Outlook client only rule will not work on some computers

I have a user who created a client rule, in Outlook 2010 64bit on a  windows 7 64bit machine.  Where on a hosted Exchange 2010.

Apply this rule after I send the message

sent to Jane Doe

and using the meeting request form

assing to the Jane Do category

However the meeting will not show up on the calendar with the assigned category color. 

I've tested this on 5 different PCs with the same configuration. Three do not work, two do.

Any ideas as to why or how to get this to work?  It seems a simply enough rule.