Yes you have to report all your sales. Doesn’t matter what you did with the proceeds. You can deduct a net loss on your tax return, up to 3,000. The rest you carry over to next year.
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
You need to use the Online Premium version to enter a 1099B for sales. Or any of the Desktop programs. All the Desktop programs have the same forms. You just get more help and guidance in the higher versions.
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.
