Yes it was the macro security. This is one of the first things I
checked but I ruled it out quickly as I would set it to high, and it
would still work. What wasn't clear was that Outlook actually requires
a restart for that change to take effect. I tried again on mine,
setting it to high macro security, restarting Outlook and sure enough
my code wouldn't run.

Would have been nice if changing that setting gave an indication that I
need to restart Outlook for the setting to take effect, or at the very
least an error in Outlook similar to Excel when your macro secuirty is
too high for your scripts.

Thanks.