Can modifying the training data distribution guide optimizers toward solutions with improved generalization when training large language models (LLMs)? In this work, we theoretically analyze an in-context linear regression model with multi-head linear self-attention, and compare the training dynamics of two gradient based optimizers, namely gradient descent (GD) and sharpness-aware minimization (SAM), the latter exhibiting superior generalization properties but is prohibitively expensive for training even medium-sized LLMs. We show, for the first time, that SAM induces a lower simplicity bias (SB)-the tendency of an optimizer to preferentially learn simpler features earlier in training-and identify this reduction as a key factor underlying its improved generalization performance. Motivated by this insight, we demonstrate that altering the training data distribution by upsampling or augmenting examples learned later in training similarly reduces SB and leads to improved generalization. Our extensive experiments show that our strategy improves the performance of multiple LLMs-including Phi2-2.7B , Llama3.2-1B, Gemma3-1B-PT, and Qwen3-0.6B-Base-achieving relative accuracy gains up to 18% when fine-tuned with AdamW and Muon on mathematical reasoning tasks.