Same issue. We just switched to Office 365 after being told the functionality of the plugins operated the exact same as Gmail. It is far from it. The fact that our reps have to click a button for every email to auto-track it seems a very unnecessary task and waste of time. If a team of 10, send 100 emails a day each, and it takes 2 seconds to click and load the side-bar, that’s 38 hours of wasted productivity every year.
Please can we get a fix on this ASAP. I spoke with Office 365 and they said the quickest way to solve this is for Hubspot Dev team to raise a ticket with their Dev team and go from there.