Diabetic peripheral neuropathy is a major complication of diabetes mellitus, and it is the leading cause of foot ulceration and amputations. The Semmes–Weinstein monofilament examination (SWME) is a widely used, low-cost, evidence-based tool for predicting the prognosis of diabetic foot patients. The examination can be quick, but due to the high prevalence of the disease, many healthcare professionals can be assigned to this task several days per month. In an ongoing project, it is our objective to minimize the intervention of humans in the SWME by using an automated testing system relying on computer vision. In this paper we present the project’s first part, constituting a system for automatically identifying the SWME testing sites from digital images. For this, we have created a database of plantar images and developed a segmentation system, based on image processing and deep learning—both of which are novelties. From the 9 testing sites, the system was able to correctly identify most 8 in more than 80% of the images, and 3 of the testing sites were correctly identified in more than 97.8% of the images.