The paper presents the general conditions in which the pastoral work of mendicant orders was conducted in the domains of the Teutonic Order and particular bishoprics in Prussia and Livonia, at the same time indicating similarities and differences in the situations in which friars had to work in these areas. The research focuses exclusively on pastoral work conducted among the urban population. The network of mendicant friaries in Prussia and Livonia was a reflection of the demographic potential and the degree of urbanisation of both parts of the domains of the Teutonic Order. The scale of effectiveness of the friars is authenticated by numerous references to prayer agreements concluded with members of religious orders and guilds of craftsmen, burials in friary churches (tombstones), and bequests of townspeople. The degree of success of mendicant orders and the support of the townspeople is confirmed in the partially preserved great hall-type churches erected by mendicants in the main towns (Gdańsk, Toruń, Tallinn, Riga).