Synthetically augmenting training datasets with diffusion models has become an effective strategy for improving the generalization of image classifiers. However, existing approaches typically increase dataset size by 10-30x and struggle to ensure generation diversity, leading to substantial computational overhead. In this work, we introduce TADA (TArgeted Diffusion Augmentation), a principled framework that selectively augments examples that are not learned early in training using faithful synthetic images that preserve semantic features while varying noise. We show that augmenting only this targeted subset consistently outperforms augmenting the entire dataset. Through theoretical analysis on a two-layer CNN, we prove that TADA improves generalization by promoting homogeneity in feature learning speed without amplifying noise. Extensive experiments demonstrate that by augmenting only 30-40% of the training data, TADA improves generalization by up to 2.8% across diverse architectures including ResNet, ViT, ConvNeXt, and Swin Transformer on CIFAR-10/100, TinyImageNet, and ImageNet, using optimizers such as SGD and SAM. Notably, TADA combined with SGD outperforms the state-of-the-art optimizer SAM on CIFAR-100 and TinyImageNet. Furthermore, TADA shows promising improvements on object detection benchmarks, demonstrating its applicability beyond image classification. Our code is available at https://github.com/BigML-CS-UCLA/TADA.

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