Outflank Security Tooling (OST) by Core Security is a set of tools created by red teaming specialists. OST bundles internal tools and makes them available as a service for high-end offensive security services such as red teaming, adversary simulation, or advanced penetration testing services. These tools simulate techniques used by APTs and Organized Crime Groups, not available in public tools. OST enables team members to perform deep-technical tasks easily and safely. It is developed to bypass defensive measures and detection tools, enhancing the efficiency of offensive security teams. OST is continuously updated with new offensive techniques and procedures by a team of hackers and developers, saving significant time in developing and maintaining a full internal toolkit. The toolkit enhances capabilities in initial access, EDR evasion, and OPSEC-safe lateral movement, featuring techniques not yet published or weaponized by other red teams. OST integrates directly with Cobalt Strike through BOFs and reflective DLL loading techniques, enabling efficient post-exploitation tasks. Live demos of the OST toolkit are available upon request.