No other user reports this issue occurring, then again very few users use the encryption tool with regularity. No matter what, however, the add-ins go back into inactive status as soon as the app is closed and re-opened. In fact, the one add-in that is the most critical (the encryption add-in) is listed as causing Outlook to open slowly, but it is marked as 'always enable this add-in'. Using some good ol' Google-fu, I find several dozen sites pointing towards a 'feature' that was added into Outlook 2013 that disables add-ins that cause Outlook to open slowly and the way to ensure an add-in always loads is to use the application's 'slow and disabled COM Add-ins' and/or regedit to add/tweak a few keys. Close and reload, all the same add-ins are inactivated or disabled. Re-enabling/activating them works, but only for a single instance of the application. The investigation: Nearly all of the user's Outlook add-ins are disabled or marked inactive in the Outlook options. If the add-in is included on the list, select it and click Enable. From the Manage drop-down menu, choose Disabled Items and click Go. But when I debug the project from VS 2012, it opens up Outlook 2013 but I dont see 'Add-Ins' tab next to 'View' or 'Developer' tab.

Those two buttons will show up two forms respectively. Microsoft Outlook 2010, 2013, 2016 users: Choose File, Options from the top menu and go to the Add-Ins tab. I built a simple outlook addin from VS 2012, in which I have two buttons in ribbon (Designer). The problem: A user reported that our encryption add-in for Outlook is missing from her toolbar. If the add-in is included on the list, select it and click Enable. No matter what I seem to do, Outlook keeps having a mind of its own.

I've been banging my head against the wall on this one.

Add ins outlook 2013 tolbar