The interest in re-implementing agroforestry (AF) in European agriculture due to its environmental benefits has been growing exponentially. We reviewed the historical background and the current state (extent, farmers’ perception, legislative support, and barriers) to evaluate the future perspectives of AF in Czechia by identifying the key factors hampering further extension. Our results confirmed that AF almost disappeared after the middle of the 19th century due to agricultural intensification and collectivization. Currently, AF is not defined in the Czech legislation and no modern AF has been encountered by this study. Areas falling into AF definition recently comprise only traditional AF (less than 1% of agricultural area remaining) represented only by silvopastoral AF. The results of a farmers’ survey indicated that despite relatively high interest in AF, excessive bureaucratization, high costs of establishment and uncertain profitability are severe concerns among farmers. We therefore conclude that there is a lack of legal recognition and marginalization of AF as the key obstacles of low adoption rates. We suggest that systematic support beyond subsidies should include raising awareness, research, policy, legislation changes, training, and advisory service, as a cornerstone for progressive development of AF and thus conservation and creation of economically and environmentally sound landscapes throughout Czechia.