Both the operational and academic security communities have used dynamic analysis sandboxes to execute malware samples for roughly a decade. Network information derived from dynamic analysis is frequently used for threat detection, network policy, and incident response. Despite these common and important use cases, the efficacy of the network detection signal derived from such analysis has yet to be studied in depth. This paper seeks to address this gap by analyzing the network communications of 26.8 million samples that were collected over a period of five years. Using several malware and network datasets, our large scale study makes three core contributions. (1) We show that dynamic analysis traces should be carefully curated and provide a rigorous methodology that analysts can use to remove potential noise from such traces. (2) We show that Internet miscreants are increasingly using potentially unwanted programs (PUPs) that rely on a surprisingly stable DNS and IP infrastructure. This indicates that the security community is in need of better protections against such threats, and network policies may provide a solid foundation for such protections. (3) Finally, we see that, for the vast majority of malware samples, network traffic provides the earliest indicator of infection—several weeks and often months before the malware sample is discovered. Therefore, network defenders should rely on automated malware analysis to extract indicators of compromise and not to build early detection systems.