An information processing apparatus according to an embodiment of the present technology includes an assessment unit and a setting unit. The assessment unit performs weighting on an examination item relating to an examination with an ophthalmic microscope on the basis of medical information relating to a patient. The setting unit sets an operation relating to the examination with the ophthalmic microscope on the basis of the weighting of the examination item. Accordingly, the usability of the ophthalmic microscope can be improved.