My Stripe Tax Story

It's always a risk to make assumptions, but I don't think this specific assumption was unreasonable.

Anything to do with money and tax internationally is complex, and it should be monitored at least until you know it works, e.g. put dates in your diary to check your first international customers paid the right tax?

I must say, the Stripe chat session support people are heroes when you consider the breadth of the topic area they are covering, and some of the random chat abuse they must get from confused end user customers, and I don't think they deserved the fake-swear or some of that tone.

Especially when the writer concedes he could have been productive in the meantime. Some of this stuff just goes with the territory, and they are a business, not magicians.

There's also a sandbox -- is the writer saying there was no way to find this out through testing in the sandbox?

I have had one experience like this where I got a result I did not expect on live compared with the sandbox, which came down to quirks of my sandbox testing.

Specifically to do with trying to speed up testing [0]. I was getting payment collection tested within the day, but that meant a setting that affected something that happened at the end of the billing day never showed an impact in testing; on live it always would. That outcome, I think, could have been covered in a footnote like the one that was added after the writer's experience.

The reality is that Stripe's documentation is heroically excellent (a counterpoint to the Hugo story yesterday) but their system is vast and has all sorts of complex real-world interactions. They have shown they are responsive by correcting the documentation going forward.

[0] About the only thing I wish you could do that you cannot, is accelerate time in the sandbox, to make stuff like this easier to test. I understand why you can't but this is my fantasy. A stateful Stripe Connect mock would be useful though; I had to add one to my app.

I am a highly anxious person, and it can be debilitating.

But when you're talking about taking payments and arranging the collection of tax, I reckon it's wise to treat your anxiety like a colleague. Give it the best chair; make sure it has lunch, and not too much coffee. And listen.

It's your responsibility but only over a threshold (and the rules / amount are different in every US state)

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.