The reaction of cyanogen azide with strained‐ring containing primary and secondary amines led to the isolation of energetic molecules deriving their energy content from both strained rings as well as aminotetrazoles. Azo‐coupling of these materials afforded novel high‐nitrogen energetic materials of very high sensitivity. All compounds were chemically characterized by IR, NMR, single‐crystal X‐ray crystallography, and high‐resolution mass spectrometry. Their impact and friction sensitivities were experimentally determined, and their energetic performances were calculated.