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Proper use of an anonymity system requires adequate understanding of how it functions. Yet, there is surprisingly little research that looks into user understanding and usage of anonymity software. Improper use stemming from a lack of sufficient knowledge of the system has the potential to lead to deanonymization, which may hold severe personal consequences for the user. We report on the understanding and the use of the Tor anonymity system. Via semistructured interviews with 17 individuals (6 experts and 11 non-experts) we found that experts and non-experts view, understand, and use Tor in notably different ways. Moreover, both groups exhibit behavior as well as gaps in understanding that could potentially compromise anonymity. Based on these findings, we provide several suggestions for improving the user experience of Tor to facilitate better user understanding of its operation, threat model, and limitations.