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My Stripe Tax Story

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Re: My Stripe Tax Story

#2
He wasn't collecting address information for US customers, so the invoices hung in a pending state. He didn't check to make sure the integration was working correctly until a customer emailed him to ask why they hadn't been billed three months later, so there were a lot of invoices to clean up, which he apparently found to be very annoying.

Re: My Stripe Tax Story

#3
(I work at Stripe.) This was a painful read. I'm sorry. We could have done a lot better. We're working on remediations now, and we're sending another, corrected email tonight with the updated CSV file of failed invoices as of March 1st.

Re: My Stripe Tax Story

#4

He wasn't collecting address information for US customers, so the invoices hung in a pending state. He didn't check to make sure the integration was working correctly until a customer emailed him to ask why they hadn't been billed three months later, so there were a lot of invoices to clean up, which he apparently found to be very annoying.

> He didn't check to make sure the integration was working correctly

But what is your definition of "check to make sure the integration was working correctly"? Once you know what was going wrong, it's easy but unhelpful to say "you should have checked to see if that thing was going wrong".

He had dashboards indicating "situation normal", and there was no specific advice that he check that an avalanche of draft invoices was silently piling up.

Given that Stripe advertises itself as making payments easy, it seems like it should take responsibility for making them easy, instead of having hidden pitfalls that silently tank your revenue.

Re: My Stripe Tax Story

#5

He wasn't collecting address information for US customers, so the invoices hung in a pending state. He didn't check to make sure the integration was working correctly until a customer emailed him to ask why they hadn't been billed three months later, so there were a lot of invoices to clean up, which he apparently found to be very annoying.

> He didn't check to make sure the integration was working correctly But what is your definition of "check to make sure the integration was working correctly"? Once you know what was going wrong, it's easy but unhelpful to say "you should have checked to see if that thing was going wrong". He had dashboards indicating "situation normal", and there was no specific advice that he check that an avalanche of draft invoic…

In the post he says:

>I had noticed that my cashflow for the previous 2-3 months seemed to be tanking a bit

A bit? Revenue from all US customers went to zero for three months! That should have been a giant hole. This is like driving your car into a lake, hearing a "bang" as the engine explodes, then complaining that there's no "you have driven into a lake" warning light on the dashboard.

Re: My Stripe Tax Story

#6

Earlier quoted context omitted.

> He didn't check to make sure the integration was working correctly But what is your definition of "check to make sure the integration was working correctly"? Once you know what was going wrong, it's easy but unhelpful to say "you should have checked to see if that thing was going wrong". He had dashboards indicating "situation normal", and there was no specific advice that he check that an avalanche of draft invoic…

In the post he says: >I had noticed that my cashflow for the previous 2-3 months seemed to be tanking a bit A bit? Revenue from all US customers went to zero for three months! That should have been a giant hole. This is like driving your car into a lake, hearing a "bang" as the engine explodes, then complaining that there's no "you have driven into a lake" warning light on the dashboard.

People are always going to have this feeling of "I can't believe Y was not as conscientious as I assume I would have been in X situation". It's hard to put ourselves in other people's shoes.

I don't know what else is going on in this guy's life, except he's got kids so that's already a lot.

Re: My Stripe Tax Story

#7
Is there an extra fee for this Stripe Tax integration extra ? If not a separate fee, will they refund partially given that no alerts or alarms were raised for this behaviour ?

All I can say is they probably built this in a hurry and the workflows weren't really tested or checked by humans. I call it "But CI is green" syndrome.

Re: My Stripe Tax Story

#8

Earlier quoted context omitted.

> He didn't check to make sure the integration was working correctly But what is your definition of "check to make sure the integration was working correctly"? Once you know what was going wrong, it's easy but unhelpful to say "you should have checked to see if that thing was going wrong". He had dashboards indicating "situation normal", and there was no specific advice that he check that an avalanche of draft invoic…

In the post he says: >I had noticed that my cashflow for the previous 2-3 months seemed to be tanking a bit A bit? Revenue from all US customers went to zero for three months! That should have been a giant hole. This is like driving your car into a lake, hearing a "bang" as the engine explodes, then complaining that there's no "you have driven into a lake" warning light on the dashboard.

You are assuming that a large number of their customers are from the U.S. not knowing what business they are in, their customer pool might be 90% Canadian. The whole world doesn't necessarily target U.S. customers.

Re: My Stripe Tax Story

#9

He wasn't collecting address information for US customers, so the invoices hung in a pending state. He didn't check to make sure the integration was working correctly until a customer emailed him to ask why they hadn't been billed three months later, so there were a lot of invoices to clean up, which he apparently found to be very annoying.

You don't normally have to give Stripe location information for US customers. The problem happened when he enabled tax support for Canadians.

Enabling tax support in Canada breaks US subscriptions... who knew.

> I built out my Stripe Tax integration, made sure I had all the addresses I needed for my Canadian customers (Canada is the only jurisdiction I run my business, and therefore only need to charge tax to Canadian customers), and updated all my customer subscriptions, awaiting the glory of automatic GST, HST and PST to be charged, and Stripe Tax taking all my headaches away.

> I deployed it on November 6, 2021, the same day that Stripe stopped billing a significant number of my customers, left all their invoices in a Draft state, and didn’t tell me about it.

Re: My Stripe Tax Story

#10

Is there an extra fee for this Stripe Tax integration extra ? If not a separate fee, will they refund partially given that no alerts or alarms were raised for this behaviour ? All I can say is they probably built this in a hurry and the workflows weren't really tested or checked by humans. I call it "But CI is green" syndrome.

Yes. it's 0.5% per payment* on top of 0.4% per "invoice". Quite hefty fees considering credit card fee is 2.9%
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