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.