The Confessions of A White Hat Hacker

Using downloaded hacker utilities, Jude probes his network - and goes undetected

Last week, I spent most of my time installing Linux and a few white hat applications from hacker Web sites: Firewalk, Nmap, Sniffit, Swatch and Tripwire. This week, I've had a bit of a chance to play around with them.

This "white hat" nomenclature confused me when I first heard it. White hat is a fairly common term for people who hack legitimately - security staff, researchers and so on. By contrast, black hat hackers hack maliciously. Basically, white hats are the good guys; black hats are the bad guys. Gray hats are somewhere between the two, and nobody knows where Red Hat Linux fits in with all this.



Intrusion detection software: Specialized security programs that monitor log-on attempts, security logs and other information to try to detect unauthorized attempts to access the corporate network.

TCP/IP fingerprinting: The process of analyzing the TCP/IP protocol stack of a target host computer on a network to discover its operating system and version.

Ping: This utility for TCP/IP-based networks sends a query packet to a target network user or host address and waits for a reply to confirm its presence on the network.


The PacketStorm Web site bills itself as an online security library. Follow this link to download the Firewalk program.

Visit this hacker Web site to download the Nmap program.

This link takes you to the Sniffit packet-sniffer utility, available from Proditti Network Security Co. in Parma, Italy.

Visit this site to download Swatch, a log analyzer, and Tripwire, a file-integrity checker program.


I'm told the terms come from the early Western movies. Because the movies were filmed in black and white, the chase scenes tended to get a bit confusing, until someone decided to give the good guys white hats and the bad guys black hats. Anyway, back to Linux.

Frills and Thrills

Nmap impressed me. It's simple, it's powerful, and it does exactly what it says it does: It maps your network. The author, who goes only by the name Fyodor, even includes a short but well-written HTML manual in a choice of five languages. The program is freeware, so you've got to admire the amount of work that he's put into it.

Nmap runs ping sweeps to find out what machines are connected to your local network, a port scan to find out what services each machine is running and TCP/IP fingerprinting to find out what operating system each is running. The result is a log file giving you a reasonably complete list of what's on your network and what it's doing. That's useful information both for a security manager and any hacker.

We also run Internet Scanner from Atlanta-based Internet Security Systems Inc. (ISS). Internet Scanner can do exactly what Nmap can do and much more. The big difference between the tools - apart from the fact that Nmap is free and Internet Scanner most certainly isn't - is the slant each puts on this function.

The ISS tool gives a much more user-friendly graphical user interface (GUI), advertises its presence to anyone being scanned and so on. It's clearly designed to fit into a corporate environment.

Nmap, on the other hand, is designed for technical staffers who want to dispense with the frills: It's much faster, and it's designed to be run in "stealth mode" so as to avoid detection by intrusion detection software. It certainly snuck in beneath the radar of our intrusion detection software, RealSecure from ISS. That's something we'll have to sort out.

Sniffing for Hack Attacks

Next up was Sniffit, a network packet sniffer. Packet sniffers are rather intriguingly named pieces of software that monitor network traffic.

Under many networking protocols, data that you transmit gets split into small segments, or packets, and the Internet Protocol address of the destination computer is written into the header of each packet. These packets then get passed around by routers and eventually make their way to the network segment that contains the destination computer.

As each packet travels around that destination segment, the network card on each computer on the segment examines the address in the header. If the destination address on the packet is the same as the IP address of the computer, the network card grabs the packet and passes it on to its host computer.

That's how I think it works, anyway. I'm sure there are many network engineers out there who are champing at the bit to explain the many subtle but important errors I've made (feel free to drop into my forum at Computerworld's online Security Watch Community, (, but frankly, that little model seems to work for me.

Promiscuous Network Cards

Packet sniffers work slightly differently. Instead of just picking up the packets that are addressed to them, they set their network cards to what's known as "promiscuous mode" and grab a copy of every packet that goes past. This lets the packet sniffers see all data traffic on the network segment to which they're attached - if they're fast enough to be able to process all that mass of data, that is. This network traffic often contains very interesting information for an attacker, such as user identification numbers and passwords, confidential data - anything that isn't encrypted in some way.

This data is also useful for other purposes - network engineers use packet sniffers to diagnose network faults, for example, and we in security use packet sniffers for our intrusion detection software. That last one is a real case of turning the tables on the attackers: Hackers use packet sniffers to check for confidential data; we use packet sniffers to check for hacker activity. That has a certain elegant simplicity to it.

I've known of packet sniffers for years, and I've talked about the dangers of attackers using packet sniffers in many a consulting assignment, but like many consultants, I've never actually used one before.

One of the reasons for that is simple fear - I'm not that technical at the best of times, but networking is by far my weakest subject. So I've avoided trying packet sniffers because I expected to get swamped by all sorts of networking jargon and problems that would send me running to our network support guys. I feel embarrassed enough that I can't get my head around the concept of subnet masks, so I don't want to display my greater ignorance if I can possibly avoid it.

The thing that worried me most about Sniffit was how easy it was to install. It took about three commands and three minutes to get this thing installed and running on my Linux machine. It even has a GUI (not exactly pretty, but hey - it's free).

Like Nmap, Sniffit is very easy to use and does exactly what it says it does: It sniffs your network and shows you what sort of data is getting passed around.

I'd recommend that you install a packet sniffer and have a look at what sort of data you can see on your local network. Better still, get one of your network engineers to install it for you. They probably know of better, more professional sniffers and will be able to talk you through some of the data that you see going past. It's an interesting look into exactly what's going on within your network.

Firewalk, Swatch and Tripwire stumped me. I don't yet know what I'm doing wrong, but I can't get these things installed. I may not get around to it, though, because my long-awaited laptop has finally arrived. Now, I can get back on course with all those projects that have been on hold for the past couple of weeks.

• This journal is written by a real security manager, "Jude Thaddeus," whose name and employer have been disguised for obvious reasons. It's posted weekly at and at to help you and your security manager better solve security problems. Contact him at or head to the forums. (Note: Registration required to post message; anyone may read messages. To register for our forums, click here).

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