People often use tools for tasks, and sometimes there is uncertainty about whether a given task can be completed with a given tool. This project explored whether, when, and how people’s optimism about successfully completing a task with a given tool is affected by the contextual salience of a better or worse tool. In six studies, participants were faced with novel tasks. For each task, they were assigned a tool but also exposed to a comparison tool that was better or worse in utility (or sometimes similar in utility). In some studies, the tool comparisons were essentially social comparisons, because the tool was assigned to another person. In other studies, the tool comparisons were merely counterfactual rather than social. The studies revealed contrast effects on optimism, and the effect worked in both directions. That is, worse comparison tools boosted optimism and better tools depressed optimism. The contrast effects were observed regardless of the general type of comparison (e.g., social, counterfactual). The comparisons also influenced discrete decisions about which task to attempt (for a prize), which is an important finding for ruling out superficial scaling explanations for the contrast effects. It appears that people fail to exclude irrelevant tool-comparison information from consideration when assessing their likelihood of success on a task, resulting in biased optimism and decisions.