A system and method are provided for obtaining data that could affect event details, such that this data can be used to generate alerts that are sent early enough to give the user time to reach the event, predict lateness, arrange replacements/delegates, reschedule, cancel meetings in advance, etc. By more intelligently providing reminders to the user, the above-described unforeseen circumstances can be dealt with. In some embodiments, an aggregation of various external data sources as well as internal data can be used to better predict when a user should be reminded of the time for their event, determine and advise whether they may be late regardless, and/or enable the user to arrange a delegate or replacement or to reschedule or cancel the event.