Welcome to community! Can you elaborate more on your question on what you mean by make one of the statuses required when field is marked "yes"? Is statuses a field as well or you're referring to the workflow status the user will be transitioning to?
Please can you also explain your use case here? What purpose does it serve to a user using it? A Status in itself basically just display the progress of the issue or ticket. I don't particular see a need why it should be required. Most users would rather hide the status but making it required serves no purpose in a workflow design. By default the status being a system field can't be configured to be required. Probably expanding on your use case we can better explain what else you could try.
Thank you, some of our tickets must to go via security review before completing the task, some of them don't. I want the ability to mark a field named "Requires a security review" if this field marked as yes, I want to obligate the transition via the workflow status "Security review"
I remember a similar requirement which I found here. The summary was that you cannot skip workflow steps but based on a field you could decide if an user has to take one or a different transition.
Using conditions within workflow you can make sure the right transition is offered.
Let us know if the suggestion works for you also.
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