Outlook Asks for Permission frequently?

Maybe your Virus scanner is not uptodate or Outlook thinks it is invalid, see also the following info:

http://office.microsoft.com/en-us/outlook-help/i-get-warnings-about-a-program-accessing-e-mail-address-information-or-sending-e-mail-on-my-behalf-HA001229943.aspx

You have to assure, that programmatic access is allowed by Outlook and that your Virus status is valid in Outlook, then this warning doesn't popup.