Cerebellar peduncles (CPs) are white matter tracts connecting the cerebellum to other brain regions. Automatic segmentation methods of the CPs have been proposed for studying their structure and function. Usually the performance of these methods is evaluated by comparing segmentation results with manual delineations (ground truth). However, when a segmentation method is run on new data (for which no ground truth exists) it is highly desirable to efficiently detect and assess algorithm failures so that these cases can be excluded from scientific analysis. In this work, two outlier detection methods aimed to assess the performance of an automatic CP segmentation algorithm are presented. The first one is a univariate non-parametric method using a box-whisker plot. We first categorize automatic segmentation results of a dataset of diffusion tensor imaging (DTI) scans from 48 subjects as either a success or a failure. We then design three groups of features from the image data of nine categorized failures for failure detection. Results show that most of these features can efficiently detect the true failures. The second method - supervised classification - was employed on a larger DTI dataset of 249 manually categorized subjects. Four classifiers - linear discriminant analysis (LDA), logistic regression (LR), support vector machine (SVM), and random forest classification (RFC) - were trained using the designed features and evaluated using a leave-one-out cross validation. Results show that the LR performs worst among the four classifiers and the other three perform comparably, which demonstrates the feasibility of automatically detecting segmentation failures using classification methods.