Workflow Not Tiggering

I have workflow with a custom function that at the end updates a status field in our cases module. There is then a workflow setup that is supposed to trigger when the status field is updated. When I test the code from "save and execute script", it works perfectly the update triggers the workflow and there are no issues. However, when a new case is opened via the webform the custom function executes like it is supposed to and updates the status but the workflow that is supposed to be triggered by that update doesn't work