Attentional templates in visual working memory (VWM) are essential for guiding visual search. Although much debate has focused on whether these templates are stored in discrete states or continuous resources, a question remains: To what extent can the priority of a template be strategically tuned to match environmental probabilities? We investigated this flexibility by manipulating the reliability of retro-cues (the probability that a cued item is the target) across three experiments combining memory recall and visual search. Crucially, we tested whether strategic prioritization persists under varying memory loads (two vs. three items). We observed that retro-cue validity affected both search efficiency and memory performance and that these effects were larger under higher cue reliability. This reliability-dependent pattern was clearly present when memory load increased to three items (Experiment 2) and was also observed when item shape signaled the functional role of each representation (Experiment 3). Together, these results show that the influence of a cued representation varies systematically with cue reliability. This pattern is consistent with flexible prioritization but does not distinguish between a continuous adjustment of template strength and probabilistic switching between discrete representational states. Overall, our findings suggest that VWM prioritization is sensitive to expected relevance and adapts to memory load and task structure.