1) Is the box “Created invoices even if amount is $0” checked? If not, then the invoices were not created if the amount due was $0.

The amount due could have been $0 if they checked “Show un-invoiced” transactions and “show payments”, because the previous month’s charges have already been invoiced and will not appear on the invoice. The payment is then being credited for the upcoming month’s charges.
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2) Check to see if the “Yes” box is checked at the bottom of the form
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3) Make sure the transactions required to be on the invoice are within the date range that the schedule is to run. If they start the invoice schedule on Oct 1st, but require transactions 30 days before Oct 1st, the invoice schedule will not run.
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4) Many teachers run into the “New Billing Cycle” errors when they first set up their automatic schedule.

It’s better to invoice the first month manually and then add the new students to the schedule their 2nd month.