Hello,
I have a similar issue to here: https://community.atlassian.com/t5/Jira-questions/Simple-Automation-Rule-Not-Working/qaq-p/1610214
The user's problem was solved in this case by Atlassian telling him that next-gen projects handle request types differently, but I am running a company-managed project and their solution does not make sense to me.
I have an automation that creates subtasks for a particular request type when it transitions through a workflow phase.

This condition fails roughly half the time the automation runs, even when the request type is the correct request type. Recently, it worked for one agent and then did not work for another agent on the same day, even though both are in the same groups and have the same roles. The actor is Automation for Jira. I have not been able to make it fail for myself.

Does anyone have any suggestions?