Since its introduction by Ilizarov, the distraction osteogenesis technique has been used to treat trauma-related conditions, infections, bone tumors, and congenital diseases, either as methods of bone transport or elongation. One of the major dilemmas for the orthopedic surgeon who performs osteogenic distraction is establishing a reproducible method of assessing the progression of the osteogenesis, enabling the early detection of regenerate failures, in order to effectively interfere during treatment, and to determine the appropriate time to remove the external fixator. Several quantitative monitoring methods to evaluate the structural recovery and biomechanical properties of the bone regenerate at different stages, as well as the bone healing process, are under study. These methods can reveal data on bone metabolism, stiffness, bone mineral content, and bone mineral density. The present review comprehensively summarizes the most recent techniques to assess bone healing during osteogenic distraction, including conventional radiography and pixel values in digital radiology, ultrasonography, bone densitometry and scintigraphy, quantitative computed tomography, biomechanical evaluation, biochemical markers, and mathematical models. We believe it is crucial to know the different methods currently available, and we understand that using several monitoring methods simultaneously can be an ideal solution, pointing to a future direction in the follow-up of osteogenic distraction.