Technological advances such as the Internet-of-Things, big data, and artificial intelligence have enabled new ways of managerial oversight moving away from panoptic surveillance to what we call “connected surveillance”. The COVID-19 pandemic has accelerated the adoption of connected surveillance which purpose is not only scruitizing employees’ work performance but also health, personal beliefs, and other private matters. With the implementation of connected workplaces, therefore, various ethical dilemmas arise. We highlight four emerging dilemmas, namely: (1) the good of the individual versus the good of the community, (2) ownership versus information disclosure, (3) justice versus mercy, and (4) truth versus loyalty. We discuss those ethical dilemmas for the case of corporate wellness programs which is frequently used as guise to introduce connected surveillance. Following a socio-technical perspective, we discuss ethical responses that focus on people involvement and technology assessment. We also highlight practical responses that can aim at mitigating the dilemmas.