Successful adaptive behaviors require us to use appropriate levels of cognitive control according to environmental needs. While the decision to engage more control is often ascribed to a strategic resource-intensive executive process, people may also simply use surrounding environmental features to trigger different levels of cognitive control instead. However, there is currently little evidence for such environment-specific triggering of cognitive control. Therefore, we used a forced task-switching paradigm (Study 1) and a free-choice Wisconsin card sorting task (Study 2) to investigate the environment-specific modulation of cognitive control. In both studies, participants were exposed to two environments with different control needs: task-switching frequency in Study 1 and rule volatility in Study 2. The impact of environment was tested in a subsequent, uninstructed probe phase, where the actual task switching frequency or rule volatility was again equal in both environments, after either one or four days of training. The results showed that, after four days’ training, but not after one, participants showed an environment-specific triggering of cognitive control in both studies. Specifically, participants showed a reduced switch cost in the environment that triggered a high need for control in Study 1, and higher learning rates in the environment that indicated a high rule volatility, especially after receiving negative feedback in Study 2. Taken together, these results provided important evidence for the idea that the modulation of cognitive control in both forced and free choice behavior can rely on associative learning, providing an environmental triggering mechanism for cognitive control.