From a perspective of safeguarding Intangible Cultural Heritage, this paper discusses how to enhance the appreciation of traditional Chinese painting through the support of interactive technology. The author analyses extensive yet current case studies based on the findings from the interactive appreciation of and engagement with paintings. The author then summarises four aspects of how to design interactive technology in order to support the appreciation of and engagement with traditional Chinese paintings: (1) deepening the aesthetic understanding of traditional Chinese paintings should not be a neglected aspect during the design process; (2) current case studies have not considered distinguishing the user experience between professional artists and amateurs (who are unskilled at painting); (3) it is vital to exploit interactive technology to improve the originality and subtlety of traditional Chinese painting; and (4) employing interactive systems to engage users in participatory appreciation (through encouraging them to talk about art or discussing their understanding of it) could provide potential design insights for future studies.