Many organizations collect data that would be useful to public researchers, but cannot be shared due to promises of confidentiality to those that participated in the study. This thesis evaluates the risks and utility of several existing release methods, as well as develops new ones with different risk/utility tradeoffs. In Chapter 2, I present a new risk metric, called model-specific probabilistic differ- ential privacy (MPDP), which is a relaxed version of differential privacy that allows the risk of a release to be based on the worst-case among plausible datasets instead of all possible datasets. In addition, I develop a generic algorithm called local sensitiv- ity random sampling (LSRS) that, under certain assumptions, is guaranteed to give releases that meet MPDP for any query with computable local sensitivity. I demon- strate, using several well-known queries, that LSRS releases have much higher utility than standard differentially private release mechanism, the Laplace Mechanism, at only marginally higher risk. In Chapter 3, using to synthesis models, I empirically characterize the risks of releasing synthetic data under the standard “all but one” assumption on intruder background knowledge, as well the effect decreasing the number of observations the intruder knows beforehand has on that risk. I find in these examples that even in the “all but one” case, there is no risk except to extreme outliers, and even then the risk is mild. I find that the effect of removing observations from an intruder’s background knowledge has on risk heavily depends on how well that intruder can fill in those missing observations: the risk remains fairly constant if he/she can fill them in well, and the risk drops quickly if he/she cannot. In Chapter 4, I characterize the risk/utility tradeoffs for an augmentation of synthetic data called fidelity measures (see Section 1.2.3). Fidelity measures were proposed in Reiter et al. (2009) to quantify the degree to which the results of an analysis performed on a released synthetic dataset match with the results of the same analysis performed on the confidential data. I compare the risk/utility of two different fidelity measures, the confidence interval overlap (Karr et al., 2006) and a new fidelity measure I call the mean predicted probability difference (MPPD). Simultaneously, I compare the risk/utility tradeoffs of two different private release mechanisms, LSRS and a heuristic release method called “safety zones”. I find that the confidence interval overlap can be applied to a wider variety of analyses and is more specific than MPPD, but MPPD is more robust to the influence of individual observations in the confidential data, which means it can be released with less noise than the confidence interval overlap with the same level of risk. I also find that while safety zones are much simpler to compute and generally have good utility (whereas the utility of LSRS depends on the value of ε), it is also much more vulnerable to context specific attacks that, while not easy for an intruder to implement, are difficult to anticipate.