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Two novel representatives of energetic (1,2,4-triazolyl)furoxans were prepared from the readily available (furoxanyl)amidrazones. Synthesized compounds were thoroughly characterized with IR and multinuclear NMR spectroscopy, elemental analysis and X-ray diffraction data. Analysis of structural features supported by quantum-chemical calculations revealed the main reasons for experimentally observed difference in thermal stability and mechanical sensitivity of both compounds. It was found that 3-cyano-4-(1H-1,2,4-triazol-3-yl)furoxan is more thermally stable (Td: 229 ​°C) than 4-azido-3-(1H-1,2,4-triazol-3-yl)furoxan (Td: 154 ​°C) and the latter compound is also more sensitive to impact and friction. In addition, both heterocyclic assemblies have high detonation parameters (vD: 7.0–8.0 ​km·s−1; p: 22–29 ​GPa) exceeding those of benchmark explosives trinitrotoluene and hexanitrostilbene which enable their usability for various energetic applications.