Will you Be Penalized for Under Withholding Taxes?

by | Mar 24, 2020

MA DOR – Letter of Assessment

Heads Up! We have learned that the MA DOR seems to be actively sending out more of their Letters of Assessment. This could be Covid related since the state is not bringing in as much tax revenue as forecasted. Regardless, you need to be aware that if you owe the state...

IRS Notice 1444 (EIP)

Keep Your 2020 Economic Impact Payment notice with other tax records   People who received an Economic Impact Payment this year (2020) should keep Notice 1444, Your Economic Impact Payment, with their tax records. This notice provides information about the amount...

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Covid-19 Distributions

If the Caronavirus has had negative effects on your finances, temporary changes to the rules under the CARES Act may give you more flexibility to make an emergency withdrawal from tax-deferred retirement accounts during 2020. 

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Going Alone to Medical Appointments May Be Dangerous to Your Health?   Here’s a chapter out of Anne’s relationship with Joe and Elaine of Pinehills Tax Services and ardent believers in Seniors Helping Seniors! If you would like to read the back story on our...
Many taxpayers have gone from receiving a large refund in 2018 to owing the IRS more than $1,000 on their 2019 returns! Did you know the IRS can penalize you for Failure to pay proper estimated tax. If this is you, here’s some food for thought.


  • The IRS can charge you a penalty if you owe them $1,000.00 or more for under withholding taxes. This penalty was waived for 2018 but may not be for 2019. I know how we hate to research questions on the IRS website but here’s a link to Common Penalties to Individuals.
  • The Quick Fix: You can quickly remedy this situation by having extra taxes taken out of your paycheck. Assuming that your income will not change significantly during 2020. You can divide the amount you owe the IRS by the number of pay periods left in the year to determine the “extra” withholding amount per pay period. Then contact your payroll department and have them take that amount from your paycheck as “extra” federal tax withholding.
  • The More Accurate WaySubmit a new W-4. Go to the IRS website and use their tax withholding estimator to figure out what you should be withholding. However, you will need to adjust this amount for the number of pay periods remaining in the current year.
  • Another More Accurate Way. Prepare a “faux” tax return for 2020 and make sure that you are withholding the tax due calculated on your faux return from your paycheck on an annual basis. However, you will need to adjust this amount for the number of pay periods remaining in the current year.

Our Recommendation for 2020

Assuming that your income will not increase significantly in 2020, use the Quick Fix. It should get you under the $1,000 limit and put you within acceptable IRS limits for paying estimated taxes.


Our Recommendation for 2021

Complete a new W-4 to have a more exact tax withholding from your paycheck.


The Ultimate Solution

Because your tax situation is unique to you, consult with your tax preparer or advisor. S/he should be able to help you determine the best strategy for paying your estimated taxes.