In fulfill#ProductSubscriptionResource, there is a comment determine fromDate (either last Subscription.thruDate if in future, or nowTimestamp; however, that 'if in future' bit is never actually tested for in the following logic.
What has occurred, is that my account in our system had an activate subscription that ran up to August 1st. But then, we implemented a change to our database process, and now local development systems no longer have correct production credit card processor settings. So, the nightly process that renews the monthly subscription failed(this is actually fine), so as of right now(August 18th), I do not have an active subscription.
I then attempted to create a new subscription(using prorated days, 14, to round out to the end of the month). The linked service above then attempted to extend the subscription from August 1, through August 15th, instead of $now to August 31.