Workflow not triggering even on correct start condition

Hello,
I'm working on a flow currently where it is not being triggered even though the condition I defined in the Start trigger is met in the document's index fields. Ideally, the workflow should start when the "Status" field changes from NEW to WORKFLOW.

When I import a document it starts off with its "Status" field set to NEW
I have an autoindex job that checks/retrieves some data from another file cabinet, then makes that change in the document's "Status" field. If I check the document's history, it clearly says that the field was changed from NEW to WORKFLOW. Yet for some reason, the workflow is not triggered when the field is changed. Has anyone run into a similar issue before?

Thanks.

Dear Luis Flores! It looks like the Community cannot answer your question. That's why we have opened a Support Request with the Number SR-148123-B6M4T for you. A Software Support Specialist will contact you directly to follow up. We will update this thread with the solution as soon as we have resolved the Support Request. With best regards, DocuWare Support Team

When this happens I typically check to ensure the workflow has been published (I've missed that step before) and then I check to ensure that the Background Process Service is running (sometimes this will fail to start in a VM for some reason).  What version of DW is this?