Redacted emails satisfy most privacy requirements but they make it more difficult to detect anomalous emails that may be indicative of data exfiltration. In this paper we develop an enhanced method of Active Learning using an information gain maximizing heuristic, and we evaluate its effectiveness in a real world setting where only redacted versions of email could be labeled by human analysts due to privacy concerns. In the first case study we examined how Active Learning should be carried out. We found that model performance was best when a single highly skilled (in terms of the labelling task) analyst provided the labels. In the second case study we used confidence ratings to estimate the labeling uncertainty of analysts and then prioritized instances for labeling based on the expected information gain (the difference between model uncertainty and analyst uncertainty) that would be provided by labelling each instance. We found that the information maximization gain heuristic improved model performance over existing sampling methods for Active Learning. Based on the results obtained, we recommend that analysts should be screened, and possibly trained, prior to implementation of Active Learning in cybersecurity applications. We also recommend that the information gain maximizing sample method (based on expert confidence) should be used in early stages of Active Learning, providing that well-calibrated confidence can be obtained. We also note that the expertise of analysts should be assessed prior to Active Learning, as we found that analysts with lower labelling skill had poorly calibrated (over-) confidence in their labels.