We had often the problem, that HubSpot was not activated in Gmail. Is there an option to automatically log in to HubSpot / activate the Gmail extension as soon as Gmail opens?
Another option is to use a third party app to log your emails in HubSpot as this will automatically log all your emails without having to install the plug in or remember to activate the extension.
In most cases, the extension will keep you logged in and start automatically as long as you don't log out or clear cache/cookies. I typically only have to log in once every couple of weeks, if that.
Are you frequently clearing cache? Did you check the box to have HubSpot remember you on that device?
Josh
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Josh Curcio HubSpot support and inbound marketing for OEMs, contract manufacturers, and industrial suppliers. HubSpot Platinum Partner & HubSpot Certified Trainer