This article explores methods used to obtain a higher validity in estimates of the prevalence of undeclared work in Germany in surveys within the general population. Using an experimental design two “dejeopardizing” techniques are compared as alternatives to direct questioning when asking sensitive questions: the randomized response technique (RRT) and the item count technique (ICT). These techniques were specifically developed to reduce misreporting on sensitive topics: The goal is to elicit a higher proportion of honest answers from respondents by increasing the anonymity of the question-and-answer process. Our results suggest that neither RRT nor ICT provide unambiguous results with respect to more successful elicitation of reports of socially undesirable behavior. In addition, the theoretically significant influence of background variables is investigated empirically by means of multiple regression. Factors which foster illicit work are, aside from opportunity structures, social norms, which contribute significantly to the explanation of individual decisions to engage in undeclared work.