The importance of high initial smoothness on newly constructed or rehabilitated pavement facilities has been identified by many researchers and recognized by many road agencies. Pavements with high initial smoothness display retarded roughness progression and, therefore, longer service lives. In Ontario, Canada, the Ministry of Transportation (MTO) implemented a bonus/penalty system for smoothness in the mid-1990s. Initially based on the profile index and scallops (i.e., bumps) measured with a California Profilograph, the specification is now based on the International Roughness Index analyzed locally (for bumps) and over regular intervals. The potential bonus for high initial smoothness in Ontario is considerable, as is the potential penalty for excessive roughness. Furthermore, the ability to correct areas of excessive roughness after placement is greatly limited by the MTO because the public does not wish to observe a new pavement surface being “damaged” by a milling machine. Given such, contractors are proactively requesting smoothness testing on base pavement layers so that areas of excessive roughness can be addressed prior to the placement of the surface layer. However, once the smoothness of the base layer is determined, the contractor must decide whether areas of excessive roughness will be sufficiently smoothed by the surface hot mix asphalt (HMA) layer or whether milling is first required (at additional cost). In addition to a brief overview of the Ontario smoothness specification, this paper presents the change in pavement smoothness with increasing HMA layers measured at a select project location in order to identify how much additional smoothing a contractor should anticipate. Of particular interest is the change in smoothness from an in-place recycled layer to a base HMA layer and, finally, a surface HMA layer. The results will allow contractors to optimize pavement smoothness (and their associated bonus) while minimizing costly corrective milling.