IRS and New York State Estimated Tax Payment FAQs

By Charles Rosselli, Tax Attorney


The failure to make IRS or New York State estimated tax payments during the course of the year could be a reason why you owe back taxes to the IRS or NY when you file your income tax returns. 

Many business owners and individuals who receive 1099 income are extremely frustrated with the amount of income taxes they currently pay.

For most individuals,  income taxes are taken out of your paycheck each pay period.

However, for those people who work on commission; who are self employed; or receive certain types of income, tax withholdings are not automatically done.  

You may be responsible to estimate and pay the tax yourself.

Most self employed or small business owners either try to do their taxes themselves or they have a preparer who doesn’t claim all available deductions.

 Many businesses are also set up incorrectly or in a way that is not beneficial to the taxpayer, which also leads to you owing more in taxes each year.

This article addresses what you need to know about estimated taxes and how to avoid getting into the hot water with the IRS or NY State. 

What are Estimated Taxes

You are required to pay taxes on the income that you earn as it is earned.  

The amount of income tax that your employer withholds from your paycheck depends upon the amount that you earn in each payroll tax period and the information that you give your employer on form W-4.

For example, if you have a job, you are typically a W2 employee. Your employer will withhold income taxes from your paycheck and remit those taxes to the IRS and State when you are paid. 

The IRS requires that the tax be paid  when the income is earned, not when your income tax return is due.

This is typically not a problem if you are W2 employee because income taxes are withheld for your paycheck. 

However, if you are self employed;  have business income; or receive rent payments, there are no income tax withholdings.

The IRS requires that you pay tax on income that is not subject to withholding tax on a quarterly basis. Certain states, like New York, have the same requirements. 

Estimated Tax Payment Requirements

Estimated tax payments will need to made by anyone whose income taxes are not withheld from their income or wages. 

There are 3 typical situations where estimated tax payments will need to be made:

  1. For most independent contractors, self employed individuals, or small business owners, income taxes are not deducted from your income taxes. You will be expected to make estimated tax payments if you will owe more than $1000 for the year. 

  2. If you are a partner in a business or shareholder in a corporation, you will likely need to make estimated tax payments. If you are shareholder of a corporation, you will need to make estimated tax payments if the business is going to owe at least $500 in taxes.

  3. If you owed more than $1000 to the IRS last year when you filed your income tax return, the IRS requires that you have more withheld from your paycheck or make estimated tax payments in the following year.

    Waiting to April of next year to pay what you owe when you file your taxes is a “no-no” for the IRS and the State if you fall in one of these three categories.  

The reason why is because most people spend what they earn. The taxing authority knows that most taxpayers will not have the funds to pay the taxes due in one large payment since there were no taxes paid during the course of the year.

For example, if you are a commissioned real estate salesperson and your earn a commission of $5000, you will receive a check for $5000. There were no income tax withholdings from the commission check.

As such, you will be personally responsible for making your quarterly estimated tax payments to the IRS as well as the State ( if the state in which you reside has income taxes).  

Failure to make estimated tax payments may result in owing back taxes to the IRS or State as well as underpayment penalties.

The good news is that estimated tax payments allow you to budget your potential income tax liability with your business and living expenses on a quarterly basis.

How Much Should I Pay

The simplest method to determine your federal and NYS estimated tax payments for this year is to review your last year’s income tax return.

The safest strategy is to pay 100% of last year’s tax liability equally over the four required due dates ( see below for estimated tax due dates).If you will earn less this year then last year, you can pay 90% of last year’s tax liability on a quarterly basis. A more detailed analysis can be made by reviewing your current income , expenses, and income tax rates.

Estimated Tax Payments Due Dates

  • January 1- March 31 : Deadline is April 15
  • April 1- May 31: Deadline is June 16
  • June 1- August 31- Deadline is September 15
  • September 1- December 31- Deadline is January 15 ( of the following year)

New York State Estimated Taxes

To avoid a penalty for the underpayment of taxes to NYS, your payments must be made on time and the total amount of your New York State payment must be at least 90% of the amount of tax shown on your current income tax return or 100% of your last year’s tax return.

The NYS estimated tax due dates are the same as the IRS ( please see above). For a detailed explanation of estimated tax payments for New York State, see publication It-2015-I.

You will be required to make estimated tax payments to New York State if you expect to owe at least $300 of either New York State or NYC tax.

As discussed above, you will need to make estimated tax payments if you fall in one of above categories of being self employed; a small business owner; or a shareholder in a corporation.

Underpayment Tax Penalties

If you do not make your quarterly estimated tax payments, you may owe the IRS or State back taxes as well as underpayment tax penalties when you file your income tax return.

To calculate your underpayment penalty for the IRS, you can go to Form 2210. 

To avoid owing back taxes as well as  estimated tax penalties, follow these four estimated tax tips:

Estimated Tax Tip #1 : If you are a commissioned salesperson, calculate your approximate estimated taxes on each commission check that you receive.

You should set up a separate bank account and immediately put your estimated taxes in that separate account so that when your quarterly payment is due, it is available for payment.

Estimated Tax Tip #2 : It is important to submit your quarterly estimated taxes on time.

However, if you miss a payment, make it as soon as possible.

Don’t wait until the next quarterly payment is due.

Estimated Tax Tip # 3 : If you don’t have the exact amount that is due for the quarter, make as much of an estimated tax payment as you can.

Estimated Tax Tip #4:  Have your accountant or tax preparer calculate your estimated tax payments for the following year.

Your tax preparer should give your four slips of paper with the amount of estimated tax due for each quarter; what to write on the check; and where to mail the estimated tax payments. 

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