Hi @Jesse Eversole,
This is true. I had taken advantage of this on Jira Server before we migrated to Cloud and that functionality no longer worked upon migrating to the Cloud platform.
If possible, I'd recommend getting/generating a test server license and spinning up a test Jira Server you can use for these types of experiments.
I hope that helps!
"The end goal is to call an external server that updates the issue with any changed status of the issue"
is something you should be doing with webhooks or post-functions if you mean Jira needs to tell another server something, or the REST API if it's the other system wanting to update Jira.
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