Efforts to improve dementia care through training occur in an organizational context that may enhance or inhibit improvement. This article used linear mixed models to examine the relationship of contextual and organizational factors to baseline knowledge, work stress, and training outcomes of a dementia care training program. Data from staff (N = 678) in 16 long-term care settings indicate that such factors related to both baseline training needs and training effects over time. On the basis of these findings, long-term care administrators are advised to consider the administrative climate, communication patterns, and the perceived need for training before implementing a training program.