Maybe the plugin cache is corrupted. First try uninstall/reinstall (you don't lose data). If that doesn't help, try clearing the plugin cache.
I do not see any errors in the logs .
This is an example of an older task with a Draw.io attachment that works, can edit .
But the add is missing form the menu.
draw example.png
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Is there anything in the JIRA logs about draw.io failing to startup? Could I get a screenshot of the menu in question please?
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What version of draw.io do you have? What versions of JIRA did you upgrade from/to?
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