Apple is one of the most important economic fruit crops in the world. Despite all the strategies of integrated pest management (IPM), insecticides are still frequently used in its cultivation. In addition, pest phenology is extremely influenced by changing climatic conditions. The frequent spread of invasive species, unexpected pest outbreaks, and the development of additional generations are some of the problems posed by climate change. The adopted strategies of IPM therefore need to be changed as do the current monitoring techniques, which are increasingly unreliable and outdated. The need for more sophisticated, accurate, and efficient monitoring techniques is leading to increasing development of automated pest monitoring systems. In this paper, we summarize the automatic methods (image analysis systems, smart traps, sensors, decision support systems, etc.) used to monitor the major pest in apple production (Cydia pomonella L.) and other important apple pests (Leucoptera maifoliella Costa, Grapholita molesta Busck, Halyomorpha halys Stål, and fruit flies—Tephritidae and Drosophilidae) to improve sustainable pest management under frequently changing climatic conditions.