Tax deadlines, penalties and estimated payments — everything you need to know

At Waldman Accounting, we help W2 employees, independent contractors, small business owners, real estate investors, entertainment clients and more navigate their taxes. Whether you stress over estimated taxes or organizing your finances to hit the April 15th tax deadline, we’re here to give you confidence and peace of mind each tax season. The following are topics we frequently cover with clients.

Tax Deadlines Explained

The federal tax filing deadline for individuals is April 15 — or the next business day if it falls on a weekend or holiday. Partnerships and S-Corps must file their tax returns (Form 1120) by March 15th unless they operate on a fiscal year.

Filing Your Tax Return

Your tax return is due by April 15 unless you request an extension.

Making Tax Payments

If you owe taxes, the payment is also due by April 15 — even if you file for an extension. If you don’t pay by this date, you may face penalties and interest on the unpaid amount. 

Extensions

Filing a tax extension gives you more time to file your return — typically until October 15. It is important to note: an extension gives you more time to file your paperwork but does not give you more time to pay your taxes. If you think you’ll owe taxes, you should estimate the amount and pay it by April 15 to avoid penalties and interest.

What you need to know about making estimated tax payments

Estimated taxes are periodic payments made to the IRS throughout the year to cover income not subject to withholding, such as:

  • Self-employment income
  • Rental income
  • Interest and dividends
  • Capital gains

If you’re not sure whether you’ll owe taxes or how much, it’s better to err on the side of caution and make an estimated payment. You can use your previous year’s tax return as a guide to estimate what you might owe.

Tip: The IRS allows for a refund if you overpay, so sending an estimated payment now can save you from penalties, and you’ll get the excess back when you file.

If you have no idea where to start, we can help you calculate a reasonable estimate to avoid underpayment penalties.

Estimated tax payment example

John isn’t sure if he’ll owe taxes this year, but he knows he earned more than last year. Based on his 2023 return, he estimates he might owe $3,000 and pays that amount by April 15. When he files his return, he finds out he only owed $2,500 and gets a $500 refund.

How to avoid penalties

If you opt to pay estimated taxes each quarter, payments are due each quarter with a specific payment due date.

Pay periodEstimated taxes due date
January 1 – March 31April 15
April 1 – May 31June 15
June 1 – August 31September 15
September 1 – December 31January 15 of the following year

If you don’t pay estimated taxes or do not file and pay by the tax deadline, penalties for late estimated tax payments are the following:

  • For $1,250 of income or more: 2% of total
  • For $1,250 of income or less: $25

For non-W2 employees, independent contractors or folks with a side hustle, it might make sense to hold and pay all your taxes by the filing deadline. However, if you know yourself, and you don’t have the discipline to set aside 30% for taxes only, you may want to consider paying estimated taxes throughout the year.

How to pay estimated taxes

Payments can be made electronically through the IRS’s online portal, by mail using payment vouchers, or through other approved payment methods.

Staying ahead of tax deadlines — by making timely payments or filing an extension — can save you money and reduce stress. If you’re unsure, Waldman Accounting will help you figure out the best approach.

Have questions? Talk to our experts.

Phone

954-347-9647

Email

ianwaldman@waldmanaccounting.com

Address

Ft. Lauderdale, Florida