Monday, October 18, 2010

Outlook Annoyance - A program is trying to automatically send e-mail on your behalf...

Have you ever attempted to send an email from another program (Other than Outlook) but have Outlook send out the email? If you do then chances are you ran into the annoying prompt below...

This is a "security" feature of Outlook in an attempt to warn you that a third party application is attempting to send out email via Outlook. I see this as more of an annoyance than security. When searching the Microsoft KB on how to disable this, I came up blank because the only way is to turn it off on your Exchange server side. So how many people run an Exchange server in their own home for personal email? I didn't think I would get too many yeses. 

Luckily I found a pretty neat utility that will automatically answer Yes to the annoying prompts. It not only click Yes for you but it will bypass the counter (time you need to wait before that Yes button become available for you to click). Just head over to Context Magic ( and look for a program call ClickYes. They offer a free and paid version, the paid version will allow more flexibility, controls and support for later versions of Outlook, but if all you’re after is to get rid of that annoying prompt and you are running Outlook 2003 or older, the free version will suffice.

Installing and using the free version is straight forward...

  1. Download the free version of ClickYes.
  2. Double click on the downloaded file and follow the prompts to install.
  3. When you run ClickYes, it will appear in the notification area of your task bar with a small red x. Indicating that it is running in suspense mode. You can activate ClickYes by double clicking on it to take it out of suspense mode.
  4. With ClickYes activated, you will see the Outlook prompts pass quickly by when sending emails through Outlook from a third party application. 

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