While commercial possibilities of emotional AI for businesses are manifold, so are the risks this technology brings. Currently, debate on legal and ethical aspects in the area of commercial emotional AI is ongoing and even a ban is being considered, potentially endangering innovation and the commercial uptake of emotional AI in the EU. It is safe to say that the provision of this technology takes place in a grey area at the moment, causing particular attention to legal and ethical dilemmas. This chapter is an explorative study about collision, dependency and compatibility of law, ethicsEthics and practice in the area of commercialization of certain type of emotional AI—emotion-aware systems at workplaces. If the processing of emotions—one’s own and others’—by people is already complex and at times risky, how can a company utilize emotional AI commercially in both a legally and ethically responsible manner? Firstly, this chapter explores how the relevant legislation in terms of AI balances the risks and possibilities of emotional AI. Following this, the chapter explores how a company can navigate in practice through the current obstacles in its way to the provision of lawful and responsible emotional AI services.