How do we manage software with care? We live in a world where resources are scarce and new resource-intensive projects have the potential to take over a team's workload. Balancing new projects alongside the day-to-day business of migrations, upgrades, and security fixes become a Herculean task. The dedication and energy invested in the phases of the software life-cycle leading to a launch often leave little resources for the maintenance phase. This in spite of the fact that this phase is likely to be the longest and most labor-intensive over the course of a system's life. How do libraries reconcile the excitement and dedication that goes into launching a system, with the less glamorous, but necessary maintenance of it thereafter? With administrators and patrons desiring new systems, how can we give proper care to those already in existence? What rewards do we give for the (sometimes) invisible labor that goes into sustaining these systems? In this presentation, we will talk about a generalized problem in library technology: how do we convey the value of the maintenance phase and how do we care for the systems we create?