Whitelisting IP addresses and hostnames allow organizations to employ a default-deny approach to network traffic. Organizations employing a default-deny approach can stop many malicious threats, even including zero-day attacks, because it only allows explicitly stated legitimate activities. However, creating a comprehensive whitelist for a default-deny approach is difficult due to user-supplied destinations that can only be known at the time of usage. Whitelists, therefore, interfere with user experience by denying network traffic to user-supplied legitimate destinations. In this thesis, we focus on creating dynamic whitelists that are capable of allowing user-supplied network activity. We designed and built a system called Harbinger, which leverages user interface activity to provide contextual information in which network activity took place. We built Harbinger for Microsoft Windows operating systems and have tested its usability and effectiveness on four popular Microsoft applications. We find that Harbinger can reduce false positives-positive detection rates from 44%-54% to 0%-0.4% in IP and DNS whitelists. Furthermore, while traditional whitelists failed to detect propagation attacks, Harbinger detected the same attacks 96% of the time. We find that our system only introduced six milliseconds of delay or less for 96% of network activity.