Custom rule for Outlook 2010

Question

Sorry if this is a repeat of others but none of the ones I read meets my specific need.
I am trying to create a desktop alert to tell me that there is mail still in my Outbox. This would need some kind of adjustable timer so I could set it to pop up every minute or so as long as mail was still in my outbox. I have had a lot of problems recently where mail that I sent did not go out for whatever reason. When I close Otlook, even if I set it to do a final send on exit, sometimes the mail stays.
I acually would like to be able to prevent Outlook from closing if any mail was still in the outbox. And in any event, when I reopen it, if the same email still doesnt go out, I need to get an alert every few minutes.
This might eventually get annoying but right now the need is greater than the worry about being annoyed as several important emails have missed their deadlines because I did not know they were still stuck there. Until I can find and fix the problem, I would rather be notified as often as it takes.

Answer 1

I've written a script that might interest you. You can read about it here. Newer version of the code is on GitHub.

In the code that you will get with first link there is a function called balloon (code below). You can use this function to create a pop-up message that will show up near the tray icons. It will look like that:

If you modify the script to run every couple of minutes, and create a rule for each email that resides within your outbox folder - you will get a popup message for each of the emails that have not yet been sent.

The balloon function:

function balloon([string]$text, [string]$title)
{
    if ($objBalloon)
    {
      # DELETE EXISTING BALLOON
      $objBalloon.Dispose()
    }

    [void] [System.Reflection.Assembly]::LoadWithPartialName("System.Windows.Forms")
    $objBalloon = New-Object System.Windows.Forms.NotifyIcon
    $objBalloon.Icon = "C:\Windows\ServicePackFiles\i386\msnms.ico"

     # INFO, WARNING AND ERROR VALUES ARE ALLOWED
      $objBalloon.BalloonTipIcon = "Error"
      $objBalloon.BalloonTipTitle = "$title"
      $objBalloon.BalloonTipText = "$text"
      $objBalloon.Visible = $True

     # HOW LONG TO SHOW THE BALLOON
      $objBalloon.ShowBalloonTip(5000)
}