It is not possible to "upload" or import a SSA1099. You just have to key it in by hand.
As for your 1099R, you might be able to import it if the financial institution that issued it is partnered with TurboTax to allow it or you might have to choose "I'll type it in myself."
Go to Federal> Wages & Income>>Retirement Plans and Social Security (SSA1099 and 1099RRB) to enter your SSA1099.
To enter your retirement income, Go to Federal> Wages and Income>Retirement Plans and Social Security>IRA 401 k) Pension Plan Withdrawals to enter your 1099R.
**Disclaimer: Every effort has been made to offer the most correct information possible. The poster disclaims any legal responsibility for the accuracy of the information that is contained in this post.**
