The strength of an anonymity system depends on the number of users. Therefore, User eXperience (UX) and usability of these systems is of critical importance for boosting adoption and use. To this end, we carried out a study with 19 non-expert participants to investigate how users experience routine Web browsing via the Tor Browser, focusing particularly on encountered problems and frustrations. Using a mixed-methods quantitative and qualitative approach to study one week of naturalistic use of the Tor Browser, we uncovered a variety of UX issues, such as broken Web sites, latency, lack of common browsing conveniences, differential treatment of Tor traffic, incorrect geolocation, operational opacity, etc. We applied this insight to suggest a number of UX improvements that could mitigate the issues and reduce user frustration when using the Tor Browser.