We investigate the problem of detecting advanced covert channel techniques, namely victim-aware adaptive covert channels. An adaptive covert channel is considered victim-aware when the attacker mimics the content of its victim’s legitimate communication, such as application-layer metadata, in order to evade detection from a security monitor. In this paper, we show that victim-aware adaptive covert channels break the underlying assumptions of existing covert channel detection solutions, thereby exposing a lack of detection mechanisms against this threat. We first propose a toolchain, Chameleon, to create synthetic datasets containing victim-aware adaptive covert channel traffic. Armed with Chameleon, we evaluate state-of-the-art detection solutions and we show that they fail to effectively detect stealthy attacks. The design of detection techniques against these stealthy attacks is challenging because their network characteristics are similar to those of benign traffic. We explore a deception-based detection technique that we call HoneyTraffic, which generates network messages containing honey tokens, while mimicking the victim’s communication. Our approach detects victim-aware adaptive covert channels by observing inconsistencies in such tokens, which are induced by the attacker attempting to mimic the victim’s traffic. Although HoneyTraffic has limitations in detecting victim-aware adaptive covert channels, it complements existing detection methods and, in combination with them, it can to make evasion harder for an attacker.