In addition to saliency and goal-based factors, a scene’s semantic content has been shown to guide attention in visual search tasks. Here, we ask if this rapidly available guidance signal can be leveraged to learn new attentional strategies. In a variant of the scene preview paradigm (Castelhano & Heaven, 2010), participants searched for targets embedded in real-world scenes with target locations linked to scene gist. We found that activating gist with scene previews significantly increased search efficiency over time in a manner consistent with formal theories of skill acquisition. We combine VGG16 and EBRW to provide a biologically inspired account of the gist preview advantage and its effects on learning in gist-guided attention. Preliminary model results suggest that, when preview information is useful, stimulus features may amplify the similarities and differences between exemplars.