.

ZipCrack by Michael A. Quinlan

ZipCrack does just what you think it would: It is designed to brute-force crack passwords that have been applied to files with a *.zip extension. (In other words, it cracks the password on files generated with PKZIP.)

No documentation is included in the distribution (at least, not the few files that I have examined), but I am not sure there is any need for documentation. The program is straightforward. You simply provide the target file, and the program does the rest.

The program was written in Turbo Pascal, and the source code is included with the distribution. ZipCrack works on any IBM compatible that is a 286 or higher. The file description reports that ZipCrack cracks all the passwords generated by PKZIP 2.0. The author also warns that, although you can crack short passwords within a reasonable length of time, long passwords can take "centuries." Nevertheless, I sincerely doubt that many individuals provide passwords longer than five characters. ZipCrack is a useful utility for the average toolbox. It's one of those utilities you think you will never need, and later, at 3:00 in the morning, you swear bitterly because you don't have it.

Zipcrack can be found at

Glide (Author Unknown)

Glide does not provide a lot of documentation. This program is used exclusively to crack PWL files, which are password files generated in Microsoft Windows for Workgroups and Windows 95. The lack of documentation, I think, is forgivable because the C source is included with the distribution. The utility will only work, however, for PWL files created by early releases of Windows 95. Microsoft changed the PWL format in such a way that releases of 95 from OSR2 onward can no longer be cracked by Glide.

Glide can be found at

AMI Decode (Author Unknown)

AMI Decode is designed expressly to grab the CMOS password from any machine using an American Megatrends BIOS. Before you search for this utility, however, you might use the factory default CMOS password. It is, oddly enough, AMI. In any event, the program works, and that is what counts.

AMI Decode can be found at

PGPCrack by Mark Miller

Before readers who use PGP get all worked up about PGPCrack, a bit of background information is in order. Pretty Good Privacy (PGP) is probably the strongest and most reliable encryption utility available to the public sector. Its author, Phil Zimmermann, summed it up as follows:

PGP uses public-key encryption to protect email and data files. Communicate securely with people you've never met, with no secure channels needed for prior exchange of keys. PGP is well featured and fast, with sophisticated key management, digital signatures, data compression, and good ergonomic design.

PGP can apply a series of encryption techniques. One of these, which is discussed in Chapter 15, "Sniffers," is IDEA. To hint about how difficult IDEA is to crack, here is an excerpt from the PGP Attack FAQ, authored by Route (an authority on encryption and the editor of Phrack magazine):

If you had 1,000,000,000 machines that could try 1,000,000,000 keys/sec, it would still take all these machines longer than the universe as we know it has existed and then some, to find the key. IDEA, as far as present technology is concerned, is not vulnerable to brute-force attack, pure and simple.

In essence, a message encrypted using a 1,024-bit key generated with a healthy and long passphrase is, for all purposes, unbreakable. Why did Mr. Miller author this interesting tool? Passphrases can be poorly chosen, and if you are going to crack a PGP-encrypted message, the passphrase is a good place to start. Miller reports

On a 486/66DX, I found that it takes about 7 seconds to read in a 1.2 megabyte passphrase file and try to decrypt the file using every passphrase. Considering the fact that the NSA, other government agencies, and large corporations have an incredible amount of computing power, the benefit of using a large, random passphrase is quite obvious.

Is this utility of any use? It is quite promising. Miller includes the source with the distribution as well as a file of possible passphrases. (I have found that at least one of those passphrases is one I have used.) The program is written in C and runs in DOS, UNIX, and OS/2 environments.

You can find PGPCrack at


Section: Chapter 14.  Password Crackers

Other Resources

This section contains a list of sources for further education. Some of these documents are not available on the Internet. However, you can obtain some articles through various online services (perhaps Uncover) or at your local library through interlibrary loan or microfiche. You might have to search more aggressively for some of these papers, perhaps using the Library of Congress ( or perhaps an even more effective tool, such as WorldCat (


Many of the files for papers have .ps extensions. This signifies a PostScript file. PostScript is a language and method of preparing documents. It was created by Adobe, the makers of Acrobat and Photoshop.

To read a PostScript file, you need a viewer. One good viewer is Ghostscript, which is shareware at

Another good package (and a little more lightweight) is a utility called Rops. Rops is available for Windows and is located at (the ZDNet software library) (the Oak software repository)


Internet Resources

Observing Reusable Password Choices. Purdue Technical Report CSD-TR 92-049, Eugene H. Spafford, Department of Computer Sciences, Purdue University, July 3, 1992. Search string:

Password Security: A Case History. Robert Morris and Ken Thompson, Bell Laboratories. Date: Unknown. Search string:

Opus: Preventing Weak Password Choices. Purdue Technical Report CSD-TR 92-028, Eugene H. Spafford, Department of Computer Sciences, Purdue University, June 1991. Search string: opus.PS.gz

Federal Information Processing Standards Publication 181. Announcing the Standard for Automated Password Generator. October 5, 1993.

Augmented Encrypted Key Exchange: A Password-Based Protocol Secure Against Dictionary Attacks and Password File Compromise. Steven M. Bellovin and Michael Merrit, AT&T Bell Laboratories. Date: Unknown. Search string:

A High-Speed Software Implementation of DES. David C. Feldmeier, Computer Communication Research Group, Bellcore, June 1989. Search string:

Using Content Addressable Search Engines to Encrypt and Break DES. Peter C. Wayner, Computer Science Department, Cornell University. Date: Unknown. Search string:

Encrypted Key Exchange: Password-Based Protocols Secure Against Dictionary Attacks. Steven M. Bellovin and Michael Merrit, AT&T Bell Laboratories. Date: Unknown. Search string:

Computer Break-Ins: A Case Study. Leendert Van Doorn, Vrije Universiteit, The Netherlands, January 21, 1993. Search string:

Security Breaches: Five Recent Incidents at Columbia University. Fuat Baran, Howard Kaye, and Margarita Suarez, Center for Computing Activities, Colombia University, June 27, 1990. Search string:

Optimal Authentication Protocols Resistant to Password Guessing Attacks. Li Gong, Stanford Research Institute, Computer Science Laboratory, Men Park, CA. Date: Unknown. Search string: optimal-pass.dvi or

Publications and Reports

Undetectable Online Password Guessing Attacks. Yun Ding and Patrick Horster, OSR, 29(4), pp. 77 86. October 1995.

A Password Authentication Scheme Based on Discrete Logarithms. Tzong Chen Wu and Chin Chen Chang, International Journal of Computational Mathematics; Vol. 41, Number 1--2, pp. 31 37. 1991.

Differential Cryptanalysis of DES-Like Cryptosystems. Eli Biham and Adi Shamir, Journal of Cryptology,Vol. 4(1). pp. 3 72. 1990.

A Proposed Mode for Triple-DES Encryption. Don Coppersmith, Don B. Johnson, and Stephen M. Matyas. IBM Journal of Research and Development,40(2), pp. 253 262. March 1996.

An Experiment on DES Statistical Cryptanalysis. Serve Vaudenay, Conference on Computer and Communications Security, pp. 139 147. ACM Press. March 1996

Department of Defense Password Management Guideline. If you want to gain a more historical perspective regarding password security, start with the Department of Defense Password Management Guideline. This document was produced by the Department of Defense Computer Security Center at Fort Meade, Maryland.

You can find the Department of Defense Password Management Guideline at


Section: Chapter 14.  Password Crackers


Password crackers provide a valuable service to system administrators by alerting them of weak passwords on the network. The problem is not that password crackers exist; the problem is that they aren't used frequently enough by the good guys. Administrators should take the time to build password cracking into their monthly routines. By doing so, they can proactively pursue any weaknesses in their enterprise that result from weak passwords. However, administrators should also take care to ensure that both the raw password files and the results of their cracking efforts be deleted after their cracking sessions. Leftover password files can create issues that are worse then bad passwords themselves.

Finally, although the days of passwords serving as a primary means of authentication might be numbered, their overall use is not. Pass phrases will be used for some time to come for protecting keys, certificates, and a varying assortment of protected data. The technology might become more complex, but the solution to the surrounding problems will not. Education is key use it.


Enterprises - Maximum Security
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