We delve into the recent turmoil surrounding two major players in the tech world. First, we explore the widespread Microsoft 365 outages that left thousands of users without access to critical tools like email and Teams. Then, we turn our focus to Canva, where a staggering 400%+ price hike for Teams plans has sparked outrage among users. As Canva doubles down on AI, we question whether this aggressive pricing strategy will alienate its core user base. With a broader discussion on the risks of subscription-based models and the potential for these platforms to hold users' work hostage.