User can not see Started Workflow in Outbox.

[Rick Sample]

I have an issue that is causing me concern.
 
I have a user that execute a WF and can not see it in his outbox.
I thought it may have been just date filtering setting but I do not 
see it in his outbox via SWI5 either.
 
I look in the inbox of the user it was supposed to go to and it is 
where it is supposed to be with the initiators name that executed it. 
Why?
 
Any help would be appreciated. 
Thanks!