Artificial Intelligence seems o rather is at the centre of recent technological developments. It has certainly disrupted the way we work, how services are provided, and how businesses operate. Corporate governance has not been immune to this phenomenon, in fact, to maximise efficiency and outputs, companies have gradually introduced machine learning, reinforcement learning and deep neural networks, into their entire structures and it was a matter of time before the corporate legal framework would reach a checkpoint. More recently, the market has seen the appointment of robo-directors to predict market fluctuations and identify business opportunities which in one way or another triggered the amalgamation of existing directorial duties with their robotic counterparts. Such adaptation poses the difficult task of applying subjective test to ascertain some of directors’ liabilities, to robo-directors whose decisions can only be objectively assessed. The black box problem impedes us to know why a decision was made in the way it was made. This piece of research aims at speculating with some ideas as to how existing directorial duties could be adapted to the current robotic challenges. Additionally, the D&O insurance market cannot remain static and need to equally adapt to the circumstances yet the problem it faces is that its existing Side A and B wordings may not be suitable for robo-directors. Whether or not robots’ personhood will be recognised is a matter of time, for the time being, it seems that Side C or Corporate Entity cover appears to be the most effective way to protect corporate bodies when using robots, to make decisions. The “Question can, and should robots have rights consists of two separate queries: ‘can robots have rights?’ Which is a question that asks about the ontological capabilities of a particular entity; and ‘should robots have rights? Which is a question that inquiries about normative obligations in the face of this entity. These two questions invoke and operationalized a rather famous distinction in philosophy that is called the is/ought problem, or Hume’s Guillotine”. David Gunkel (Gunkel, Robot rights, 2018, p. 2).