If you are fighting with App for Outlook and custom security roles you aren't alone. Turns out OOB security roles are special as they don't require create currently the "App" entity. However, if you even copy an OOB role like Salesperson to let's say "Saleperson Dave" App for Outlook will stop running unless you change that role to have Read,Write and Create on the entity "App". Normally the OOB roles just have Read on the App entity. This is a known issue that Microsoft is investigating - you can read more about the work around here