Solution 1:

Have a look at OLKeeper

alt text

Solution 2:

Edit years later:

Using KeepOutlookRunning mentioned in the duplicate question: https://superuser.com/a/275244/49695

Original:

Finally figured out a working solution that doesn't involve installing something I have to pay for... I've been trying to figure this one out for weeks before I really put too much time into it today:

Powershell script:

# Start outlook if not running
Clear-Host

if (Get-Process "OUTLOOK") 
{

}
else 
{ 
    Invoke-Item "C:\Program Files\Microsoft Office\Office14\OUTLOOK.EXE" 
}

Setup a task scheduler that runs every 5 minutes. If outlook is found, empty part is run... else, Invoke-Item runs Outlook.

To enable running of Powershell Scripts... Enable running of locally created scripts (foreign scripts must be signed by a trusted source):

run Powershell as administrator  
Set-ExecutionPolicy RemoteSigned  

Bam. I know I'm not the one with this problem... and don't wish to spend $60 on a solution for something so simple. I'm not cheap, but I'd rather spend that money on my girlfriend :)