Please see Publication 915 at https://www.irs.gov/pub/irs-pdf/p915.pdf. Page 3 explains the taxability of your benefits. Page 3 explains the taxability of your benefits and there are worksheet you can use to calculate any taxable amount.
There is a Social Security Benefits calculator at ssa.gov/OACT/quickcalc/ that will show you how much you may be entitled to, and the change in amount if you choose to take your benefits early. There are also links on that page if you scroll down to the "Related Information" section that may help you decide your "when and if" questions.
You can also go to our website: https://turbotax.intuit.com/ and click on the Resources tab to find our calculators. Our TaxCaster Tax Calculator can help you determine your tax liability when you include SSA payments on the return. You may want to consider whether or not you will still be earning income when you begin to draw your SSA as your total income will affect the percent of your Social Security that will be subject to tax.
