Working memory (WM) performance can be improved by an informative cue presented during storage. This effect, termed a retro-cue benefit, can be used to explore mechanisms of attentional prioritization in WM. Directing attention to a single item stored in memory is known to increase memory precision while decreasing the likelihood of incorrect item reports and random guesses, but it is unclear whether similar benefits manifest when participants direct attention to multiple items stored in memory. We tested this possibility by quantifying memory performance when participants were cued to prioritize one or two items stored in working memory. Consistent with prior work, cueing participants to prioritize a single memory item yielded higher recall precision, fewer swap errors, and fewer guesses relative to a neutral cue condition. Conversely, cueing participants to prioritize two memory items yielded fewer swap errors relative to a neutral condition, but no differences in recall precision or guess rates. Although swap rates were less likely during the cue-two vs. neutral conditions, planned comparisons revealed that when participants made swap errors during cue-two trials they were far more likely to confuse two prioritized stimuli than they were to confuse a prioritized stimulus vs. a non-prioritized stimulus. Our results suggest that it is possible to prioritize multiple items stored in memory, with the caveat that doing so may increase the probability of confusing prioritized items.