This essay explores current environmental problems within the context of the digital age. By using several studios and elective works in MS.AAD program at Cornell as case studies, the essay connects environmental issues in urban and building scales to innovative strategies supported by emerging digital tools. The topics include scenic site water pollution, metropolitan electricity system transformation, sea level rising and flooding mitigation, water treatment, adaptive material reuse, sustainable timber customization, and urban evacuation plans.For each topic, the essay evaluates optimal design strategies through robust research and analysis. By implementing digital technologies like immersive animation engines, 3D printing, robotic arm fabrication, and interactive infographics, the projects tend to explore new territories of sustainable thinking in the architecture industry. Here, solving or mitigating environmental problems is not the only valuable sustainable design practice. Building awareness of hidden pollution is sustainable thinking. Encouraging people to play a role in the energy system through virtual games is sustainable thinking. Digitally modeling carbon footprint in building assembling and disassembling processes is sustainable thinking. Utilizing renewable natural building materials in digital fabrication is sustainable thinking. Even providing critical information about security and food services is sustainable thinking. With speculative graphic representation and small-scale fabrication prototypes, the essay bridges these innovative perceptions of sustainable design with the current digital context. It not only wants to challenge our status quo on sustainability but also aims to transform our understanding of digital technologies. If the first industrial revolution started the chapter of serving climate and environmental change, can we, with the help of the new technology revolution, mitigate or even alter the problems? Following the case study, are eight studio and elective projects the author worked on in her MSAAD program. More detailed documentation and explanations for each case study can be found in this section. A few of the projects also concern with sustainable design and development but are not selected due to a more conventional design approach.