.doc files not going to new workflows

We have a category called Support Documents that include files with .doc, .docx, .xls, and .xlsx. and a single workflow for files in this category.

We now need to make different workflows for different types of .doc files.  I've tried to assign the file to a particular workflow based on words in the Title property, but it keeps getting assigned to the default workflow.

I'm at a bit of a loss here - what should I do?

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