Using the Ring/HubSpot extension for all calls using the browser, and only having the desktop program open to view the HUD. Setting the Ring/HubSpot extension for all calls to go through the RingCentral app rather than the browser resolves all of the above issues, but then he will have two apps side by side that he needs to jump between to do different functions and it introduces a couple extra button presses. The Ring/HubSpot app does not give the option for "Ask First" transfers when making calls through the app, only when making calls through the browser.