A method of automatically communicating personalized messages to a telematics-equipped vehicle includes the following steps: (a) creating a personalized message; (b) defining playback instructions for playing the personalized message; (c) generating a trigger based on the defined playback instructions; (d) setting the trigger; (e) monitoring for the occurrence of one or more conditions that satisfy the trigger; and (f) determining that the one or more conditions have occurred and, if so, then; (g) accessing the personalized message associated with the trigger; and (h) playing the personalized message.