File Upload Not Showing on Form Through Automation

I was able to create a form and add the file upload option. This is a form that needs to be filled out by over 70 different vendors and I am using automations to send out on a 6 week cadence. When I check the form via Open Form on Smartsheet, the file upload section is showing just fine. However, when the form is sent out via the automation, the file upload section is no where to be found.
Answers
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When you send out the reminder every 6 weeks, are you sending it as an update request? (That's what your second screenshot looks like.)
If that's correct, just make sure you're including the "An Attachment" in the fields you're sending. Just keep in mind that they will be able to view any current attachments on the row, as well as add new ones.
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