Workflow doesn't seem to want to trigger

I'm using an Autoindex to kick off a workflow, the reason is because I want the to send an email/notice when a date is within the next month but I need the system to know not to run the Workflow every time the Autoindex is run, which will be every day. The trigger conditions for the workflow are if the index entries of the document were changed and "For new documents". 

If All of the following conditions before index modification is/are fulfilled

Document Type                       Equals                      Placebo
Status                                      Does Not Equal        Expiring

If All of the following conditions after index modification is/are fulfilled
Document Type                       Equals                      Placebo
Status                                      Equals                      Expiring

The Autoindex appears to be working, because I leave the Status field blank when storing the document, and when I run the Autoindex, the Status field says "Expiring", which is what I've set the Autoindex to do when a date field is within the next month, but the document has no workflow history.

Any ideas as to why this workflow isn't triggering?

Dear Rhys Woolley! It looks like the Community cannot answer your question. That's why we have opened a Support Request with the Number SR-179755-P9Y3Q 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