We investigate photon--pion discrimination in regimes where electromagnetic showers overlap at the scale of calorimeter granularity. Using full detector simulations with fine-grained calorimeter segmentation of approximately 0.025×0.025 in (η,ϕ), we benchmark three approaches: boosted decision trees (BDTs) on shower-shape variables, dense neural networks (DNNs) on the same features, and a ResNet-based convolutional neural network operating directly on calorimeter cell energies. The ResNet significantly outperformed both baseline methods, achieving further gains when augmented with soft scoring and an auxiliary ΔR regression head. Our results demonstrate that residual convolutional architectures, combined with physics-informed loss functions, can substantially improve photon identification in high-luminosity collider environments in which overlapping electromagnetic showers challenge traditional methods.