The current research proposes that order of entry moderates the impact of fit on brand extension evaluation. We conceptualize a model in which new brands enter the market dynamically, driving consumers to engage in differential processing as a function of pioneer and follower evaluation scenarios. We posit that consumers rely on singular evaluative processing in pioneer contexts and comparative evaluation in follower contexts, producing unique moderating effects based on the existence of comparison brands. Experimental results indicate that follower brands can actually benefit from comparison with pioneering brands that have a relatively lower fit with the extension category.