EO/IR windows are a significant challenge for the weapon system sensor designer who must design for high EO performance, low radar cross section (RCS), supersonic flight, durability, producibility and affordable initial and life cycle costs. This is particularly true in the 8 to 12 micron IR band at which window materials and coating choices are limited by system design requirements. The requirements also drive the optimization of numerous mechanical, optical, materials, and electrical parameters. This paper addresses the EO/IR window as a system design challenge. The interrelationship of the optical, mechanical, and system design processes are examined. This paper presents a summary of the test results, trade studies and analyses that were performed for multi-segment, flight-worthy optical windows with superior optical performance at subsonic and supersonic aircraft velocities and reduced radar cross section. The impact of the window assembly on EO system modulation transfer function (MTF) and sensitivity will be discussed. The use of conductive coatings for shielding/signature control will be discussed.