Cimicomorpha is one of the most diverse groups in true bugs comprising more than 20,000 species, which attract a great attention for a variety of life-history strategies as well as for agricultural and medical aspects as followed: traumatic insemination in the bed bugs and their relatives (Cimicoidea), diverse feedinghabits in the plant bugs (Miridae), parasitism and blood-feeding in the bed bugs and their relatives (Cimicidae and Polyctenidae), agricultural pests in the lace bugs and the plant bugs (Tingidae and Miridae), biological control agents in the minute pirate bugs and the plant bugs (e.g., the genus Orius), disease transmission in the Triatominae (Reduviidae), and micro-habitat transitions in the assassin bugs and the flower bugs (Reduviidae and Anthocoridae). In this talk, I conducted the phylogenetic analyses of the Cimicomorpha based on the molecular data. Additionally, through the phylogenetic comparative analyses, I also present the evolutionary history of the specialized biological traits of the Cimicomorpha.