Under the ordinance on littering and non-smoking in Yokohama city, smoking is not allowed in the “No-smoking areas” designated 8 areas in the city to maintain pleasant urban environments. Even strict conditions for smokers, complaints and requests regarding butts and violation on the ordinance still have been claimed. In this case study, we analysis the complaints and requests which were received bureau of civic affairs using methods of text mining. Then we conducted interview with the department of community environment which is in charge of outdoor smoking. In the consequence, we could suggest two gaps. One is requests from residents and the city’s countermeasures for outdoor smoking, and other is recognition gaps between residents and the city. To challenge such a cross organizational issue, the collaboration of the administration and communities might be effective for coexistence among various residents.