Like many FAANG employees, the IRS calculates my withholding incorrectly. I got a letter in January announcing that I didn't withhold enough and applying a penalty.<p>I spent two hours on the phone on a Friday being bounced around the IRS. Talked to plenty of people, but each one thought I was someone else's problem. I tried again on that Monday: waited on the phone for two full hours before being unceremoniously hung up on by their automated system.<p>FWIW, it seems there's the luck of the draw on three distinct systems (robot + touch dial menu + human operator, robot + voice menu + human operator, or just robot + voice menu). They're incompatibly dysfunctional. The first one is when I got bounced around. The second one, the operator hung up on me because she couldn't hear callers routed through that system. The last one was where I spent 2 hours without a human before being dropped.<p>Calling the IRS was even more of a pain in the ass than I anticipated. I gave up and paid the penalty. (And that was in January!)