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Have you tried doing this in the transition's post function?
Here is an aswer that resolved the same question of another community member: https://community.atlassian.com/t5/Jira-Software-questions/make-log-work-mandatory/qaq-p/1580841#M116764
Are you in a teams managed project? The config I am referring to is only available for company managed projects.
In order to manage the workflow of a Company Managed Project you need to be a Jira administrator. The workflows are under settings -> issues -> workflows.
Some documentation on https://support.atlassian.com/jira-cloud-administration/docs/work-with-issue-workflows/