I tried again over the weekend and still the cost basis isn't updated automatically. I tried uninstalling TurboTax and reinstalling it from scratch, and starting an entirely new tax file as well, so it was all fresh - same thing. Then, I went ahead and copied down the cost basis Turbo Tax calculated, and entered it manually (with the purchase date and short/long). I kept a close eye on the amount of tax owed, and it matched up with the amount I estimated that it should be, so I am pretty confident it should be correct (I am not familiar with the form, but if the end result is the right amount of tax paid, should be good). The disqualifying distributions that my company listed on my W2 matched the amount calculated by TurboTax, not to the cents, but to the whole dollar. That's better than its been in previous years when its within a few dollars. I feel pretty good that its accurate now. I haven't actually pulled the trigger and filed yet, but I'm a little afraid that the next update could mess it up, so I am writing down the amount owed/refunded, just in case it changes with an update. Best of luck to everyone with this issue.
