What 2 windows? You either have to import it or enter it manually.
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. How to import your 1099
https://ttlc.intuit.com/community/entering-importing/help/how-do-i-import-my-1099/00/26254
Or 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
