Electrospinning and electrospun fibrous assemblies have attracted interest in a variety of biomedical fields including woundcare, tissue engineering and drug delivery, due to the large surface-area-to-volume ratio and high porosity of nanofibrous webs. Normally, wound dressings are manufactured well before the point of care, and then packaged and distributed for use at a later stage. More recently, in situ electrospinning of fibers directly onto wound sites has been proposed as a route to personalized wound dressing manufacture, tailored to the needs of individual patients. Practically, in situ deposition of nanofibers on to a wound could be envisaged using a portable or hand-held electrospinning device that is safe and easy to operate. This review focuses on recent advances in portable electrospinning technology and potential applications in woundcare and regenerative medicine. The main research challenges and future trends are also considered.