Open Outlook and in your mailbox open the Rules menu from the Mail ribbon (or right click on a mail message). This article has been build with screenshots of Office 2016 (O365), but you can apply the same principle to previous versions. Original / partial solution on MSDN Blog by Jezz Santos: Where Jezz stops, this article continues and provides you with a step by step guide to get it configured, including an exception to allow you sending mails immediately, when you explicitly do not want to have a delay. and Jezz hinted to a solution with a mail rule. (see theīut this solution has some distinct disadvantages. The topic has been discussed before offering a solution by setting the delay manually. In Outlook there is a very simple trick to give you enough time to delay the mail, just in case you change your mind. While using email, probably everyone recognizes the 'oh sh*t' moment, hitting the send mail button, and immediately regretting sending it. This might break future edits of the article. Due to some key word filtering, that protects the TechNet Wiki, the most important key word has been masked.