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There are more than a dozen kinds of 1099's. What kind of 1099 do you have?
1099-NEC
A 1099NEC is for self employment income. You can't upload that. You have to type it in manually.
You can't enter a 1099NEC on the Free Edition. You can enter Self Employment Income into Online Deluxe but if you have any expenses you will have to upgrade to Premium version. Or use any of the Desktop CD/Download programs.
How to enter income from Self Employment
https://ttlc.intuit.com/community/self-employed/help/how-do-i-report-income-from-self-employment/00/...
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