Techniques are disclosed for initiating an electronic file transfer between users based on conversational context. A cognitive service monitors a communication between a given user and another user. The communication is exchanged by a mobile device associated with the given user and a mobile device of the other user. The cognitive service determines a context of the communication. The cognitive service detects, based on the context of the communication, a request between the users to share a file maintained by the given user. Upon successfully validating the request, a transfer of the file to the second user is performed.