Irregular conflict–terrorism, insurgency, and criminal warfare (“criminal insurgency” and transnational organized crime)–is a complex challenge to many states. Ranging from street gangs–”local insurgencies” to drug/crime wars or “criminal insurgencies” through transnational criminal or extremist networks challenging regions–these threats require intelligence and analysis to understand and forecast potentials and craft interagency, intergovernmental solutions. Adaptive, analytical red teaming is a process of refining tradecraft for indications and warning (for a range of scenarios along the spectrum of current intelligence, early warning through strategic foresight). Specifically, analytical red teaming places a team of analysts against an active red team simulating a criminal opposing force, or forces. This short paper will describe the process and briefly recap the experience of two adaptive, analytical red team exercises (Operation Talavera and Operation Chimera) conducted by the Los Angeles Terrorism Early Warning (TEW) Group. Lessons learned and suggestions for refining the process, as well as conducting future red team exercises for irregular threats, will be discussed.