Social Security Taxes Estimate how much of your Social Security benefit may be considered taxable. You are viewing this website at a small screen resolution which doesn't support calculators. Click here to view this calculator. Have A Question About This Topic? Name Email Address Question Thank you! Oops! Related Content Investment Challenges of the Affluent Investor Affluent investors face unique challenges when putting together an investment strategy. Make sure you keep these in mind. What's New for Social Security? There have been a number of changes to Social Security that may affect you, especially if you are nearing retirement. You May Need to Make Estimated Tax Payments If… Have income that isn’t subject to tax withholding? Or insufficient withholdings? You may have to pay estimated taxes.