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Maybe you are in the wrong kind of 1099.
Enter a SSA-1099, SSA-1099-SM or RRB-1099 under
Federal Taxes on the left side or top
Wages and Income
Then scroll down to Retirement Plans and Social Security
Then the second line - Social Security (SSA-1099. RRB-1099) - click the Start or Revisit button
There should be a screen with a column of boxes. 2 columns if you are married.
I couldn't post a screenshot right now. Do you get a screen similar to this one?
See my screenshot at the end of this thread
https://ttlc.intuit.com/community/retirement/discussion/social-security-tax-withheld/00/156685
You should be able to post a SSA-1099 to both Online and Desktop.
Log into TurboTax.
The input screen is as described above and does have Box 5 as the first entry.
Also, be sure you have a SSA-1099 Social Security Form.
Please contact us again and provide some additional details.
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