Mobile handheld devices provide powerful capability and functionality making it prominent within public and private environments, allowing information to be processed inside and outside of the organisation s network. Mobile Bluetooth connectivity allows workers to access information in both personal and corporate environments This book, presents an information security evaluation of a Bluetooth-enabled handheld device. It attempts to understand the implications of using a Bluetooth-enabled handheld device in both public and private environments and the risks presented by a mobile workforce using Bluetooth connectivity. Information security risks are evaluated based on research into vulnerabilities, attacks and tools that exist to compromise a Bluetooth-enabled handheld device, while also suggesting a possible Bluetooth penetration testing methodology. A practical assessment is performed for a critical analysis of the information security mechanisms implemented by the Bluetooth-enabled handheld device (PDA) and determining possible recommendations to mitigate identified risks.