This talk will aim to briefly address how a DevOps Engineer recommends analyzing and dealing technical debt (with the use of real life use cases) and then on the flip side, provide the take on how a project manager addresses dealing with technical debt. Technical debt can refer to many different things including, but not limited to: infrastructure, software, design/UX, documentation or code. I want to note that inevitably we will always take on some sort of technical debt, debt that we create, often unknowingly and usually while learning and working on a new project and debt that we’ve inherited. Technical debt, when taken on haphazardly and not managed, can shut down a team’s ability to move forward on a project. It is important to have ways of hammering through it, as well as having preventative measures in place to keep debt to a minimum and manageable for as long as possible. The decisions that are made which result in technical debt should be made with a strategic engineering perspective. Addressing technical debt from a DevOps point-of-view and a Managerial point-of-view can have significantly different perspectives of the impact and detriment of technical debt, affecting when, how and what technical debt should be addressed and dealt with.