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You may find TurboTax Live helpful, but if you are using Premier or Self-Employed, those both have phone support for stock transactions included. So, you may not need the extra expense of Live. In any case, I will leave the information below. TurboTax does an excellent job of walking you through stock transactions, especially employee stock. I suggest you first try using the software to enter your transactions. If you need help, you can ask for help here (there are lots of people in this forum that work with employee stock) or contact phone support. If after that, you are still not sure about what is reported on your tax return, then try out TurboTax Live.
What is the TurboTax phone number?
Large company or small?
Usually a large company will tell you via reports how much stock you bought and what you paid for it.
Your question is unclear. Is this a problem in that that you don't know the basis for the stocks sold, or you do have this information but don't know how to enter the information about your purchases "over many years?" Also, you don't state if these purchases were at "fair market value" or if you received a discount when you bought the stock. The latter situation can be a bit tricky.
Assuming for the moment that you do know the basis for all those lots, those lots were not purchased at a discount, all the purchases make the lots long term, and the basis isn't being reported to you on the 1099-B, (a lot of assumptions), then you can simply enter the total basis in the basis box and the word "various" in the date acquired field.
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