The article contains the author’s generalization of the available research data for the purpose of sociological representation of the urban environment comfort and design tools for its development. The subject of the study is presented as a parameter of socio-spatial development and as a task, the importance of which is articulated at the state level and has its own regulatory, documentary and expert confi rmation. The study used methods of content analysis and expert online interviewing of a semi-formalized type. The comfort parameter is shown through a number of target and instrumental components; the conditions for its development are highlighted. Expertly formulated important principles for the development of a comfortable urban environment are as follows: striving for a social balance of interests of the subjects involved; ensuring trust between them; development of the human potential of the city. Digitalization itself and the Smart City concept in particular are neutral tools; their nature and eff ectiveness depend on what tasks they solve, how they fi t into the specifi cs of certain spaces. A number of related factors and implementation risks are formulated with reference to a specifi c case; its representativeness to the declared topic is shown. Possible directions for further eff orts to address them are noted.