A method may include receiving an instruction to communicate with a second computing device associated with a contact of a user of the first computing device, identifying one or more contact methods associated with communicating with the contact, identifying one or more communication capabilities associated with the second computing device, identifying unique pairs of contact methods and communication capabilities, selecting one or more unique pairs associated with a likelihood of reaching the contact via the associated contact method and, for each of the selected unique pairs, determining a cost associated with initiating communication to the identified contact method using the identified communication capability, and determining a reliability measure associated with the communication capability. The method may include identifying a recommended unique pair based on at least the cost and the reliability measure, and initiating communication with the second computing device to the identified contact method using the recommended communication capability.