In a complex medical center environment, the occupants of newly built or renovated spaces expect everything to “function almost perfectly” immediately upon occupancy and for years to come. However, the reality is usually quite different. The need to remediate initial design deficiencies or problems not noted with simulated workflows may occur. In our intensive care unit (ICU), we were very committed to both short-term and long-term enhancements to improve the built and technological environments in order to correct design flaws and modernize the space to extend its operational life way beyond a decade. In this case study, we present all the improvements and their background in our 20-bed, adult medical-surgical ICU. This ICU was the recipient of the Society of Critical Care Medicine’s 2009 ICU Design Award Citation. Our discussion addresses redesign and repurposing of ICU and support spaces to accommodate expanding clinical or entirely new programs, new regulations and mandates; upgrading of new technologies and informatics platforms; introducing new design initiatives; and addressing wear and tear and gaps in security and disaster management. These initiatives were all implemented while our ICU remained fully operational. Proposals that could not be implemented are also discussed. We believe this case study describing our experiences and real-life approaches to analyzing and solving challenges in a dynamic environment may offer great value to architects, designers, critical care providers, and hospital administrators whether they are involved in initial ICU design or participate in long-term ICU redesign or modernization.