Not all repeat purchases are created equal. They can be driven by both positive reaction toward a brand (i.e., attitudinal loyalty) and automaticity triggered by non-brand-related contextual cues (i.e., habit). Combining the loyalty literature with recent habit research, the authors suggest ways to distinguish the two drivers of repeat purchase and examine how they affect consumer response to cross-selling promotions. In Study 1, the authors propose a method to derive individual-level habit strength from consumer transaction records and demonstrate the influence of both attitudinal loyalty and habit on repeat purchase. Studies 2a and 2b then show that attitudinal loyalty facilitates cross-selling, whereas habit has the opposite effect. Finally, in Study 3, the authors suggest a specific promotional design that works better for habitual consumers than those with attitudinal loyalty and demonstrate that ignoring these two underlying drivers can lead to unintended negative consequences on consumer behavior. This research adds to a richer understanding of repatronage and yields important managerial insights into more effective cross-selling to repeat customers.