Now accepting new clients for the 2027 tax season.

Retirement Income Tax Preparation

Clear, careful tax preparation for your retirement years.

Retirement income comes from more places than a paycheck did: Social Security, a pension, IRA or 401(k) withdrawals, and sometimes part-time work. Each is taxed its own way. We prepare your individual return so each source is reported correctly and your withholding makes sense.

Check the States We Serve

What we prepare and report

  • Social Security benefits from Form SSA-1099, including working out how much is taxable.
  • Pensions and annuities from Form 1099-R.
  • Traditional and Roth IRA distributions, and 401(k), 403(b), and similar plan distributions.
  • Required minimum distributions and qualified charitable distributions made directly from an IRA.
  • Rollovers and transfers, reported so they aren’t taxed as if you’d cashed out.
  • Withholding and estimated taxes on your retirement income.

Common tax considerations

How much of your Social Security is taxable

Depending on your other income, none of your Social Security benefits, or up to 85% of them, may be taxable. Withdrawals from retirement accounts can push more of your benefits into taxable income.

Required minimum distributions

Most people must start taking RMDs from traditional IRAs and workplace plans at age 73. A missed RMD can bring an additional tax, which can often be reduced when it’s corrected promptly. We’ll check that what you took matches what the 1099-R shows.

Roth and early distributions

Qualified Roth distributions are generally tax-free. Distributions before age 59½ may carry an additional 10% tax unless an exception applies, and Form 1099-R codes don’t always capture the exception. We look at your situation, not just the code.

Rollovers

A direct rollover between accounts isn’t taxable. An indirect rollover must generally be completed within 60 days. The 1099-R will show the distribution either way; we make sure the return shows the rollover.

Withholding and estimated taxes

Retirement income doesn’t always have enough tax withheld. We’ll show you whether you underpaid and what to adjust, through your pension or IRA withholding or estimated payments.

Documents and records to gather

  • Form SSA-1099 (Social Security)
  • Forms 1099-R from pensions, IRAs and plans
  • Records of rollovers or conversions
  • Records of any QCDs you made from an IRA
  • Records of nondeductible IRA contributions (Form 8606)
  • Estimated tax payments you made
  • Any W-2 or self-employment income
  • Last year’s tax return, if you’re new to us
The Square Penny provides tax preparation, not retirement planning or investment advice. We report your income and help you understand the tax on it; we don’t recommend how to invest or when to draw on your accounts.

Related services

You receive a quote after we review your intake and documents.