The present invention assists at work related to the setting of an evaluation index for a vehicle operation plan. A vehicle operation assistance device manages one or more pieces of evaluation information including information regarding evaluation of the vehicle operation plan, acquires setting target information that is information regarding evaluation, the information being intended to be set for the vehicle operation plan by a user, derives a similarity degree between the setting target information and each pieces of the evaluation information, extracts evaluation information on the basis of the similarity degree, receives a setting for information regarding evaluation related to the vehicle operation plan from the user while presenting similar evaluation information which is the extracted evaluation information to the user and generates evaluation information on the basis of a received content. The vehicle operation assistance device provides a user interface for visually presenting a method for calculating an evaluation index included in the similar evaluation information, in a state in which the user can edit the method.