Regarding cross-modality research, taste-aroma interaction is one of the most studied areas of research. Some studies have reported enhancement of sweetness by aroma, although it is unclear as to whether these effects actually occur: depending on the cognitive strategy employed by panelists, the effects may disappear, e.g., forcing panelists into an analytical strategy to control for dumping may not be able to reveal perceptual interactions. Previous studies have largely focused on solutions and model foods, and did not test stimuli or concentrations relevant to real food applications. This study addresses these gaps: 18 vanilla flavored sucrose milks, varying between 0–0.75% (w/w) two-fold vanilla, and 0–5% (w/w) sucrose, were rated by 108 panelists for liking and perceived sweetness, vanilla flavor, milk flavor, and thickness. Interactions between vanilla and sucrose were measured using deviations of real mixtures from additive models (via the isobole method), indicating vanilla aroma does enhance perceived sweetness. However, the sweetness enhancing effect of vanilla aroma was not as pronounced as that of sucrose on vanilla flavor. Measurable cross-modal interactions occur despite using an analytical cognitive strategy. More work is needed to investigate the influence of perceptual strategy on the degree of taste-aroma interactions in real foods.