I have not found any security setting that allows me to get past this obnoxious feature! Question: What Security setting, or other change, do I need to make in order to be able to send .exe file attachments with Emails in Outlook 2002? Thank you, WEB7   There are two approaches to this. The first is something of a bodge - change the extension, and tell the receiver to change it back to .exe. (change run.exe run run.2exe, for example). The second is more elegant, and involves trying to persuade Outlook to behave more sensibly: This web page explains a number of options to reduce the security levels in Outlook 2002: http://www.slipstick.com/outlook/esecup/getexe.htm#ol2002 Search strategy: I searched the Archives of the (very useful) Woody's Office Watch, http://www.woodyswatch.com/ . After a number of unsuccessful attempts (using words such as .exe, outlook, send, attachments), I finally used "Draconian", which did the trick. The search page is here: http://www.woodyswatch.com/office/archives.asp I hope that this leads to a solution to your problem. if not, please feel free to request clarification.