Despite extensive reports on azo dyes, the development of environmentally benign and multifunctional dye systems tailored for technical textiles remains limited. In this work, a green one-pot multicomponent strategy was employed to synthesize a series of pyrano[2,3-c]pyrazole-based monoazo dyes, which were structurally validated by comprehensive spectroscopic and elemental analyses. The dyes exhibited high exhaustion and fixation on polyester, nylon, and wool fabrics, delivering uniform deep shades with strong color strength, excellent fastness properties, and compatibility with high-temperature dyeing without auxiliary fixation steps. Notably, post-dyeing silver nanoparticle functionalization imparted pronounced and durable antimicrobial activity while preserving chromatic performance.