Because climate can affect xylem cell anatomy, series of intra-annual cell anatomical features have the potential to retrospectively supply seasonal climatic information. In this study, we explored the ability to extract information about water stress conditions from tracheid features of the Mediterranean conifer Juniperus thurifera L. Tracheidograms of four climatic years from two drought-sensitive sites in Spain were compared to evaluate whether it is possible to link intra-annual cell size patterns to seasonal climatic conditions. Results indicated site-specific anatomical adjustment such as smaller and thicker tracheids at the dryer site but also showed a strong climatic imprint on the intra-annual pattern of tracheid size. Site differences in cell size reflected expected structural adjustments against cavitation failures. Differences between intra-annual patterns, however, indicated a response to seasonal changes in water availability whereby cells formed under drought conditions were smaller and thicker, and vice versa. This relationship was more manifest and stable at the dryer site.