Stripe Billing isn't handling our edge cases well

Got it — Stripe Billing is great for the common cases, but edge cases can get painful fast.

If you want, I can help you think through the exact failure mode and design a workaround or replacement. To make this useful, send me any of:

1. What’s not working

   • proration issues
   • mid-cycle plan changes
   • multiple subscriptions per customer
   • usage-based billing
   • trials / coupons / credits
   • dunning / failed payments
   • taxes / invoices / revenue recognition
   • seat-based billing changes
   • grandfathered pricing
   • cancellations / pauses / refunds

2. Your current setup

   • Stripe Billing products/prices/subscriptions?
   • Checkout, Billing Portal, or custom flows?
   • one-time + recurring combined?
   • any metered usage or credits?

3. The edge case behavior you want

   • “If X happens, charge Y now, next invoice should Z”
   • “Don’t prorate when…”
   • “Allow overages but cap at…”
   • “Switch plans but preserve discount until…”

4. What Stripe is doing instead

   • wrong invoice amount
   • duplicate charges
   • subscription item mismatch
   • tax unexpected
   • invoice timing off
   • webhook/state race conditions

If helpful, I can also do one of these:

• debug your Stripe flow
• suggest a simpler architecture
• design a custom billing layer on top of Stripe
• compare Stripe Billing vs alternatives
• help write webhook/state-machine logic

If you paste the specific edge case, I’ll help you reason it out.