Start with a look at the application log file. You should find it in the JIRA home directory under /logs, probably called atlassian-jira.log
The part you are interested in is the point at which you click "enable" - that should dump lots of information (including "I can't start this plugin because...." info) into that log.
Hey Atlassian community, I help lead engineering at Sentry, an open-source error-tracking and monitoring tool that integrates with Jira. We started using Jira Software Cloud internally last year, a...
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