A vehicle monitoring apparatus includes: a first communicator that receives specifying information for specifying a target vehicle from a server; and an acquirer that acquires driving information from the target vehicle, the driving information being information regarding driving of the target vehicle specified by the specifying information received by the first communicator. The first communicator transmits the driving information acquired by the acquirer to the server. For example, the acquirer may acquire the driving information obtained from the target vehicle through communication.