You want your workflow to fire once more after a field value is updated via workflows. However, for some reason, the workflow is not triggering.
Remember that workflows don't have any order of execution. One can't ensure that they follow a specific order. Salesforce provides a checkbox for the field updates to re-evaluate the workflows after the fields are updated.
The following screenshot shows the settings on the field updates that, as an administrator, one needs to apply to ensure that workflow rules are triggered again:
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