You know the old line about the inevitability of death and taxes? It’s still true. What isn’t inevitable, however, is the need to pay penalties to the IRS. It happens, but it doesn’t have to, and the main reason that it does is because taxpayers don’t educate themselves about the rules. When you get hit with an IRS penalty, it adds on to a number that you already wish you didn’t have to pay. To ensure that you get through tax season without unnecessary costs and aggravation, here’s a list of the tax penalties that the IRS most frequently assesses against taxpayers. The 8 Most Common Tax Penalties Assessed Penalty for underpaying estimated tax payments Penalty for taking early withdrawals from tax-advantaged retirement accounts, including IRA accounts and 401(k) accounts Penalty for taking nonqualified withdrawals from 529 plans, health savings accounts (HSAs), and similar tax-favored accounts Penalty for failing to take required minimum distributions (RMDs) from tax-favored retirement accounts Penalty for making excess contributions to IRAs and other tax-favored accounts Penalty for failing to file, or for filing your required tax return after the designated due date Penalty for failing to pay your taxes on time Penalty for filing a substantially incorrect tax return or taking frivolous positions on a return Let’s take a deep dive into each. The more you know, the better you’ll understand how to avoid these mistakes. 1. Penalty for not making estimated tax payments Where does your income come from? If you’re a W-2 employee whose employer withholds your federal income tax on your behalf, then estimated tax payments are not something you need to worry about. On the other hand, if you get income from which withholding isn’t deducted, then you are legally obligated to submit estimated quarterly tax. Failure to do so is subject to penalty. Who has to submit quarterly estimated taxes? You do if you’re a part of the “gig” economy which makes part or all of your income from freelance jobs or independent contracting work, or if you’re a retiree who relies on or derives income from Social Security and your personal savings accounts or other accounts whose withdrawals are taxable (or subject to capital gains). Own a small business? If you’re subject to self-employment tax, then you’re supposed to submit it quarterly. Though this requirement is straightforward, most people start their income journey as W-2 employees: they may have no familiarity with estimated quarterly taxes, or if they do they may not be in the habit of paying it and have forgotten. Whatever the reason, the penalties for failure to make these payments can add up pretty quickly. The government has set up the quarterly payments so that the IRS Form 1040-ES is marked with four dates throughout the year — April 15th, June 15th, September 15th and January 15th (or the next business day if the 15th falls on weekend or legal holiday) of the year that the year’s tax filing is due. In doing so, they have it set up so that the majority of the taxes that are owed are paid throughout the year, though not on a weekly, biweekly or monthly basis the way that W-2 employees withholding is sent in. Failing to send the monies in for each quarter of 2018 is set to be penalized on an annualized basis of 4 to 5 percent. The best way to avoid the penalty is to pay your taxes on the dates that they’re due, calculating the payments accurately enough to represent either 90 (85% for 2018) percent of the actual amount you end up owing or 100% of the amount that was appropriate from the previous tax year. That 100% of the previous year’s amount is acceptable under what is known as safe-harbor, though for those whose income is more than $150,000, the percentage needed is 110% of the previous year’s income tax. Conversely, those who owe less than $1,000 in annual taxes do not get penalized at all. It is important to note that the penalty percentage has jumped to 6 percent as of the first quarter of 2019. 2. Penalty for taking early withdrawals from tax-advantaged retirement accounts, including IRA accounts and 401(k) accounts Having a retirement account is a smart thing to do, and it’s something that the government has encouraged by allowing for the creation of special tax-advantaged vehicles. These tax advantages represent a tremendous incentive and benefit, but they come with strings: until you are 59 ½, you are not permitted to take money out of those accounts prior to retirement without having to have to pay a hefty 10% penalty. As important as it is to know about the penalty so that you don’t take money out hastily and without a full understanding of the impact of doing so, but it’s also important to know when you can take the money out without being penalized. You’re permitted to take out up to $10,000 from and IRA for the purchase of a first home, as well as to pay any uncovered, unreimbursed medical bills that add up to more than ten percent of your adjusted gross income from any retirement plan. If you’ve been out of work and received unemployment compensation for a minimum of 12 weeks, you can take out up to $10,000 from and IRA to pay for your health insurance premiums. Distributions can also be taken from an IRA to pay for qualified higher education expenses, including fees, room and board and of course tuition, all without penalty. And if you’re leaving your job during the same year that you’re turning 55 or older, you can take money out of a 401(k) account from the job that you’re leaving without penalty. The fact that there is no penalty does not negate the income taxes that you would be required to pay on withdrawals from any retirement account.3. Penalty for taking nonqualified withdrawals from 529 plans, health savings accounts (HSAs), and similar tax-favored accounts Just as the government works hard to make sure that the retirement accounts they’ve allowed to be tax-advantaged are used as intended, they take a similar approach to other tax-advantaged accounts, penalizing improper use and withdrawals from 529 plans, health savings accounts, and similar vehicles. 529 plans – These plans provide the ability to set aside funds to pay for the cost of college, and were expanded under the recent tax reform act to also allow for funds to grow tax-free for eligible expenses for K-12 education too. Any money that is deposited into a 529 can be withdrawn without penalty as long as the money is going to pay for tuition, books and similar school-related expenses, but if the money is withdrawn for any other purpose, the withdrawn amount is subject to both income taxes on appreciation and a 10% penalty on the entire distribution. One important thing to note: if you have set up a 529 in one child’s name and wanted to use the monies for another child, that is not subject to penalty as long as you change the beneficiary. The same is true for Coverdell ESAs. Health Savings Accounts (HSAs) – These plans were created to assist with the payment of out-of-pocket healthcare expenses. Money deposited into those accounts can grow to be withdrawn tax free as long as they are used for eligible costs; however, if you’re under the age of 65 and you use any of those funds for nonmedical expenses, the withdrawn amount will be subject to a 20% penalty and will also need to be reported on your tax return as income. 4. Penalty for failing to take required minimum distributions (RMDs) from tax-favored retirement accounts If you are a person who has been dedicated to putting money into your 401(k), your IRA, or another retirement account, then the idea of taking money out before you feel like you need it will just feel wrong. Unfortunately, the government requires that you do so once you hit a certain age. The IRS’ rules say that once you are 70 ½ you have to take what is known as a required minimum distribution, a percentage that is based on a published table that factors in your life expectancy and how much your account holds. As much as you might want to let your money continue to grow, the government wants to limit the amount of tax-deferred growth that each taxpayer can realize and start claiming its portion of the money you’ve been keeping it from taxing: that’s the reason for the requirement. No matter how much you’d prefer not to touch your principal, the IRS takes an aggressive approach to make sure that you do so: the penalty for failure to take the amount out on the government timetable is more than significant – it’s 50% of the amount that you were supposed to take out, and if you don’t take out the right amount then you’re going to have to pay half of whatever you should have taken out but didn’t. The annual deadline is December 31st, though for the first year that you owe you have until April 1st to take the withdrawal. Not only do you have to make sure that you make your payment on time, but you have to calculate it correctly, and that can be somewhat complicated because the amount changes each year as your life expectancy and the value of your account shift. The good news is that the bank or investment company where you’re holding your money is generally equipped to assist with the calculation, and can even make things easier by arranging for automatic dispersals. Setting this up makes a lot of sense, as it eliminates the emotional twinge of writing a check and makes sure that it gets done so you can avoid that draconian penalty. However, the IRS does have the power to waive the penalty if you can show reasonable cause for failing to take the distribution and have a made a corrective distribution before applying for a penalty waiver.