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Simple Summary: In everchanging landscapes with intense land use for agriculture, forestry and settlements, songbirds need to adapt their feeding and breeding behaviour according to changing habitats and food supplies. Blue and Great Tits occur in various habitats from forest to park-like sites and strongly rely on caterpillars to feed their offspring. Using genetic analyses of Blue and Great Tit droppings, we compared the diet composition of nestlings among forest, urban parks, and meadows with scattered fruit trees (traditional orchards). Additionally, we compared the food availability in the trees of each habitat to the respective nestling diets. Both bird species showed a diverse diet dominated by butterflies in all habitats. Moth components in the diet were most similar between forest and orchard sites, while components of other insect-like prey were most similar between orchard and urban sites. Both bird species especially selected three major moth families at all sites and alongside two families of sawflies in the orchard and forest sites. Our results on nestling diet and prey preferences provide further insights in the feeding behaviours of Blue and Great Tits among changing anthropogenic landscapes. Moreover, our genetic approach using bird droppings provides a baseline to support insect monitoring. Increasing landscape transformations and urbanisation affect insectivorous bird populations in various ways such as food availability, breeding phenology, or reproductive success. Especially during the breeding season, many passerine birds rely on the availability of caterpillars as the main prey for their nestlings. Previous studies suggested that similar diet preferences of sympatric species may result in interspecific competition, as demonstrated for Blue and Great Tits in forest habitats. However, nestling diet and prey preferences in other habitats are not fully understood. Prey availability, especially caterpillars, is lower in cities than in forests, thus influencing prey choice and interspecific competition. Here we used faecal DNA metabarcoding to investigate if nestling diet composition of the two sympatric species Blue Cyanistes caeruleus and Great Tits Parus major varied among species and different habitats (forest, traditional orchards, and urban parks). Furthermore, we examined food availability by DNA barcoding of the arboreal arthropod communities among habitats and compared them to the nestling diet to infer parental prey selectivity. The study was carried out in central Germany from 2018 to 2019. Blue and Great Tits showed a diverse diet which was dominated by Lepidoptera in all habitats. Lepidopteran diet components were most similar between forest and orchard sites, as were the components with other arthropods between orchard and urban sites. Both tit species showed selectivity for the lepidopteran families Geometridae and Tortricidae in all habitats, and for Noctuidae (Lepidoptera), Tenthredinidae and Braconidae (Hymenoptera) in forest and orchard sites. As the tits showed preferences for mainly families of Lepidoptera, and Hymenoptera, our approach provides a baseline to support monitoring of these groups. [ABSTRACT FROM AUTHOR]