I installed the 7/5/18 update and I still am not able to save directly to Sharefile in Microsoft Office 365. It says a plug in is missing or not working. https://www.screencast.com/t/vMYoTrXPgt6 This means I have to save elsewhere then upload to the Sharefile app.
I'm on the Engineering team that works on Citrix Files for Outlook (formerly ShareFile Outlook Plug-in).
I looked at the screenshot you posted and I don't think this is related to the Outlook Plug-in, but maybe another Plug-in. The Outlook Plug-in only works within Outlook so wouldn't be visible inside Word (which is what your screenshot looks like).
Did you try the option to Repair when you received the error? Did anything come of that?
Also, in case you hadn't seen, we released Citrix Files for Outlook v6.2 yesterday and we recommend updating to the latest version.