Hello Alastair,
I would start searching for a pattern regarding the problem occurrence. Trying to answer some questions like:
- What the users with problem have in common? (same browsers, permissions, same project used, same issue types)
- When this problem started? Is there any recent change in the system that could be related to this? (add-on installation, upgrade, workflow configuration)
Then try to cross the possible information from the problem with the information you can get from the system:
- Logs (Try to gather some information from the logs <JIRA_INSTALL_FOLDER>/logs)
- Validators and postfunctions used in the workflow Create transition
- Browser development tools
- ...
In case you cannot find a solution, please open a ticket at support.atlassian.com
I hope it helps.
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