Meiosis is a specialized type of cell division that is crucial for the sexual reproduction of all eukaryotes. This process entails unique cellular events such as meiotic recombination and a double round of chromosome segregation, which are tightly coordinated at the molecular level. Furthermore, in plants, meiocyte development relies on tissue and organismal cues that synchronize the cell cycle between individual cells and orchestrate gamete development between the sexes. In contrast to meiosis in animal species, plant meiosis is remarkably plastic and responds to environmental stimuli, such as temperature. In this review, we provide an overview of the known mechanisms that control meiotic progression in plants. This includes the regulation of gene expression at the transcriptional, post-transcriptional, and post-translational levels and communication between meiocytes and the surrounding somatic tissue. We conclude with examples of biotechnological applications of manipulating meiotic progression and the effects of environmental stress on meiotic events, allowing for the engineering of meiotic events for the benefit of plant breeding.