When children with ADHD are presented with behavioral choices, they struggle more than Typically Developing [TD] children to take into account contextual information necessary for making adaptive choices. The challenge presented by this type of behavioral decision making can be operationalized as a Conditional Discrimination Learning [CDL] task. We previously showed that CDL is impaired in children with ADHD. The present study explores whether this impairment can be remediated by increasing reward for correct responding or by reinforcing correct conditional choice behavior with situationally specific outcomes (Differential Outcomes). An arbitrary Delayed Matching-To-Sample [aDMTS] procedure was used, in which children had to learn to select the correct response given the sample stimulus presented (CDL). We compared children with ADHD (N = 45) and TD children (N = 49) on a baseline aDMTS task and sequentially adapted the aDMTS task so that correct choice behavior was rewarded with a more potent reinforcer (reward manipulation) or with sample-specific (and hence response-specific) reinforcers (Differential Outcomes manipulation). At baseline, children with ADHD performed significantly worse than TD children. Both manipulations (reward optimization and Differential Outcomes) improved performance in the ADHD group, resulting in a similar level of performance to the TD group. Increasing the reward value or the response-specificity of reinforcement enhances Conditional Discrimination Learning in children with ADHD. These behavioral techniques may be effective in promoting the learning of adaptive behavioral choices in children with ADHD.