Digital transformation is expensive and rarely smooth, often leading to higher costs than anticipated. It is challenging to demonstrate the contribution of digital health investment in achieving the healthcare aims of population health and workforce sustainability. We conducted a scoping review to understand how electronic medical record (EMR) implementations in the hospital setting have been evaluated using cost–benefit analysis (CBA) approaches. The review search resulted in 1184 unique articles, a final list of 28 was collated of which 20 were US-based studies. All studies were published in 2010–2019, with fewer studies published in more recent years. The data used to estimate benefits and costs were dated from 1996 to 2016, with most data from 2000 to 2010. Only three studies were qualified as using cost–benefit analysis approaches. While studies indicated that there is a positive impact from the EMR implementation, the impacts measured varied greatly. We concluded that the current literature demonstrates a lack of appropriate and comprehensive economic frameworks to understand the value of digital hospital implementations. Additionally, most studies failed to align fully to the quadruple aims of healthcare: they focused either on cost savings and/or improved patient outcomes and population health, none investigated healthcare-workforce sustainability.