The present disclosure describes systems and methods for using for a simulated phishing campaign, information about one or more situations of a user determined from an electronic calendar of the user. A campaign controller may identify an electronic calendar of a user for which to direct a simulated phishing campaign, determine one or more situations of the user from information stored in the electronic calendar and select either a template from a plurality of templates or a starting action from a plurality of starting actions for the simulated phishing campaign based at least on the one or more situations of the user. The campaign controller may communicate to one or more devices of the user a simulated phishing communication based at least on the respective template or starting action.