HubSpot's KB: the desktop add-in inserts templates, snippets, documents and meeting links while composing. HubSpot lists it as in maintenance mode; the Office 365 add-in has its own guide.
1. In HubSpot
The relevant screen in my demo portal.
Attachment logging (1) and the extension default (2).
2. Worth knowing
New rollouts may be better on the Office 365 add-in.