This report provides a comprehensive overview of penetration testing, covering various methodologies, legal considerations, and standard operating procedures (SOP). The report begins by comparing different pen testing methods, including black box, grey box, and white box testing, detailing their characteristics, advantages, and disadvantages. It then delves into the statutory and legal considerations that penetration testers must be aware of, such as laws related to port scanning and the Computer Fraud and Abuse Act, emphasizing the importance of ethical conduct and authorized permissions. Furthermore, the report outlines a Standard Operating Procedure (SOP) for IT security penetration testing, including introductions, purposes, scope, roles, and responsibilities of the testing team, and processes for managing the penetration test. The SOP also specifies the roles of the Pen Test Point of Contact (POC), activities, and procedures involved in a penetration testing project, from introductory briefings to technical meetings and policy reviews. The report highlights the significance of each aspect of the penetration testing process to ensure that the tests are conducted ethically, legally, and effectively.