We are processing many photographs on a daily basis, but our understanding of perceptual and aesthetic processing of photography is limited. The relationship between processing fluency and aesthetic evaluations was studied in a varied set of high-quality artistic photographs. Interactions between subject matter (e.g., portrait), medium (e.g., sharpness, color, portrait orientation), and form (e.g., filling of the frame, uniform background, vertical symmetry) appeared to be relevant for evaluated fluency of processing. The pleasure-interest model of aesthetic liking (Graf & Landwehr, 2015) was tested on a selection of low, medium, and high-fluency photographs. Results were partly in line with the model, showing two routes to aesthetic liking with different relationships to fluency. In the automatic condition, high-fluency photographs were found most pleasant, but in the controlled condition, low-fluency photographs were found most pleasant. Regarding interest, however, all conditions showed the highest interest for the low-fluency photographs, irrespective of processing style. We therefore explored the relationship between fluency and interest for larger sets of photographs (heterogeneous and homogeneous in subject matter), finding similar low interest percentages for the highest fluency photographs, but here the highest interest ratings were found for medium levels of fluency. In general, the studies show that investigating how processing fluency relates to aesthetic impressions of photographs can be a promising but complex avenue. Data and analyses code can be found at: https://osf.io/b3z2y/.