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Password Attacks

Passwords are the most commonly used computer security tool in the world today. In many organizations, the lowly password often protects some of the most sensitive secrets imaginable, including health care information, confidential business strategies, sensitive financial data, and so on. Unfortunately, with this central role in security, easily guessed passwords are often the weakest link in the security of our systems. By simply guessing hundreds or thousands of passwords, an attacker could gain access to very sensitive information or shut down critical computing systems.

Compounding this problem with passwords is the fact that every user has at least one password, and many users have dozens of passwords. Users are forced to remember and maintain passwords for logging into the network, signing on to numerous applications, accessing frequently used external Web sites, logging into voice mail, and even making long-distance phone calls with a calling card. On almost all systems, the users themselves choose the passwords, placing the burden of security on end users who either do not know or sometimes do not care about sound security practices. Users often choose passwords that are easy to remember, but are also very easily guessed. We frequently encounter passwords that are set to days of the week, the word password, or simple dictionary terms. A single weak password for one user on one account could give an attacker a foothold on a system. Most users manually synchronize their passwords for every password-protected system they access. Sadly, therefore, a user who has a password in your high-security environment might be using the same password for that external e-commerce application over which your organization has no control. After guessing one weak password in the low-security environment, the attacker can take over an account on the supposedly higher security system. Indeed, the plague of passwords is quite widespread.

Why, then, do we continue to rely on them so much? We do so because password-authentication mechanisms are really cheap. Most operating systems and applications have built-in password authentication, so their users and administrators have simply applied the least expensive (and often least secure) tool in place.

For even a low-skill attacker, guessing such passwords and gaining access can be quite trivial. Numerous freely available tools automatically guess passwords at relatively high speeds, looking for a weak password to enter a system. Let's explore how these password-guessing tools work.

Guessing Default Passwords

Many applications and operating systems include built-in default passwords established by the vendor. Often, overworked, uninformed, or lazy administrators fail to remove default passwords from systems. Attackers can quickly and easily guess these default passwords to gain access to the target. The Phenoelit hacking group out of Germany maintains a huge database of default passwords for a variety of platforms, available at www.phenoelit.de/dpl/dpl.html. This Web site, shown in Figure 7.15, includes default passwords for systems ranging from 3COM switches to Zyxel's modem routers, and everything in between.

Figure 7.15

Figure 7.15 An online database of default passwords.

Password Guessing Through Login Attacks

What if none of the default passwords works? Another technique for guessing weak passwords is to run a tool that repeatedly tries to log in to the target system across the network, guessing password after password. The attacker configures a password-guessing tool with a common or known user ID on the target system. The password-guessing tool then guesses a password, perhaps using a wordlist from a dictionary. The attacker points the tool at the target machine, which might have a command-line login prompt, Web front-end login dialog box, or other method of requesting a password. The attacker's tool transmits its user ID and password guess to the target, trying to log in, and then automatically determines if the guess was successful. If not, another guess is tried. Guess after guess is launched until the tool discovers a valid password.

One of the most fully functional and easy-to-use tools for automating this password-guessing attack is Brutus, available for free at www.hoobie.net/brutus. It runs on Windows, has a point-and-click GUI, shown in Figure 7.16, and is remarkably effective.

Figure 7.16

Figure 7.16 Brutus in action.

The attacker configures Brutus with the following information:

  • The target system address or domain name
  • The source of password guesses, which can be a file of words or a brute-force selection of all possible character combinations
  • The protocol to use when interacting with the target, which could be HTTP with Basic Authentication, HTTP with an HTML form, Post Office Protocol 3 (POP3) e-mail, FTP, Windows authentication and file sharing with Server Message Block (SMB) protocol, and Telnet
  • The text that Brutus will receive if authentication is successful
  • The text the application generates when authentication fails

Then, the attacker simply clicks the Start button. Brutus grinds away for between minutes and weeks, and starts popping back with answers.

It's important to note that Brutus often yields many false positives due to bugs in the code, not problems with this overall type of attack. Keep that in mind if you ever run Brutus: Not all of your discovered accounts will be accurate!

If you want a more UNIX/Linux-friendly password-guessing tool with better accuracy, you should check out THC Hydra, available for free at http://thc.org/thc-hydra. This fine tool, written by van Hauser, includes a command-line interface and a GUI option if you really want it. Hydra runs on Linux and many flavors of UNIX, and even works on Windows, provided that you've installed the free Cygwin environment, an amazing UNIX-like world that runs on top of Windows. You can get the Cygwin environment for free at www.cygwin.com.

The nicest part about Hydra is its generous protocol support. It can guess passwords for more than a dozen different application-level protocols, including Telnet, FTP, HTTP, HTTPS, HTTP-PROXY, LDAP, SMB, SMBNT, MS-SQL, MYSQL, REXEC, SOCKS5, VNC, POP3, IMAP, NNTP, PCNFS, ICQ, SAP/R3, Cisco auth, Cisco enable, and Cisco AAA. Whew! That's a lot of different applications, making it highly useful in password-guessing attacks. Also, Hydra doesn't suffer from the false positive problems of Brutus, making it my personal favorite for password guessing.

Password guessing can be a slow process. Each login attempt could take a few seconds. To go through an entire 40,000-word dictionary could take days, and guessing random combinations of characters could require weeks or months before a usable password is discovered. However, the greatest asset the attackers have is time. They can be very determined when focused on a given target, and often don't mind spending many months trying to gain access.

Beyond being time consuming, this password-guessing technique has additional limitations. The constant attempts to log in to the target generate a significant amount of regular network traffic and log activity, which could easily be noticed by a diligent system administrator or an IDS. An additional challenge an attacker faces when trying to guess a password is account lockout. Some systems are configured to disable a user account after a given number of incorrect login attempts with faulty passwords. The account is reenabled only by a user calling the help desk, or through an automated process after a period of time expires. Either way, the attacker's guessing can be detected or at least slowed down significantly. Account lockout features are a good idea in preventing password-guessing attacks. However, with account lockout in place, an attacker could conduct a DoS attack by purposely locking out all of your accounts using a script, so be careful to fine-tune your account lockout policies based on the threats you face.

The Art and Science of Password Cracking

Guessing default passwords usually doesn't work, because many administrators change the defaults. Password guessing with an automated tool could take a very long time, and, at its worst, it could get an attacker detected or lock out accounts. A much more sophisticated approach to determining passwords that avoids these problems is password cracking, an approach totally separate from password guessing. However, to analyze how password cracking works, you first need to understand how passwords are stored on most systems.

When you log in to most machines, whether they are Linux systems, Windows boxes, Novell servers, Cisco routers, or any other type of machines, you typically provide a user ID and password to authenticate. The system has to check whether your authentication information is accurate to make the decision whether to log you in or not. The computer could base this decision on the contents of a local file of the passwords for all users, comparing the password you just typed in with your password in the file. Unfortunately, a file with every user's password in clear text would be an incredible security liability, a sitting duck waiting for the bad guys to harvest it. An attacker gaining access to such a password file would be able to log in as any user of the system.

System designers, realizing this dilemma of requiring a list of passwords to compare to for user login without having a huge security hole, decided to solve the problem by applying cryptographic techniques to protect each password in the password file. Thus, for most systems, the password file contains a list of user IDs and representations of the passwords that are encrypted or hashed. I use the words encrypted or hashed, because a variety of different cryptographic algorithms are applied. Some systems use pure encryption algorithms, like the Data Encryption Standard (DES), which require a key for the encryption. Others use hash algorithms, such as Message Digest 4 (MD4), which are one-way functions that transform data with or without a key. Either way, the password is altered using the crypto algorithm so that an attacker cannot determine the password by directly looking at its encrypted or hashed value in the password file.

When a user wants to log in to the system, the machine gathers the password from the user, applies the same cryptographic transformation used to generate the password file, and compares the results. If the encrypted or hashed value of your password matches the encrypted or hashed value in the file, you are allowed to log in. Otherwise, you are denied access. The process works beautifully, allowing you to log in successfully, turning away attackers, and never keeping a clear text file of password.

Let's Crack Those Passwords!

  • Lather. Rinse thoroughly. Repeat. These are directions from a shampoo bottle, which, if followed literally, would leave you in the shower for eternity.

Most systems include a password file that contains encrypted or hashed representations of the passwords. Password cracking involves stealing the encrypted password representations and trying to recover the original clear text password using an automated tool. A password-cracking tool operates by setting up a simple loop, as shown in Figure 7.17.

Figure 7.17

Figure 7.17 Password cracking is really just a loop.

A password-cracking tool can form its password guesses in a variety of ways. Perhaps the simplest method is to just throw the dictionary at the problem, guessing one term after another from a dictionary. A large number of dictionaries are available online, in many languages, including English, Russian, Japanese, French, and, for you Star Trek fans, even Klingon! Most password-cracking tools come with a small but effective wordlist. For example, John the Ripper's list includes approximately 2,000 words, whereas the Cain wordlist includes a whopping 306,000 entries!

For other wordlists that are quite effective, check out two sources: the CERIAS wordlist collection (http://ftp.cerias.purdue.edu/pub/dict/dictionaries/), and the Moby wordlist (www.dcs.shef.ac.uk/research/ilash/Moby/). Both lists are free, and include hundreds of thousands of words from a variety of languages. Of course, if the target's passwords are not dictionary terms, this technique will fail. Happily for attackers, it almost always succeeds.

Beyond guessing dictionary terms, many password-cracking tools support brute-force cracking. For this type of attack, the tool guesses every possible combination of characters to determine the password. The tool might start with alphanumeric characters (a–z and 0–9), and then progress to special characters (!@#$, and so on). Even for a fast password-cracking tool, this brute-force guessing process can take an enormous amount of time, ranging from hours to centuries. It all depends on the strength of the password crypto algorithm and how difficult the user's password is to guess.

Hybrid password-cracking attacks are a nice compromise between quick but limited dictionary cracks and slow but effective brute-force cracks. In a hybrid attack, the password-cracking tool starts guessing passwords using a dictionary term. Then, it creates other guesses by appending or prepending characters to the dictionary term. By methodically adding characters to words in a brute-force fashion, these hybrid attacks are often extremely successful in determining a password. The best hybrid generators even start to shave characters off of dictionary terms in their guess-creating algorithms.

From an attacker's perspective, password cracking is fantastic, because the cracking loop does not have to run on the victim machine. If the attackers can steal the encrypted or hashed password file, they can run the password-cracking tool on their own systems, in the comfort of their own homes or on any other machine that suits their fancy. This makes password cracking much faster than password guessing through trying to log in to the target machine. Although using a password-guessing tool to log in across the network requires many valuable seconds to evaluate each guess, a password-cracking tool can guess thousands or tens of thousands of passwords per second! The password cracker only has to operate on the stolen password file stored locally, applying quick and optimized cryptographic algorithms. Every word in a 50,000-word dictionary can be attempted in only a few minutes.

Furthermore, the more CPU cycles the attackers throw at the problem, the more guesses they can make and the faster they can recover passwords. So an attacker who has taken over dozens of machines throughout the world and is looking to crack the passwords of a new victim can divide up the password-cracking task among all of these machines to set up a password-cracking virtual supercomputer. Or, if an attacker has compromised 100,000 machines using a bot for remote control of these victims, the attacker can harvest the processing power of a 100,000-node network to make the password cracking operation really fly! We discuss the nefarious bots that can support such a feat in more detail in Chapter 10, Phase 4: Maintaining Access.

Password-cracking tools have been around for a couple of decades, and an enormous number of them are available. Some of the most notable password-cracking tools in widespread use today include the following:

  • Cain, a fantastic free tool available from Massimiliano Montoro at www.oxid.it/cain.html
  • John the Ripper, a powerful free password cracker for UNIX/Linux and some Windows passwords, written by Solar Designer, available at www.openwall.com/john
  • Pandora, a tool for testing Novell Netware, including password cracking, written by Simple Nomad, and available at www.nmrc.org/project/pandora
  • LC5, the latest incarnation of the venerable L0phtCrack password cracker, an easy-to-use but rather expensive commercial password cracker at www.atstake.com/products/lc/purchase.html

To understand how these tools work in more detail, let's explore two of the most powerful password crackers available today, Cain and John the Ripper.

Cain and Abel: Cracking Windows (and Other) Passwords with a Beautiful GUI

Cain and Abel are a dynamic duo of security tools that can be used for either attacking systems or administering them. Their name is a nod to the biblical brothers who didn't get along all that well. The Cain and Abel tools, happily, work together far better than those ancient brothers ever did. Typically, a user relies on Cain to gather information about systems and to manipulate them directly, while Abel usually runs as a background process a user can access remotely to dump information about a target environment. In other words, Cain is highly interactive, with a fancy GUI offering all kinds of interesting attack functionality. Abel runs in the background, and can be remotely accessed to dump data from its host system.

Frankly, the Cain and Abel pair of tools is hard to categorize. This amazing software contraption, created by Massimiliano Montoro, includes more than a dozen different useful capabilities that we discuss throughout this book. Although we're covering Cain and Abel here in the section on password cracking, Cain and Abel are not designed just for cracking passwords. They are extremely feature rich, including just about everything and the kitchen sink, as a final touch! Montoro constantly scours the Internet for useful ideas included in white papers and other tools, and then adds such capabilities to Cain and Abel, making the duo a powerful collection of various computer attack widgets. Cain includes the following functionalities:

  • Automated WLAN discovery, in essence a war-driving tool that looks quite similar to NetStumbler, the tool we discussed in Chapter 6.
  • A GUI-based traceroute tool, using the same traceroute techniques we discussed in Chapter 6 in the context of the traceroute, tracert, and Cheops-ng tools.
  • A sniffer for capturing interesting packets from a LAN, including a variety of user IDs and passwords for several protocols. We discuss sniffers in more detail in Chapter 8.
  • A hash calculator, which takes input text and calculates its MD2, MD4, MD5, SHA-1, SHA-2, and RIPEMD-160 hashes, as well as the Microsoft LM, Windows NT, MySQL, and PIX password representation of that text. That way, an attacker can quickly verify assumptions associated with specific information discovered on a target system.
  • A network neighborhood exploration tool to scan for and find interesting Windows servers available on the network.
  • A tool to dump and reveal all encrypted or hashed passwords cached on the local machine, including the standard Windows LM and NT password representations, as well as the application-specific passwords for Microsoft Outlook, Outlook Express, Outlook Express Identities, Outlook 2002, Microsoft Internet Explorer, and MSN Explorer.
  • An ARP cache poisoning tool, which can be used to redirect traffic on a LAN so that an attacker can more easily sniff in a switched environment, a technique we discuss in more detail in Chapter 8.
  • A remote promiscuous mode checker, to try to test whether a given target machine is running a sniffer that places the network interface in promiscuous mode.
  • Numerous other features, with new functionality added on a fairly regular basis.

Cain integrates each of these functions into a nice GUI, which, although complex, sorts out the individual features quite nicely. The Abel tool, on the other hand, has no GUI. Instead, it runs as a service in the background, giving remote access capabilities to a lot of functionality, including the following:

  • A remote command shell, rather like the backdoor command shells we discuss in Chapter 10.
  • A remote route table manager, so an administrator can tweak the packet routing rules on a Windows machine.
  • A remote TCP/UDP port viewer that lists local ports listening on the system running Abel, rather like the Active Ports and TCPView tools we discussed in Chapter 6.
  • A remote Windows password hash dumper, which an attacker can use to retrieve the encrypted and hashed Windows password representations from the Security Accounts Manager (SAM) database, suitable for cracking by ... you guessed it ... the Cain tool.

In this section, however, we're going to focus on one of the most useful capabilities of Cain, namely its extremely functional password cracker. Cain is able to crack passwords for more than a dozen different operating system and protocol types. Just for the Windows operating system, Cain can crack the following password representations:

  • Microsoft LM, the really weak Windows password authentication also known as LanMan, still included by default in all Windows NT, 2000, XP, and 2003 systems in the local SAM database
  • The LM challenge passed across the network, which is a challenge–response authentication protocol based on the underlying LM hash, but includes special features for network authentication to a Windows domain or a file server
  • Windows NT hash, a form of Windows password storage stronger than LM, supported in Windows NT, 2000, XP, and 2003 machines and stored in the local SAM database, as we discussed in Chapter 4, Windows NT/2000/XP/2003 Overview.
  • NTLMv1, a challenge–response protocol passed across the network, offering slightly better security than the LM challenge passed across the network
  • NTLMv2, an even stronger form of challenge–response authentication across a Windows network
  • MS-Kerberos5 Pre-Auth, the Microsoft Kerberos authentication deployed in some Windows environments
Retrieving the Password Representations from Windows

To use Cain to crack Windows operating system passwords, the attacker usually first grabs a copy of the password representations stored in the SAM database of the target machine. To accomplish this, Cain includes a built-in feature to dump password representations from the local system or any other machine on the network. However, this built-in password dump capability requires administrator privileges on the system with the target SAM database. These administrator rights are required because the password dump function must attach to the running Windows authentication processes to extract the SAM database right from their memory space, a process that requires administrative privileges. It's interesting to note that dumping the SAM database from memory allows Cain to bypass Windows Syskey protection, which adds an extra 128 bits of cryptographic protection around the SAM database while it resides on the hard drive only. When in the memory of running authentication processes, Cain can easily grab it with administrative rights. Besides Cain, an alternative program for getting these password representations using the same memory-dumping technique is the free Pwdump3 program, available at www.openwall.com/passwords/nt.shtml. As with Cain, to use Pwdump3 to extract password representations, the attacker must have administrative privileges on the target system.

Besides dumping the SAM, attackers also have many other options for getting a copy of the password representations. They could search the system looking for files used during a system backup and steal the password representations. For example, when an administrator backs up a system using the built-in Windows tool Ntbackup.exe, by default, a copy of the SAM database with the password representations is usually placed in the %systemroot%\repair\sam._ file.

Another option for getting the password representations is to steal the administrator recovery floppy disks. When a Windows system is built, a good administrative practice is to create floppy disks that can be used to recover the machine more quickly if the operating system gets corrupted. These floppy disks include a copy of the SAM database with at least a representation of the administrator's password. Alternatively, an attacker with physical access to the target machine could simply boot the system from a Linux CD-ROM and retrieve the SAM database by dumping it from the local registry image on the hard drive. A handy tool for retrieving and altering Windows passwords using a Linux boot disk can be found at http://home.eunet.no/~pnordahl/ntpasswd/bootdisk.html. This tool can be used to change the administrator or other user's password, even if Syskey is installed. It's important to note, however, that changing a user's password by booting to a Linux CD-ROM causes the system to lose access to the EFS keys for that user on Windows XP and 2003. Thus, on those versions of Windows, if you use the password-changing boot disk, you'll lose all EFS-protected data in the accounts for which you change passwords. On Windows 2000, the EFS keys are stored differently, letting this Linux boot disk change the passwords without losing EFS-encrypted files.

Cain offers one final option for getting password representations: sniffing them off of the network. Cain includes a very powerful integrated network capture tool that monitors the LAN looking for Windows challenge–response authentication packets, which Windows will send in a variety of different formats, depending on its configuration, including LM Challenge–Response, NTLMv1, NTLMv2, and Microsoft Kerberos. Whenever users try to authenticate to a domain or mount a remote file share or print server, their Windows machine authenticates to the server using one of these protocols. Taken together, the challenge and response associated with each protocol are based cryptographically on the user's password. After grabbing the challenge and response from the network using its integrated sniffing tool, Cain can crack them to determine the user's password. We discuss sniffers and how they manipulate LAN traffic in more detail in Chapter 8. But for now, keep in mind that Cain can sniff a variety of Windows authentication protocols and crack the passwords associated with them.

Configuring Cain

Cain is very easy to configure, as shown in Figure 7.18. The attacker can set up the tool to do dictionary attacks (using any wordlist of the attacker's choosing as a dictionary, or the integrated 306,000-word dictionary Cain includes). Cain also supports hybrid attacks that reverse dictionary guesses, apply mixed case to guesses, and even append the numbers 00 through 99 to dictionary words. It also offers complete brute-force password-cracking attacks, attempting all possible character combinations to form password guesses.

Figure 7.18

Figure 7.18 Configuration options for Cain.

Finally, instead of forming, encrypting, and comparing the password guesses in real time, Cain supports a password-cracking concept sometimes called Rainbow tables, in honor of the first tool that implemented this attack, RainbowCrack, by Zhu Shuanglei. With a Rainbow-like attack, the bad guy computes an encrypted dictionary in advance, storing each password along with its encrypted form in memory or in a file on the hard drive. This table is typically indexed for fast searching based on the encrypted password representation. Then, when mounting a password-cracking attack, the bad guy bypasses the guess–encrypt–compare cycle, instead just grabbing the cryptographic password representation from the victim machine and looking it up in the Rainbow table. After spending the initial time and energy to create the Rainbow tables, all subsequent cracking is much quicker, because the tool simply has to look up the password representations in the table. In effect, we preload most of the password-cracking work. For Cain, the attacker can generate the Rainbow tables using a separate tool called Winrtgen.exe, available at the Cain Web site (www.oxid.it). Then, once the encrypted wordlist is developed, the attacker can point Cain to it to perform the comparisons to determine the passwords.

Cracking Passwords with Cain

After loading the password representations, selecting a dictionary, and configuring the options, the attacker can run Cain by clicking the Start button. Cain generates and tests guesses for passwords very quickly. Table 7.1 depicts the amount of time necessary to crack the very weak LM hashes using a quad-processor 2.4-GHz machine, a pricy machine, but not out of range for some attackers. Of course, with Moore's law resulting in faster computers every other year, these numbers are plummeting. Keep in mind, however, that Table 7.1 illustrates the times for LM hash cracking. NT hashes are several orders of magnitude stronger than the incredibly weak LM hashes, for reasons described in Chapter 4.

Table 7.1. Approximate LM Cracking Times with Cain, Using a Quad-Processor Machine

Character Set



< 2 hours

Alphanumeric, some special characters

< 10 hours

Alphanumeric, all special characters (except high-end ASCII typed with the ALT key)

< 120 hours (5 days!)

That's pretty impressive performance! A full brute-force attack (every possible keystroke character) against the weak LM representations takes less than 120 hours, or 5 days, to recover any password, regardless of its value of normal alphanumeric and special characters (those that you can form using the SHIFT key). And, if the attacker has more processing horsepower, the attack requires even less time. It's important to note, though, that Windows allows users to choose passwords that include the upper-end ASCII characters by holding down the ALT key and typing numbers to represent such characters. Although these ALT characters significantly drive up password cracking times, most users don't rely on them, instead favoring the easier-to-type alphanumeric and special characters.

The main Cain screen, illustrated in Figure 7.19, shows the information dumped from the target's SAM database (including User Name, LM representation, and NT Hash). As Cain runs, each successfully cracked password is highlighted in the display. There is one especially interesting column in Figure 7.19: the "<8" notation. This column is checked for each password with an LM representation that ends in AAD3B43... That's because, as we discussed in Chapter 4, the original password was seven characters or less, padded to be exactly 14 characters by the LM algorithm. When LM splits the resulting string into two seven-character pieces, the high end will always be entirely padding. Encrypted padding, with no salts, always has the same value, AAD3B43 and so on. Salts, those little random numbers used to boost the difficulty of cracking passwords, are described in more detail in Chapter 4. Of course, if Windows used salts to force some nonpredictability into the password crypto scheme, the same encrypted padding would indeed have different results. So, the presence of this "<8" column illustrates two things: that the passwords are split into two seven-character pieces by LM, and that no salts are used in Windows.

Figure 7.19

Figure 7.19 Successful crack using Cain.

Using Cain's Integrated Sniffer

As we discussed earlier, Cain allows an attacker to sniff challenge–response information off of the network for cracking. But how can an attacker force users to send this information across the network? Well, attackers could position their machine or take over a system on the network at a point where they will see all traffic for users authenticating to the domain or a very popular file server. In such a strategic position, whenever anyone authenticates to the domain or tries to access a share, the attacker can run Cain in sniffing mode to snag user authentication information from the network.

Of course, it might be very difficult for attackers to insert themselves in such a sensitive location. To get around this difficulty, an attacker can trick a user via e-mail into revealing his or her password hashes. Consider the e-mail shown in Figure 7.20, which was sent by an attacker, pretending to be the boss. Note that the message includes a link to a file share on the machine SOMESERVER, in the form of file://SOMESERVER. On this SOMESERVER machine, the attacker has installed Cain and is running the integrated sniffing tool.

Figure 7.20

Figure 7.20 Would you trust this e-mail?

When the victim clicks the file:\\ link, the victim's machine attempts to mount the share on the attacker's server, interacting with the server using a Windows challenge–response protocol such as LM Challenge, NTLMv1, NTLMv2, or Kerberos, depending on the system's configuration. Once the victim clicks the link, the attacker's sniffer displays the gathered challenge and response, as shown in Figure 7.21.

Figure 7.21

Figure 7.21 Cain's integrated sniffer captures the challenge–response from the network for cracking.

To complete the attack, the attacker can save this captured data and feed it into Cain to retrieve the user's password, as shown in Figure 7.22. This technique, which combines social engineering via e-mail, sniffing data from the network, and password cracking, really demonstrates the power of several aspects of Cain.

Figure 7.22

Figure 7.22 A sniffed Windows challenge–response successfully cracked.

Cain Doesn't Do Just Windows

Beyond these Windows operating system password-cracking capabilities, Cain can also crack Cisco-IOS Type-5 enable passwords, Cisco PIX enable passwords, APOP-MD5 hashes, CRAM-MD5 hashes, RIPv2-MD5 hashes, OSPF-MD5 hashes, VRRP-HMAC-96 hashes, VNC's 3DES passwords, RADIUS Shared Secrets, Password List (PWL) files from Windows 95 and Windows 98, Microsoft SQL Server 2000 passwords, MySQL323 passwords, MySQLSHA1 hashes, and even IKE preshared keys. Whew! That's quite an exhaustive list. That last item in the list, associated with the IKE protocol, is especially useful for the bad guys in a VPN environment. Many IPSec implementations use IKE to exchange and update their crypto keys. Most systems and VPN gateways, by default, use IKE in a manner called aggressive mode, designed to exchange new keys quickly across the network. Many organizations have deployed their IPSec products using a preshared key as an initial secret to exchange the first set of session keys via aggressive mode IKE. This preshared key is usually just a password typed by an administrator into the IPSec clients and VPN gateway. Unfortunately, if an attacker sniffs the aggressive mode IKE exchange using Cain's built-in sniffer, the bad guy can crack this preshared key. Using this information, the attacker can then load the preshared key into the attacker's own IPSec client, and ride in through the VPN gateway, impersonating the original user. This preshared key IKE cracking capability originated in a tool called IKE Crack, but the functionality has been nicely imported into both Cain's sniffer and password-cracking features.

Cracking UNIX (and Other) Passwords Using John the Ripper

Despite its ability to attack other operating systems, Cain still runs just on Windows. Another free, high-quality password cracker that can run on more environments is John the Ripper, one of the best tools today focused only on password cracking. John the Ripper (called John for short) is a free tool developed by Solar Designer, the gentleman we discussed earlier in this chapter who wrote the nonexecutable kernel patch for Linux to defend against stack-based buffer overflows. Although John is focused on cracking UNIX and Linux passwords, it has some extended modules that can crack other password types, including Windows LM representations and NT hashes.

John runs on a huge variety of platforms, including Linux, UNIX, Windows of all kinds, and even the ancient DOS platform. Yes, you can dust off that old DOS system and use it to crack passwords. To boost its speed, John even includes optimized code to take advantage of various specific CPU capabilities, such as Intel's MMX technology.

Further showing its great flexibility, John can be used to crack passwords from a variety of UNIX variants, including Linux, FreeBSD, OpenBSD, Solaris, Digital UNIX, AIX, HP-UX, and IRIX. Although it was designed to crack UNIX passwords, John can also attack LM hashes from Windows machines. Also, Dug Song, the author of the FragRouter IDS and IPS evasion tool that we discussed in Chapter 6, has written modular extensions for John that crack files associated with the S/Key one-time-password system and AFS/Kerberos Ticket Granting Tickets, which are used for cryptographic authentication. Finally, a developer named Olle Segerdahl has written an NT hash-cracking module for John, freely available at www.openwall.com//john/contrib/john-ntlm-v03.diff.gz.

Retrieving the Encrypted Passwords

As described in Chapter 3, Linux and UNIX Overview, UNIX systems store password information in the /etc directory. Older UNIX systems store encrypted passwords in the /etc/passwd file, which can be read by any user with an account on the system. For these types of machines, an attacker can grab the encrypted passwords very easily, just by copying /etc/passwd.

Most modern UNIX variants include an option for using shadow passwords. In such systems, the /etc/passwd file still contains general user account information, but all encrypted passwords are moved into another file, usually named /etc/shadow or /etc/secure. Figures 7.23 and 7.24 show the /etc/passwd and /etc/shadow files, respectively, from a system configured to use shadow passwords. A shadow password file (/etc/shadow or /etc/secure) is only readable by users with root-level privileges. To grab a copy of a shadow password file, an attacker must find a root-level exploit, such as a buffer overflow of program that runs as root or a related technique, to gain root access. After achieving root-level access, the attacker makes a copy of the shadow password file to crack.

Figure 7.23

Figure 7.23 When password shadowing is used on a system, the /etc/passwd file contains user information, but no passwords.

Figure 7.24

Figure 7.24 The corresponding /etc/passwd file contains the encrypted passwords.

Another popular technique used on systems with or without shadow passwords involves causing a process that reads the encrypted password file to crash, generating a core dump file. On UNIX machines, the operating system will often write a core file containing a memory dump of a dying process that might have been a victim of a buffer overflow that simply crashed the target process. The core file is generated for debugging purposes and to store unsaved data. After retrieving a copy of a core file from a process that read the encrypted passwords before it died, an attacker can comb through it to look for the encrypted passwords. This technique of mining core dumps is particularly popular in attacking FTP servers. If attackers can crash one instance of the FTP server, causing it to create a core dump, they can then use another instance of the FTP server to transfer the core file from the target machine. They'll then pore through the core file looking for passwords to crack to gain access to the FTP server.

Configuring John the Ripper

Although it doesn't have a fancy GUI like Cain, the command-line John tool is still trivially easy to configure. The attacker must feed John a file that includes all user account and password information. On a UNIX system without shadow passwords, all of this information is available in the /etc/passwd file itself, so that's all John requires. On a system with shadow passwords, this information is stored in /etc/passwd and /etc/shadow (or /etc/secure). To merge these two files into a single file for input, John includes a program called, suitably enough, unshadow, which is shown in Figure 7.25.

Figure 7.25

Figure 7.25 Running the unshadow script from John the Ripper.

Another very nice feature of John is its ability to detect automatically the particular encryption algorithm to use during a cracking exercise, differentiating various UNIX and Linux password encryption techniques from each other, as well as the Windows LM representation. This autodetect capability is based on the character set, length, and format of the given file containing the passwords. In this way, John practically configures itself automatically. Although the autodetect function is nifty, the absolute greatest strength of John is its ability to create many permutations quickly for password guesses based on a single wordlist. Using a wordlist in a hybrid-style attack, John appends and prepends characters, and attempts dictionary words forward, backward, and typed in twice. It even truncates dictionary terms and appends and prepends characters to the resulting strings. This capability lets the tool create many combinations of password guesses, foiling most users' attempts to create strong passwords by slightly modifying dictionary terms. Quite simply, John has the best hybrid guessing engine available publicly today.

With all of this slicing and dicing of words to create password guesses, John acts like a dictionary food processor. The process of creating permutations for password guesses is defined in a user-configurable rule set. The default rules that John ships with are exceptionally good, and most users won't have to tinker with them.

When conducting a password-cracking attack, John supports several different modes of operation, including the following:

  • "Single-crack" mode. This mode is the fastest and most limited mode supported by John. It bases its guesses only on information from the user account, including the account name and General Electric Computer Operating System (GECOS) field, a block of arbitrary text associated with each account.
  • Wordlist mode. As its name implies, this mode guesses passwords based on a dictionary, creating numerous permutations of the words using the rule set.
  • Incremental mode. This is John's mode for implementing a complete brute-force attack, trying all possible character combinations as password guesses. A brilliant feature of this mode is to use character frequency tables to ensure the most widely used characters (such as e in English) have a heavier weighting in the guessing.
  • External mode: You can create custom functions to generate guesses using this external mode.

By default, John starts using single-crack mode, moves onto wordlist mode, and finally tries incremental mode. Even in the face of all of this flexibility, John's default values are well tuned for most password-cracking attacks. By simply executing the John program and feeding it an unshadowed password file, the attacker can quickly and easily crack passwords, as shown in Figure 7.26.

Figure 7.26

Figure 7.26 Running John the Ripper to crack passwords.

While John is running, it displays successfully cracked passwords on the screen, and stores them in a local file called john.pot. If you ever run John, make sure you clean up after yourself by removing john.pot! Whenever I'm doing a security assessment, I always look for leftover john.pot files that a lazy system administrator or auditor forgot to destroy. Using a remnant john.pot, I can rely on the password-cracking work having been done by another user, making my attack go much more quickly. Also, while John is running, the attacker can press any key on the keyboard to get a one-line status check, which displays the amount of time John has been running, the percentage of the current mode that is completed, as well as the current password guess John has just created.

Defenses Against Password-Cracking Attacks

Cain and John the Ripper represent the best of breed password-cracking tools, and can quickly determine passwords in most environments. In my experience at numerous organizations, Cain or John often return dozens of passwords after running for a couple of minutes. Given the obvious power of these cracking tools, together with the widespread use of passwords as security tools, how can we successfully defend our systems? To defend against password-cracking attacks, you must make sure your users do not select passwords that can be easily guessed by an automated tool. Carefully apply several defensive techniques that work together to help eliminate weak passwords, starting with establishing an effective password policy.

Strong Password Policy

A strong password policy is a crucial element in ensuring the security of your systems. Your organization must have an explicit policy regarding passwords, specifying a minimum length and prohibiting the use of dictionary terms. Passwords should be at least nine characters long, and should be required to include nonalphanumeric characters. In fact, I prefer having a minimum password length of at least 15 or even more characters. I know what you are thinking: "There'd be riots in the cubicles if I configured a minimum password length of 15 characters!" However, we need to get our users out of the mindset of having passwords, and move them into the notion of passphrases. For example, a password of "Gee, I think I'll buy another copy of Counter Hack!" is a lot harder to crack than a password of #dx92!$XA, and the former is a lot easier to type as well. Also, I didn't arbitrarily choose that 15-character minimum. As it turns out, on Windows 2000 and later, if you set a password to 15 characters or more, the system will not store a LM hash at all for that password, instead relying solely on the stronger NT hash in the SAM database. That automatically gets rid of the scourge of LM hashes for such accounts, significantly improving your password security in a Windows environment. We look at an additional LM purging capability shortly.

Furthermore, passwords should have a defined maximum lifetime of 90, 60, or 30 days, depending on the particular security sensitivity and culture of your organization. I tend to recommend a 60- or 90-day policy, because, in my experience, users nearly always write down passwords that expire every 30 days on sticky notes. Of course, your culture might vary. Finally, make sure that your password policy is readily accessible by employees on your internal network and through employee orientation guides.

User Awareness

To comply with your password policy, users must be aware of the security issues associated with weak passwords and be trained to create memorable, yet difficult-to-guess passwords. A security awareness program covering the use of passwords is very important. Such a program could take several forms, ranging from posters in the workplace to explicit training for users in how to create good passwords and protect them.

In your password awareness program (as well as your password policy), tell users how to create good difficult-to-guess passwords. If you don't opt for passphrases, you should alternatively recommend that users rely on the first letters of each word from a memorable phrase, mixing in numbers and special characters. When training users in selecting good passwords, I like to use an example from the theme song from the television show Gilligan's Island: "Just sit right back, and you'll hear a tale, a tale of a fateful trip." A password derived from this phrase would be Jsrb,Ayhat,atoaft. As you might recall, there were seven stars in the TV program, so, we can add that information to the password, coming up with Jsrb,Ayhat,atoaft7*, which would be reasonably difficult to guess, as it contains alphabetic and numeric characters, mixed cases, and special characters. Using the same technique, your users should be able to create their own memorable passwords. Of course, if you use this example from Gilligan's Island in your own awareness initiatives, make sure to warn your users not to set their password to the example Jsrb,Ayhat,atoaft7*, because if you don't warn them, a large number of them will just use the password from your example!

Password Filtering Software

To help make sure users do not select weak passwords, you can use password filtering tools that prevent them from setting their passwords to easily guessed values. When a user establishes a new account or changes his or her password on a system, these filtering programs check the password to make sure that it meets your organization's password policy (i.e., the password is sufficiently complex and is not just a variation of the user name or a dictionary word). With this kind of tool, users are far less able to create passwords that are too easily guessed. However, by being creative enough, some users will be able to come up with something that gets through the password filter yet is still easily crackable. However, the vast majority of your user population will have strong passwords, significantly improving the security of your organization.

For filtering software to be effective, it must be installed on all servers where users establish passwords, including UNIX servers, Windows Domain Controllers, and other systems. Many modern variants of UNIX include password-filtering software. For those that do not, you can use a variety of third-party tools to add this capability, including a pluggable authentication module (PAM) tool written by Solar Designer, the author of John the Ripper. This module is available for Linux, Solaris, and FreeBSD systems for free at www.openwall.com/passwdqc.

For Windows environments, you can select from numerous password filtering tools as well, including the following:

Where Possible, Use Authentication Tools Other Than Passwords

Of course, one of the main reasons we have this password-cracking problem in the first place is our excessive use of traditional reusable passwords. If you get rid of access through passwords, you deal a significant blow to attackers trying to utilize password-cracking programs. For particularly sensitive systems or authentication across untrusted networks, you should avoid using traditional password authentication. Instead, consider one-time password tokens or smart cards for access. Or, utilize biometric authentication to augment passwords, such as handprint, fingerprint, or retina scanners.

Conduct Your Own Regular Password-Cracking Tests

To make sure your users are selecting difficult-to-guess passwords and to find weak passwords before an attacker does, you should conduct your own periodic password-cracking assessments. Using a high-quality password-cracking tool, like Cain or John the Ripper, check for crackable passwords every month or every quarter. As always, avoid using programs from untrusted sources.

Before conducting this type of assessment, make sure you have explicit permission from management. Otherwise, you could damage your career path by cracking the password of some very cranky employees, possibly in senior management positions. When weak passwords are discovered, make sure you have clearly defined, management-approved procedures in place for interacting with users whose passwords can be easily guessed. Don't e-mail or call them on the phone to tell such users to change their passwords, because you'd then make them more subject to social engineering attacks. Instead, configure their accounts to require a password change the next time they log in.

Protect Your Encrypted or Hashed Password Files

A final very important technique for defending against password-cracking tools is to protect your encrypted or hashed passwords. If the attackers cannot steal your password file or SAM database, they will not be able to crack your passwords en masse. You must carefully protect all system backups that include password files (or any other sensitive data, for that matter). Such backups must be stored in locked facilities and possibly encrypted. Similarly, lock up any system recovery floppy disks in a safe location.

On all of your UNIX systems that support it, make sure that you activate password shadowing, which stores the password representations in the /etc/shadow file, readable only by root. On Windows machines, if you do not have to support backward compatibility for Windows for Workgroups or Windows 95 or 98 clients, disable the incredibly weak LM authentication. In an environment that includes only Windows NT and later machines, you can get rid of the weak LM representations by defining the registry key HKEY_LOCAL_MACHINE\SYSTEM\CurrentControlSet\Control\Lsa\NoLMHash on all systems. This registry key tells the system not to store the LM representation when each user next changes his or her password. Thus, with this key defined, your LM hashes will gradually disappear as each user's password expires over the next 90, 60, or 30 days. Furthermore, the registry key HKEY_LOCAL_MACHINE\SYSTEM\CurrentControlSet\
Control\Lsa\LMCompatibilityLevel can be set to a value of three on Windows NT and later clients to force them to send the more difficult-to-crack NTLMv2 representations across the network. This same registry key can be set on servers to a value of five to force them to accept only NTLMv2 authentication, again breaking backward compatibility with Windows for Workgroups, Windows 95, and Windows 98, but significantly improving your security.

Finally, whenever you make a backup using the Ntbackup.exe program, remember to delete or alter the permissions on the copy of the SAM database stored in the %systemroot%\repair\sam._ file. Using these techniques, you can significantly lower the chances of an attacker grabbing your password hashes.

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