I asked ChatGPT for tax help—experts say I fell into a classic trap

Skip Navigation Related Stories Work This 3-step technique helps you get the   most out of AI tools, experts say Land the Job Cold applying is still the No. 1 way to get a   new job—but this method is growing Raising Successful Kids How to use AI for parenting advice: It can   be 'quite scary,' says researcher Leadership Zillow CEO: Even senior-level job   candidates make this interview mistake Land the Job This online red flag could cost you a   job, say staffing agency founders For most of my adult life, I've enjoyed a relatively straightforward tax situation . In most years, I merely made sure the income from my W-2 was correct and clicked through my preferred tax software's questions to the end. No dependents, no side hustle income , no property in my name. This past year was a little different. After years of buying stock through my company's employee stock purchase plan, I sold the majority of my shares to begin raising funds for my upcoming wedding. There are some relatively tricky rules around selling these shares, but the gist is, these plans allow employees to buy stock at a discount to the actual share price. So determining how much money you made (in which case you owe capital gains tax ) or lost on the sale of your shares requires some calculations. So I did what about 1 in 5 taxpayers are doing these days, per a recent survey from IPX 1031 : I asked AI for help. I did so skeptically. …