Honeypots for Windows (Books for Professionals by Professionals)

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Chapter 4 - Windows Honeypot Deployment
Honeypots for Windows
by Roger A. Grimes
Apress 2005

Although you can deploy a honeypot without much forethought, your life will be easier if you do it the right way the first time. This section outlines the installation steps and offers some tips to make your honeypot installation go smoothly.

Installation Steps

When installing a Windows honeypot, here are the general steps you can take to deploy and operate your honeypot:

  1. Decide on its physical placement (as discussed in Chapter 2).

  2. Install your chosen Windows OS on the host computer.

  3. Harden Windows installation (see the “Hardening Microsoft Windows” section later in this chapter).

  4. Install applications, services, and so on (including honeypot and VM software, if needed).

  5. Create content and develop a content update plan.

  6. Install monitoring tools (see Chapters 9 and 10).

  7. Test your honeypot.

  8. Make changes based on your test results, if needed.

  9. Document configuration settings (see Chapters 10 and 11).

  10. Clear any local log files and make a backup copy or image of your honeypot system.

  11. Take baseline measurements (see Chapter 10).

  12. Deploy your honeypot system in a live environment.

  13. Monitor your honeypot and begin operational procedures.

Note 

If you use an existing hard drive in your honeypot that was previously used in a production system, consider formatting and/or running a data-wiping utility to remove previous data remnants.

Several of these steps require some explanation. The following sections provide more details about testing your honeypot (step 7), documenting configuration settings (step 9), and taking baseline measurements (step 11).

Testing Your Honeypot

Testing your honeypot (step 7) is an important step. You want to “attack” your honeypot as if you were an intruder. If you left a particular vulnerability open, attempt to exploit it. Test your alerting mechanisms to make sure they alert you in the event of a compromise. Test your monitoring tools. If you hardened any particular area of the honeypot to prevent a particular compromise, try to compromise it. Use vulnerability assessment tools against your honeypot and employ trusted friends or coworkers to test the honeypot. If you find something not working, fix it, and then test again. The key is that you don’t want the first test of the honeypot to be a real hacker’s compromise against your system on a live environment. Testing will be covered in more detail in Chapter 12.

Documenting Configuration Settings

Documenting configuration settings (step 9) is important because you need to know what changes have been made by the hacker or malicious exploit, as compared to your honeypot’s uncompromised state. And if you need to rebuild the honeypot or improve it, you have a handy document detailing what was done to build the original honeypot.

Taking Baseline Measurements

Taking baseline measurements (step 11) is the process of measuring what the honeypot looks like prior to compromise. Although covered in detail in Chapter 10, here are some of the methods for getting baseline measurements:

If you haven’t run these types of utilities before, you’ll be surprised that a lot of activity is occurring, even on a system that appears to be idle. And if you don’t know what the uncompromised state looks like, how can you be sure what the compromised state looks like? Chapter 10 will cover many of these tools in detail.

Listing 4-1 shows an example of listing which programs are in the auto-run areas.

Honeypot Installation Tips

When installing your honeypot, you should follow Microsoft’s typical installation procedures, but there are some special considerations.

General Installation Guidelines

Here are some tips that apply to all types of honeypot systems:

VM Honeypot Installation Guidelines

If you are using VM software to run your honeypot, use these guidelines as well:

Note 

VMware may not support the use of arbitrary MAC addresses (see http://www.vmware.com/support/ws4/doc/network_macaddr_ws.html).

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