An electronic mail client includes features for preventing addressing errors in electronic messaging such as those caused by predictive text features. A messaging client tracks addressing parameters including the length of time since each previous addressee has been messaged, the quantity of times selected addressees have been co-addressees on messages, if any, whether the addressees are designated as sensitive and whether the messages contain sensitive subject matter. If a high risk of addressing error is determined, the client delays transmission of the message to permit the user to review the message recipient addresses and correct any erroneous addressees.