(1) Background: As COVID-19 transmission continues despite vaccination programs, healthcare workers (HCWs) face an ongoing pandemic response. We explore the effects of this on (1) Heartware, by which we refer to morale and commitment of HCWs; and identify how to improve (2) Hardware, or ways of enabling operational safety and functioning. (2) Methods: Qualitative e-diary entries were shared by HCWs during the early phases of the outbreak in Singapore from June to August 2020. Data were collected via an online survey of n = 3616 HCWs of all cadres. Nine institutions—restructured hospitals (n = 5), affiliated primary partners (n = 2) and hospices (n = 2)—participated. Applied thematic analysis was undertaken and organized according to Heartware and Hardware. Major themes are in italics (3) Results: n = 663 (18%) HCWs submitted a qualitative entry. Dominant themes undermining (1) Heartware consisted of burnout from being overworked and emotional exhaustion and at times feeling a lack of appreciation or support at work. The most common themes overriding morale breakers were a stoic acceptance to fight, adjust and hold the line, coupled with motivation from engaging leadership and supportive colleagues. The biggest barrier in (2) Hardware analysis related to sub-optimal segregation strategies within wards and designing better protocols for case detection, triage, and admissions criteria. Overall, the most cited enabler was the timely and well-planned provision of Personal Protective Equipment (PPE) for front-liners, though scope for scale-up was called for by those not considered frontline. Analysis maps internal organizational functioning to wider external public and policy-related narratives. (4) Conclusions: COVID-19 surges are becoming endemic rather than exceptional events. System elasticity needs to build on known pillars coupling improving safety and care delivery with improving HCW morale. Accordingly, a model capturing such facets of Adaptive Pandemic Response derived from our data analyses is described. HCW burnout must be urgently addressed, and health systems moved away from reactive “wartime” response configurations.