Creating an attractive cityscape has become one of the most promising actions to improve urban functionality and increase urban competitiveness. However, the resistances from the local inhabitants are always against the urban development. Taipei City, a metropolis in Taiwan, is now composed of complex urban systems chaotically enclosed by existing and new urban environments. The city government is attempting to re-shape its cityscape by implementing a series of city regeneration plans, namely "Taipei Beautiful", considering the improvement of urban landscape, greenery open space, built environment, sustainable campuses and public facilities. These actions represent how Taipei city government educates its citizens toward to identify and recognize the benefits from the developments. Although Taipei Beautiful is an ongoing project, achievements of the current stage have revealed potentials to significantly increase the number of tourists, decrease energy consumption, and promote economic benefits. This study presents an overall review of educational strategies and actions enacted by the city government. Difficulties, challenges, and the role of the city government in affecting inhabitants' identification and recognition are also discussed. Lessons learned in Taipei City could be useful for other cities that are facing similar city development requirements.