Functionally distinct memory systems likely evolved in response to incompatible demands placed on learning by distinct environmental conditions. Working memory appears adapted, in part, for conditions that change frequently, making rapid acquisition and brief retention of information appropriate. In contrast, habits form gradually over many experiences, adapting organisms to contingencies of reinforcement that are stable over relatively long intervals. Serial reversal learning provides an opportunity to simultaneously examine the processes involved in adapting to rapidly changing and relatively stable contingencies. In serial reversal learning, selecting one of the two simultaneously presented stimuli is positively reinforced, while selection of the other is not. After a preference for the positive stimulus develops, the contingencies of reinforcement reverse. Naïve subjects adapt to such reversals gradually, perseverating in selection of the previously rewarded stimulus. Experts reverse rapidly according to a win-stay, lose-shift response pattern. We assessed whether a change in the relative control of choice by habit and working memory accounts for the development of serial reversal learning expertise. Across three experiments, we applied manipulations intended to attenuate the contribution of working memory but leave the contribution of habit intact. We contrasted performance following long and short intervals in Experiments 1 and 2, and we interposed a competing cognitive load between trials in Experiment 3. These manipulations slowed the acquisition of reversals in expert subjects, but not naïve subjects, indicating that serial reversal learning expertise is facilitated by a shift in the control of choice from passively acquired habit to actively maintained working memory.