During the Capability Life Cycle (CLC) we estimate using a mix of black-box and white-box techniques. The mix and balance of white-box/black-box technique is dependent on the knowns, unknowns, CLC phase and purpose of the estimate. On one side of the spectrum, the ultimate estimate utilises a complete white-box technique based on a known scope linked to validated requirements, verified quantities and contracts underpinned by a complete Project Documentation Suite that is supported by documented project information and objective quality evidence (OQE) records. On the other side of the spectrum is a complete black-box estimating technique based on concepts and system-solution-class description parameter thresholds. This presentation highlights some key tips, tricks and pitfalls and guidance on how to balance an appropriate mix for your estimating needs. The tips include problem space abstraction methods. The tricks include how to derive figures of merit to quantify systems and life cycle cost effectiveness differentiators. The pitfalls include lessons learnt through experience of applying each of these methods in practice.