The ability of biological materials to respond to a diverse range of input stimuli is a result of their intricate, often hierarchical designs that utilize functional materials spanning various chemical length scales. So far, chemists and engineers have encountered significant challenges not only in replicating the functionality of individual materials, but also in controlling their spatial distributions within multi-material systems. The utilization of stimuli-responsive polymers in additive manufacturing (3D-printing) is promising for creating more complex designs with enhanced functionalities. Nevertheless, the development of new stimuli-responsive materials and the establishment of optimal process parameters for their incorporation into additive manufacturing remains a formidable task. To address these challenges, I will share two stories related to our efforts in material and print technology design, aiming to access more complex and functional materials. In the first story, I will describe force-sensitive polymers containing a chain-centered alicyclic diimide moiety capable of undergoing a force-induced retro-Diels-Alder reaction to produce polymers with reactive chain ends. In the second story, I will discuss the optimization of the synthesis for a degradable poly(olefin sulfone) and the design of powder melt-extrusion 3D printers and processes targeting the creation of materials with gradient porosities.