This is an old question, but since I had a similar issue and could not find a detailed answer to the question, I will tell you what I did for my situation. I had been using the online version but read comments that it's lacking for these types of transactions, so I bought the CD. In 2021, I sold 85 shares of stock I acquired while working for a prior company that consisted of ESPP stock (shares purchased at a 15% discount) as well as shares that were the result of dividend reinvestments. Since it was from so long ago, my 1099B had 2 lines; one line with 14 shares of covered long-term common stock that were purely dividend reinvestments from 2010 forward (I have supplemental information for this, which is how I know) and one line with 71 shares of uncovered long-term stock that consisted of 64 shares of ESPP and 7 shares of common stock that were a result of dividend reinvestments (I also had this information along with the cost basis and such because I requested it from the servicer after I sold it) . The first sale of 14 shares I reported with no problem as it was all stock from reinvested dividends. However, for the second sale of 71 shares, there was no way to break down the sale into more than one category of stock. I had to enter 2 separate sales, one for 64 shares of ESPP, and then another sale for 7 shares of regular stock (for both of these sales I kept the description of "71 of 85 shares sold" to indicate they were both related to the same line in the 1099B). I could not find any other way to do it. It will not match your 1099B in terms of the number of lines, but the total will match. I then went to the 8949 forms (you have no option to see the forms with the online version) to check the calculation of the cost basis and gain (I manually calculated this as a check to make sure that I had entered the information correctly). Note* don't forget that the discount on ESPP stock is treated as ordinary income and will be taxed at your regular tax rate based on your adjusted gross income and not the capital gains rate, so your cost basis of the ESPP stock is bumped up by that amount (since you are already paying tax on it) . It will ask you in a separate question if the amount of the discount (it will ask by the specific dollar amount) was included in your wages in your W2. However, if like me, you no longer work for the company where you bought the stock, you have no W2 from that company, so the answer is no. This is how turbotax knows to include the discount as ordinary income. Since I couldn't exactly find the answer for my specific situation, this is what I had to do to get it to work. It seems like it calculated everything correctly, so I'm guessing it's right. I hope my exceedingly long answer is helpful to someone because I was pulling my hair out trying to find a specific detailed example to point me in the right direction.
