Sending attachments when you mail merge in Outlook

In my Computer Magic! seminar at the Affordable Meetings conference, several attendees wanted to know how to send an attachment when they send a mail merge email.

The bad news is that you can’t with the native Outlook program.

But, the good news is that you can purchase an inexpensive add-in ($24.00) that will make this easy (if you’re on a company network, check with your IT administrator before you attempt to download anything to your work computer).

Somewhere along the way as you start the merge, you may get a message about a program trying to send email on your behalf…You can avoid this happening by downloading the “Express ClickYes” utility that is available as a free download from

“Express ClickYes is a tiny program that sits in the taskbar and clicks the Yes button on behalf of you, when Outlook’s Security Guard opens a prompt dialog saying that a program is trying to send an email with Outlook or access its address book. You can suspend/resume it by double-clicking its taskbar icon.”