I've seen this as well, though I don't get the error. Instead, the
Outlook COM Addin that runs in Outlook doesn't execute during the
ItemSend event. If Outlook is already open, events fire as expected.
Frustrating.
I'm wondering if this isn't another of the Outlook 2003 security
"features."
Best,
-Tony
It sounds more like an addin is causing the problem because it doesn't load
when outlook is loaded in a hidden state and that may keep outlook from
loading enough to use send to. Disable all addins and test it to identify
the problem addin.

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Diane Poremsky [MVP - Outlook]
Author, Teach Yourself Outlook 2003 in 24 Hours
Coauthor, OneNote 2003 for Windows (Visual QuickStart Guide)
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> I've seen this as well, though I don't get the error. Instead, the
> Outlook COM Addin that runs in Outlook doesn't execute during the
[quoted text clipped - 6 lines]
> Best,
> -Tony