In this talk I will reminisce on collaborations with Prof. Hatton and his group on the development of functional electrospun nanofibers for a variety of applications involving separations, sorption and chemical sensing. Topics include waterproof, breathable fabrics for advanced chemical-biological protection suits, the early development of carbon nanofibers and the subsequent exploration of electrochemical sensing. These early collaborations laid the foundation for subsequent work in other types of electrospun sensors and studies of aerosol separation that continue to this day.