Go to Income/Investment Income and click the Update button for "Stocks, Mutual Funds, Bonds, Other". Then click "Yes" that you sold investments. Then click "Yes" that you have a 1099B. I'm assuming that you will type entry yourself, so click "I'll type it myself" and "Continue". Enter brokerage name and "Continue". You can enter each sale one at a time or enter a summary for each category. I'll assume that you will use the summary for each category listed on your 1099-B. For each category (short covered; short uncovered; long covered and long uncovered): enter the proceeds and your cost basis and select the sale category for your 1099-B holdings for each category, Your short-term sales will get category A or B depending on whether your brokerage reported the basis (covered) or did not report the basis (non-covered). Click "Done" when the first entry is complete and follow the prompts to click "Yes" to add another sale category and repeat the process. Your long-term holdings will get category D or E depending on whether your brokerage reported the basis (covered) or did not report the basis (non-covered). Be careful to match the 1099-B data for each of the possible categories.
