With the increasing prevalence of encrypted network traffic, cyber security analysts have been turning to machine learning (ML) techniques to elucidate the traffic on their networks. However, ML models can become stale as new traffic emerges that is outside of the distribution of the training set. In order to reliably adapt in this dynamic environment, ML models must additionally provide contextualized uncertainty quantification to their predictions, which has received little attention in the cyber security domain. Uncertainty quantification is necessary both to signal when the model is uncertain about which class to choose in its label assignment and when the traffic is not likely to belong to any pre-trained classes. We present a new, public dataset of network traffic that includes labeled, Virtual Private Network (VPN)-encrypted network traffic generated by 10 applications and corresponding to 5 application categories. We also present an ML framework that is designed to rapidly train with modest data requirements and provide both calibrated, predictive probabilities as well as an interpretable "out-of-distribution" (OOD) score to flag novel traffic samples. We describe calibrating OOD scores using p-values of the relative Mahalanobis distance. We demonstrate that our framework achieves an F1 score of 0.98 on our dataset and that it can extend to an enterprise network by testing the model: (1) on data from similar applications, (2) on dissimilar application traffic from an existing category, and (3) on application traffic from a new category. The model correctly flags uncertain traffic and, upon retraining, accurately incorporates the new data.