Research regarding how people monitor their learning has shown that ease of processing strongly guides people's judgments of learning (JOLs). However, the desirable difficulties concept (Bjork, 1994) suggests that studying information that is less fluent can result in greater learning. Currently, it is unclear whether people are aware of the potential benefits of desirable difficulties during learning. To address this, in Experiment 1, participants studied inverted and upright words and also made JOLs. While participants' JOLs did not differ for inverted and upright words, recall was greater for inverted words. Experiment 2 used several study-test cycles in which participants could potentially learn about the beneficial effects of processing inverted words with task experience, and similar results were obtained. Thus, reading inverted words requires processing that enhances recall, but memory predictions do not differentiate between upright and inverted words. We interpret these results in terms of processing fluency, desirable difficulties, and theories of metacognitive monitoring.