There is provided an information processing apparatus to reduce the burden of label assignment and achieve learning that is more flexible, the information processing apparatus including: a learning unit configured to perform machine learning using training data to which a constraint label is assigned. The constraint label is a label in which a type of constraint that a normal label is to follow is defined. In addition, there is provided an information processing method including: performing, by a processor, machine learning using training data to which a constraint label is assigned. The constraint label is a label in which a type of constraint that a normal label is to follow is defined.