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In a nutshell:

Yes, you will pay Social Security taxes on your earned income. In addition, if your total income is high enough, up to 85% of your Social Security benefits will also be considered taxable income.

Yes, TurboTax should be able to do the math for you.

Do note that your employer’s default tax withholding will be based on your salary at that employer only. You may want to adjust that withholding to reflect the fact that you have other sources of potentially taxable income that will be considered in your total tax picture.

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