Hi Darren,
Thank you for posting here. I'm JohnJr and I'll help you wich this technical issue.
From your problem description, I understand when sending mails to specific users, the mails go directly to permanently deleted items. Please correct me if I've misunderstood.
It seems to me this is an account related issue. I suggest you perform following tests in order:
Step 1: Test the issue on another machine
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Please configure the problematic user's Exchange account on another machine and check whether the same issue occurs. This way, we can isolate the issue to the specific machine.
If it only occurs on the specific machine, please continue to try the following steps.
Step 2: Test in Outlook Safe Mode
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Outlook Safe Mode can narrow down issues which are caused by any extensions, corrupted resources, files, registries, or templates.
1. Click Start | Run.
2. In the Open box, type: "Outlook /safe" (without the quotation marks)
Notes: There is a space character between Outlook and the forward slash (/).
3. Click OK.
Step 3: Create a new profile
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If this issue persists, I suggest that we create a new Outlook profile. A new profile is a new environment for us to use Outlook. To create a new profile is only for a test to see if the problem is related to the corrupt profile of Outlook. Creating a new profile will not do any damage to the old profile. Please refer to the following article to create a new profile in Outlook.
829918 How to create a new e-mail profile in Outlook 2007 and in Outlook 2003
http://support.microsoft.com/default.aspx?scid=kb;EN-US;829918
287072 How to create a new e-mail profile for Outlook 2002
http://support.microsoft.com/?id=287072
195718 OL2000: (CW) How to Create a New E-mail Profile for Outlook
http://support.microsoft.com/?id=195718
Please try the above steps in your earliest convinience. If there's anything unclear, please feel free to post back.
Best Regards,
JohnJr
MCSE 2003