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Remote password guessing attacks remain one of the largest sources of account compromise. Understanding and characterizing attacker strategies is critical to improving security but doing so has been challenging thus far due to the sensitivity of login services and the lack of ground truth labels for benign and malicious login requests. We perform an in-depth measurement study of guessing attacks targeting two large universities. Using a rich dataset of more than 34 million login requests to the two universities as well as thousands of compromise reports, we were able to develop a new analysis pipeline to identify 29 attack clusters—many of which involved compromises not previously known to security engineers. Our analysis provides the richest investigation to date of password guessing attacks as seen from login services. We believe our tooling will be useful in future efforts to develop real-time detection of attack campaigns, and our characterization of attack campaigns can help more broadly guide mitigation design.