This paper examines the relationship between extension difficulty, defined as the perceived difficulty of manufacturing the extension product, and attitudes toward brand extensions. Although extant literature has hitherto modeled this relationship as a simple monotonic relationship, a study by Bottomley and Holden (Journal of Marketing Research, 38(4):494-500, 2001) has questioned its empirical generalizability. We suggest that the relationship between extension difficulty and extension attitudes may be far more complex than a simple linear relationship. Based on theoretical evidence drawn from the concept of evaluation difficulty, we suggest that the relationship between extension difficulty and extension attitudes is best modeled as a curvilinear (inverted U-shaped) relationship. Further, we explore the specific role of perceived transferability as a moderator of this curvilinear relationship.Empirical tests conducted using two studies provide support for both the theoretical mechanism and the proposed hypotheses. Entry into "easy" or "extremely difficult" extension categories carries its own penalties while entry into "moderately difficult" categories appears to garner high consumer attitudes for brand extensions.