It doesn't seem to matter if I log in and save credentials. I have to login all the time and with the cloud version of JIRA. It's just not a good use of time for a tool I use all day long.
There's something wrong in your browser settings - it's losing session info and/or cookies.
Could you try another browser (or even just incognito mode in the same one if you have that option)? Do they retain the session? What about other computers?
I agree with Nic. Just track what is happening to your cookies and you may find the source of the issue. If you don't know how to do that then please contact Atlassian Support at support.atlassian.com
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