A computer implemented method for automatic, content based potential e-mail recipient determination, the method comprises the steps of comparing, by a sender, application plugin, the content of an e-mail being written by a user with keywords listed in as entries in a database, wherein the keywords are correlated with at least one e-mail address; and presenting, if at least part of the content of the e-mail matches with at least one keyword in the database, the e-mail address associated with the at least one keyword for selection as e-mail recipient to the user. An according system for automatic, content based potential e-mail recipient determination is disclosed.