Synthetic methodologies based on cycle expansion reactions have proven to be highly effective in delivering valuable medium-sized cycles and macrocycles. A primary method of ring expansion relies on intramolecular transamidation reactions. These reactions typically employ N-aminoalkyl and N-aminoacyl derivatives of lactams and their analogues as starting materials, yielding a diverse spectrum of unique nitrogen-containing heterocycles. This Review aims to provide a comprehensive analysis of the research outcomes related to intramolecular transamidation reactions that lead to cycle expansion. This will offer the reader a perspective on the potential applications of such reactions in generating novel and intriguing types of heterocyclic systems.