The recent advancements in machine learning have led to a wave of interest in adopting online learning-based approaches for long-standing attack mitigation issues. In particular, DDoS attacks remain a significant threat to network service availability even after more than two decades. These attacks have been well studied under the assumption that malicious traffic originates from a single attack profile. Based on this premise, malicious traffic characteristics are assumed to be considerably different from legitimate traffic. Consequently, online filtering methods are designed to learn network traffic distributions adaptively and rank requests according to their attack likelihood. During an attack, requests rated as malicious are precipitously dropped by the filters. In this paper, we conduct the first systematic study on the effects of data poisoning attacks on online DDoS filtering; introduce one such attack method, and propose practical protective countermeasures for these attacks. We investigate an adverse scenario where the attacker is "crafty", switching profiles during attacks and generating erratic attack traffic that is ever-shifting. This elusive attacker generates malicious requests by manipulating and shifting traffic distribution to poison the training data and corrupt the filters. To this end, we present a generative model MimicShift, capable of controlling traffic generation while retaining the originating traffic's intrinsic properties. Comprehensive experiments show that online learning filters are highly susceptible to poisoning attacks, sometimes performing much worse than a random filtering strategy in this attack scenario. At the same time, our proposed protective countermeasure diminishes the attack impact.