Have you set your browser to clear your cookies when you close the browser? If you do that then you'll always have to login, either manually by typing it or automatically by using your browser's "remember this password" feature (or a 3rd party add-on like LastPass).
I don't normally clear cookies (it was an attempt to resolve the issue).
I think I've figure it out:
I have my personal JIRA dashboard as a pinned tab. That never auto-logs-in when I restart my browser (though clicking "Log in" doesn't require re-auth).
Whenever I open any JIRA ticket, that does in fact auto-log in, and then refreshing the dashboard shows it is logged in as well.
So apparently you have a bug that JIRA ticket pages log in automatically but dashboards don't.
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