If I manually terminate webroot and restart outlook it works fine again.
It must be protecting the Temporary Internet Files folder in INetCache as this is where the Outlook images are stored.
Can someone confirm and if there is any temporary fix that would also be nice.
Best answer by RetiredTripleHelix
It looks like some are having issues with Outlook 2016 after some recent October Updates: https://support.office.com/en-us/article/Fixes-or-workarounds-for-recent-issues-in-Outlook-for-Windows-ecf61305-f84f-4e13-bb73-95a214ac1230?ui=en-US&rs=en-US&ad=US so to me it's nothing to do with Webroot so it might be best to post at the Microsoft Community to find answers: https://answers.microsoft.com/en-us/msoffice/forum/msoffice_outlook