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?
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