Steering vectors are a lightweight method for controlling language model behavior by adding a learned bias to the activations at inference time. Although effective on average, steering effect sizes vary across samples and are unreliable for many target behaviors. In my thesis, I investigate why steering reliability differs across behaviors and how it is impacted by steering vector training data. First, I find that higher cosine similarity between training activation differences predicts more reliable steering. Second, I observe that behavior datasets where positive and negative activations are better separated along the steering direction are more reliably steerable. Finally, steering vectors trained on different prompt variations are directionally distinct, yet perform similarly well and exhibit correlated efficacy across datasets. My findings suggest that steering vectors are unreliable when the latent target behavior representation is not effectively approximated by the linear steering direction. Taken together, these insights offer a practical diagnostic for steering unreliability and motivate the development of more robust steering methods that explicitly account for non-linear latent behavior representations.