Pretesting, or answering a question prior to learning the associated information is a powerful tool for learning. By the nature of this type of test, learners are likely to answer a question wrong. In this dissertation, I will explore the idea that the incorrect guesses may lead to competition (i.e., source monitoring and/or cue overload/ response competition) between the correct answer and the incorrect guess. If this is the case, any benefit of pretesting is found in spite of this potential competition, and making more incorrect guesses should lead to worsened performance compared to making a single guess. However, theories behind the pretesting benefit (i.e., Retrieval Effort Hypothesis, Elaborative Retrieval Hypothesis, Episodic Context Account) would all predict the opposite- that making multiple guesses in response to a pretest question would lead to an increase in benefit for later memory. Three experiments were conducted here to determine situations in which generating more guesses as responses to pretest questions will be beneficial or detrimental for learning. Experiment 1 compared the effects of one and three pretest guesses to a read-only control on a final, cued-recall test. Experiment 2 replicated experiment 1 and added a comparison condition in which participants were exposed to prior participants’ guesses. Experiment 3 replicated Experiment 1 with the final test changed to multiple-choice and timing being recorded and analyzed across conditions. Across the three experiments, a consistent benefit of making pretesting guesses was found, however, no additional benefit or detriment was found for conditions in which three guesses were made as opposed to one. In short, despite clear reasons derived from the literature to expect that memory might be improved or impaired by the inclusion of extra guesses, no evidence was found to suggest that this is the case. This has important practical implications for teachers and learners looking to implement pretest guessing into their instruction and study strategies as well as implications for the theoretical understanding of the pretesting effect.