You can't enter stock sales in TurboTax Free Edition. You will have to upgrade to Premier, or use any edition of the CD or download TurboTax software.
In TurboTax Premier, after you enter the name of the brokerage, you will get a screen with two choices: "I'll enter one sale at a time" or "I'll enter a summary for each sales category." Select the second option, and it will then give you boxes to enter the total proceeds and total cost, and select the sale category (short-term or long-term, covered or noncovered). After that screen, you will get a screen that asks if you need to enter another sale, meaning totals for another category. You have to enter separate totals for each category.
You cannot make entries directly on Schedule D. In TurboTax Online you cannot make entries directly on the forms at all. Everything has to be entered through the question-and-answer interview. Even in the CD or download TurboTax software, you do not make any entries on Schedule D. If you don't want to use the interview, you enter all the information on either the Form 1099-B Worksheet or the Capital Gain (Loss) Transaction Worksheet. It flows from the worksheets to Schedule D.
Entering investment sales in forms mode in the CD/Download TurboTax software is very complicated and error-prone. I strongly recommend using the Step-by-Step interview.
More likely he has a large number of transactions and doesn't want to enter them all individually.
You can't enter stock sales in TurboTax Free Edition. You will have to upgrade to Premier, or use any edition of the CD or download TurboTax software.
In TurboTax Premier, after you enter the name of the brokerage, you will get a screen with two choices: "I'll enter one sale at a time" or "I'll enter a summary for each sales category." Select the second option, and it will then give you boxes to enter the total proceeds and total cost, and select the sale category (short-term or long-term, covered or noncovered). After that screen, you will get a screen that asks if you need to enter another sale, meaning totals for another category. You have to enter separate totals for each category.