The issue I'm having is that licenses aren't being renewed correctly. Licenses are expiring before the new billing cycle can be created. This results in the customer being billed for the second month, but not having an active license to go along with it. Looking at the commerce_license table, I'm seeing that licenses for recurring orders are being created with expires_automatically set to TRUE, not FALSE like commerce_license_billing indicates. I'm currently running tests to see if this is the root cause.
The issue of users being billed for an order with no active licenses also seems like it ought to be looked into.
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