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> The only reason for software to be existing is to NOT mandate users to check stuff manually.

Software exists so users don't have to do stuff manually. But people should absolutely check on things periodically. That doesn't mean it's always necessary to check every single transaction, but spot and sanity checking is mandatory diligence, IMO. I pay my CPA to do my taxes so I don't have to do them myself, but of course I sanity-check the end result before signing off on it.

And OP made a huge change to how he was invoicing/taxing his customers, and then didn't verify that things were working properly after making the change? That's just irresponsible.

Stripe's documentation and API could probably stand to improve here, but that's the nature of products and API UX: never perfect. I do think it's pretty lame that Stripe's support and product people were evasive and did a bad job of admitting that the product had some rough edges that need to be improved.

But... c'mon. Not checking something as basic as "are my customer's payments being processed properly" after making a large change to the payment processing pipeline, and only finding out something was wrong, three months later, after an honest customer asked why they weren't being billed? That's pretty bad.



At EOD how many invoices are in draft status?

Is it more than 0?

Is it more than yesterday?

Seems like 2 or 3 dead simple controls on his part could have avoided this.




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