Software engineering (SE) requires developers to collaborate with stakeholders, and understanding their emotions and perspectives is often vital. Empathy is a concept characterising a person’s ability to understand and share the feelings of another. However, empathy continues to be an under-researched human aspect in SE. We studied how empathy is practised between developers and end users using a mixed methods case study. We used an empathy test, observations and interviews to collect data, and socio–technical grounded theory and descriptive statistics to analyse data. We identified the nature of awareness required to trigger empathy and enablers of empathy. We discovered barriers to empathy and a set of potential strategies to overcome these barriers. We report insights on emerging relationships and present a set of recommendations and potential future works on empathy and SE for software practitioners and SE researchers.