This review addresses the rationale of recurrent and/or residual caries associated with resin composite restorations alongside current strategies and evidence-based recommendations to arrest residual caries and restrain recurrent caries. The PubMed and MEDLINE databases were searched for composite-associated recurrent/residual caries focusing on predisposing factors related to materials and operator’s skills; patient-related factors were out of scope. Recurrent caries and fractures are the main reasons for the failure of resin composites. Recurrent and residual caries are evaluated differently with no exact distinguishment, especially for wall lesions. Recurrent caries correlates to patient factors, the operator’s skills of cavity preparation, and material selection and insertion. Material-related factors are significant. Strong evidence validates the minimally invasive management of deep caries, with concerns regarding residual infected dentin. Promising technologies promote resin composites with antibacterial and remineralizing potentials. Insertion techniques influence adaptation, marginal seal, and proximal contact tightness. A reliable diagnostic method for recurrent or residual caries is urgently required. Ongoing endeavors cannot eliminate recurrent caries or precisely validate residual caries. The operator’s responsibility to precisely diagnose original caries and remaining tooth structure, consider oral environmental conditions, accurately prepare cavities, and select and apply restorative materials are integral aspects. Recurrent caries around composites requires a triad of attention where the operator’s skills are cornerstones.