Direct functionalization of C(sp3)-H bonds represents a pivotal objective in the realm of synthetic chemistry. However, the inherent chemical inertness coupled with low reactivity disparities among these bonds presents formidable challenges. The hydrogen atom transfer (HAT)-mediated strategy enables a direct and selective C(sp3)-H functionalization under environmentally benign conditions, exhibits a wider substrate scope and superior functional group tolerance, and occasionally displays complementary reactivity to the transition metal-catalyzed C-H activation. The traditional methods are focused on the utilization of heteroatom radicals and necessitate harsh reaction conditions or specific precursors. In contrast, the vinyl radical-induced HAT, particularly triggered by radical addition to alkynes, is considered more efficient and eco-friendly, thus facilitating their applications in the late-stage modification of complex organic architectures. Over the past decade, significant progresses has been made in this area, including switching from the common 5-exo-trig to uncommon 5-endo-trig, 4-exo-trig, or 6-endo-trig cyclization, and extension from the traditional intramolecular cyclization to intermolecular C(sp3)-H functionalization. This review primarily focuses on the advancements of these new reaction modes since 2013. The reaction mechanisms, merits and limitations, especially the key facts for tuning reaction pathways, are discussed, which may be valuable for the development and application of this methodology.