With the COVID 19 pandemic forcing the majority of the world to stay indoors over the last year, demand for in home entertainment such as video games has grown immensely. While this has led to some incredibly positive outcomes for the gaming industry, namely profit and recognition, it has also uncovered some of the problems in the development and distribution of video games. In March and April of this year, the issue of game preservation made major headlines when Sony announced it would shut down the online store for its older PlayStation 3 and PlayStation Portable systems. This decision and the discourse it spawned inadvertently placed a spotlight on the problem of how companies can control the lifespan of digital media such as video games. As Taiwanese video games like Detention, Devotion, and Carto are finally pushing Taiwanese popular culture onto the world stage, it is of utmost importance to ensure we can preserve this kind of digital heritage for future generations to appreciate. Using case studies from research done while working with Taiwanese video games, this paper aims to explore the challenges that hinder the proper preservation of video games and other digital media. From this investigation, some of the major issues uncovered in preserving video games include digital rights management software, operating system fragmentation, firmware incompatibility, region locking, hardware obsolescence, and digital storefront availability. A final challenge unique to Taiwanese video game preservation, is related to politics, namely the influential power that Chinese netizens, companies, and the CCP itself have over Taiwanese game sales and distribution. Each of these issues affects preservation in a different way and different approaches are needed to find viable solutions. While it would be ideal that game developers and publishers would hold the biggest responsibility for solving these problems, many solutions end up coming from fan communities even though they have far fewer tools at their disposal. Throughout this paper many problems and solutions are discussed on a consumer-impacting level, while also highlighting how the technological friction caused by the entire process can alter one's experience of the game they want to play. This friction, which on the surface may merely seem inconvenient today, can actually have major ramifications for future researchers. By showcasing the entire process involved in getting several different Taiwanese video games running on modern devices, this paper demonstrates that not only are many of the problems plaguing digital media preservation avoidable, but also that these problems could be responsible for altering future players' access to the works. As the world continues to become more and more online and our digital media landscape continues to grow, it is of the utmost importance that more work needs to be done to ensure that the process for future digital media preservation be streamlined as soon as possible.