I've got an issue which I was trying to check in the forum but haven't found. Everytime I open Outlook desktop a logging prompt pops up and requires logging in even if I check a box to remember me. Let me know if there's a way out or I will have to delete the extension from Outlook.
I have had the same problem as you for a year, and nothing has ever fixed it.
I just google searched again today, and came across the above as a possible solution - but my HubSpot doesn't have a setting anywhere to "customise inactive session timeout", IE my HubSpot doesn't look the same as the instructions on this link.
Can you have a try, and see if this works for you?