There is a need for solutions that monitor memory loss with reduced caretaker involvement. This need can be addressed by, for example, selecting a first question from a group of multiple questions to ask a user of a computing device based one or more attributes associated with each question in the group of multiple questions; receiving a first answer by the user of the computing device to the first question; determining, from the first answer, one or more behavioral attributes associated with user response to the first question; and determining, based on the one or more behavioral attributes, a cognitive capability of the user of the computing device.