A Pd(II)-catalyzed tandem reaction of aliphatic amides with vinylcyclopropanes (VCPs) was accomplished by merging C(sp3)-H and C-C activation. The reaction of VCP revealed alkenylation/cyclization, followed by ring opening via C-C cleavage, delivering vinyl γ-lactams with (E)-selectivity. The role of ligands, site-selectivity, functional group diversity, mechanistic insight, and synthetic utilities are important practical features.