Ribbon behavior using Outlook 2013 vs IE

We are running CRM 2011 on-premise and using the 2011 CRM for Outlook client RU 18.
Most users are still running Office 2007 and the issue below does not occur as far as I know.  However some users are now running office 365 and issue below occurs. It does not occur when using IE (users are on IE 11)
Issue : When attempting to create a new record on a custom entity using outlook client via outlook 2013 an error occurs.
The error received is from a web-api call that is custom built.  These web-api calls get fired when opening an existing record to determine user roles etc.  The buttons that fire these rules are not displayed unless the formstate = existing (among
other rules). We did not have a similar rule on the ribbon button enable rule to check of formstate= existing.
In IE this works fine. However using the new button in OUtlook it appears the enable rule still fires. In some cases these custom web-api calls are supposed to pass an entity guid, which in this case there is none yet. 
We have modified the enable rules on several buttons to specifically account for the formstate rule and this seems to help.
Has anyone heard of anything similar. Again as far as I know this started to happen when Office 365 /outlook 2013 was installed.
Robert

Hello IMPACTMatt,
I'd say a cookie is suggesting the username. She has inherited a computer from someone else, right?
Regardless of that, can she log in?
Best regards George

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