seems you mentioned JIRA prompt for admin password after 5 - 10 minutes, you may want to increase the timeout of websudo(the prompt message) as according to this documentation section.
If you're using JIRa 4.4 or above, kindly input the following code in the jira-config.properties(generate if not exist in the root of home directory) and restart after that:
jira.websudo.timeout = 10
If you're using JIRA prior to 4.4, you can edit the jira-application.properties at $jira-install/atlassian-jira/WEB-INF/classes and restart after that.
Yes, that was it. Before I knew you answered this, I found this solution via googling the error message "Administrative Retry". I created jira-config.properties with this property with timeout set to 30 minutes, and viola the problem gone.
You have confirmed what I found.
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