I use the Hubspot sales add-in and there are a number of issues with it. First, even though I always specify 'remember me', the password always has to be re-entered.
Also, within the last few days it keeps logging out of hubspot so that for every email I send, I have to log back in to get it to save. Super annoying!
Lastly, the add-in used to have an option to specify email addresses that you don't want to save to HS. That option has now disappeared.
I feel your frustration. It happens to me often that even though I ask it to remember me, it keeps logging me out. I know for myself though that being in an agency, I have access to different portals, sometimes with different email addresses. I guess that's the reason for it to log me out on a regular basis. Do you have access to multiple portals?
As to the option to not log specific emails, that's still available within the Hubspot portal. Here's the Knowledge Base article explaining how to do it.