Anonymizing internet-based traffic

Ensuring your identity is kept secret during a penetration test is important to prevent the target from knowing who is collecting information about them. However, during the reconnaissance phase of the Cyber Kill Chain^® (covered in Chapter 1), you may be using various tools to help automate the information-gathering process. These tools will generate traffic and contain your source IP address within each packet that leaves your device.

For instance, you’re performing a port scan on a targeted web server to identify open ports and running services. When the port scanner tool on your device sends specially crafted packets (probes) to the targeted web server, each probe will contain your source IP address, which can be used to identify your geolocation. The targeted web server will generate log messages on each transaction it performs and will contain a record of all source IP addresses, including yours. Targets can identify and counteract...