Trying to guess what the correct answer to a question might be can facilitate future learning of this answer when presented in the form of corrective feedback. One issue that determines the effectiveness of guessing as a learning strategy is the timing of the presentation of feedback: it can be presented either immediately after the guess, or after a delay. Whereas the timing of feedback is of little importance for complex materials such as trivia questions, previous research suggests that for simpler materials such as related word pairs guessing seems to benefit learning only when feedback is immediate. In order to test whether this always has to be the case, we conducted two experiments in which we increased the richness of study materials by superimposing the to-be-learned word pairs over unrelated context pictures. We then manipulated the match between contexts at study and at test (Experiment 1) and at the time of feedback delivery (Experiment 2). Contrary to previous studies showing no benefits of guessing with delayed feedback, our results show that learning related word pairs can benefit from guessing even when feedback is delayed. These benefits of guessing occur if participants are reminded via reinstated contexts of the guessing stage at the time of feedback delivery. Our results help constrain theories of guessing benefits and extend theories of reminding.