The study analyzes open hole carbon fiber reinforced polymer CFRP laminates modified with electrospun interleaves containing Diels Alder-based self-healing agents. It develops a high-fidelity simulation framework to investigate the quasistatic tensile behavior of these composites. The study uses Hashin's failure criteria to capture intralaminar damage and surface-based cohesive contact interactions to model interlaminar delamination. Two interleave configurations are examined: solution electrospinning (SEP) for full thickness coverage and melt electrospinning (MEP) for localized reinforcement. Results show good agreement with experimental data, capturing key failure mechanisms like matrix cracking, fiber breakage, and delamination. The study emphasizes the importance of spatially resolved cohesive properties and meshing strategies in accurately simulating damage progression.