A system and method of intelligently recommending items based on social media communications are provided. A communication in a first format is intercepted from a first service. An intent to transact is then detected within the communication. A recommendation engine can then be used to identify one or more items available at an ecommerce service, the one or more items related to the intent to transact within the communication. Then a reply communication can be posted to the first service in the first format, with the reply communication including the one or more identified items.