Every software company you look at will proudly tell you it integrates with the big vendors in its space. Sounds like a feature. Sounds finished. I built a platform that lived or died on those integrations, eleven of them, and I’m here to tell you every single one is a living thing that breaks when the vendor changes anything. “We integrate with them” is not a feature you bought once. It’s a maintenance bill that shows up forever. Here’s what that actually looked like. One vendor’s numbers were inflated fifteen times, and they looked completely normal. A data feed I was pulling from sent running totals, and the code was reading them as if each one was a fresh separate number, so it stacked them on top of each other. A customer’s production got inflated by roughly fifteen times. The thing that makes this scary is the numbers weren’t obviously crazy. They were just wrong enough to be believable, so they flowed straight into invoices and into regulatory filings before anyone caught it. Wrong but plausible is the worst kind of wrong, because nothing alarms. It just quietly poisons everything downstream. Every connector broke in its own special way. Four different vendor integrations, four completely different headaches. One double-counted whenever the data windows overlapped. One quietly skipped the most recent full month of data. One used a login that expired every fifteen minutes and had to be constantly refreshed or everything stopped. One had no real security at all and a hard limit on how often you could even ask it for data. There is no “we integrate with vendors” as a single solved thing. Each one is its own separate ongoing liability. There was a second, invisible channel doing the real work by hand. Some of the regulatory filings that were supposedly handled by the platform were also being done manually, outside the system, by a person. Which means the software’s records and the official records could quietly disagree. “The platform shows it was filed” was not the whole story, because a human was also in the loop and nobody had written that down. Here’s what I want a buyer to take from this. When a company says “we integrate with X, Y, and Z,” that’s not three features. That’s three living dependencies, each one of which breaks when the vendor on the other end changes something, and each one needs a human who understands it. Count integrations as ongoing cost, not one-time wins. And ask the uncomfortable question: is this software actually the only system doing the job, or is someone also doing it by hand where you can’t see? If you’re looking at an integration-heavy business and want someone who’s maintained a pile of these to tell you where they’ll actually break, reach out. First look’s free. It’s the work I do now. For the people who’ve bought integration-heavy companies: what broke first after you closed? I’ve got theories.