You need to upgrade to the Premier version to enter investments. You have a consolidated statement. That will have sections for 1099-Int and 1099-Div and 1099B. You need to enter each section in the right place. So read it carefully and look for headings.... 1099-INT for interest or 1099-DIV for Dividends or 1099B for sales.
You can enter a 1099B manually or try to import it. If you import it be sure to check it over close and make sure the cost basis got imported and is right. I import my friends accounts from Wells Fargo. It works good.
How to import your 1099
https://ttlc.intuit.com/community/entering-importing/help/how-do-i-import-my-1099/00/26254
Enter a 1099B under
Federal Taxes Tab or Personal (Home & Business)
Wages & Income
Then scroll down to Investment Income,
Then Stocks, Mutual Funds, Bonds, Other - click Start or Update
If you have a sale for shares that you bought at different times you can put various for the date purchased. But you should split the sale into 2 sales for short term and long term lots. So if you bought any shares or reinvested dividends within a year of the sale they would be short term.
