For most people with straightforward finances, doing your own taxes is genuinely easy. Modern tax software walks you through every step with plain-language questions, handles the math automatically, and catches common errors before you file. If your income comes from a regular job and you don’t have complex investments or a business, you can realistically finish in a few hours. The difficulty rises sharply once you add freelance income, rental properties, or multiple investment accounts into the mix.
What Makes a Tax Return “Simple”
The single biggest factor in how easy your taxes will be is where your income comes from. If you work a salaried or hourly job, your employer sends you a W-2 that neatly summarizes everything: wages earned, taxes withheld, retirement contributions. Plugging a W-2 into tax software takes a few minutes, and the software calculates the rest. Add in some bank interest or a standard deduction, and you’re looking at what the tax world calls a “simple return.”
The IRS estimates that nonbusiness taxpayers spend about 8 hours total on their federal return, and that includes recordkeeping and tax planning spread across the year, not just the time sitting at a computer. The actual form completion and submission piece averages around 3 hours. For someone with a single W-2 and no itemized deductions, the real number is often closer to 30 to 60 minutes using modern software.
You’re solidly in DIY territory if your situation looks like this: income from one or two W-2 jobs, maybe some bank interest, the standard deduction, and perhaps a student loan interest deduction or an IRA contribution. Tax software handles all of these without breaking a sweat.
When It Gets Harder
Things change when 1099 forms enter the picture. These forms report income from freelance work, investments, asset sales, retirement distributions, debt cancellation, royalties, and more. There are 21 different types of 1099 forms, and unlike W-2 income, taxes usually aren’t withheld from 1099 payments. That means you need to understand estimated tax payments, self-employment tax, and which deductions you can claim against that income.
Business taxpayers face a much steeper time commitment. The IRS estimates they spend about 21 hours on their returns, with 10 of those hours going to recordkeeping alone. If you’re running a side business or working as an independent contractor, you’ll need to track expenses throughout the year, not just at tax time.
Situations that push the difficulty level up significantly include:
- Rental property income: requires tracking depreciation, repairs, and passive activity rules
- Stock options or equity compensation: involves multiple tax treatments depending on the type of grant and when you sold
- K-1 forms from partnerships or S corporations: these pass through business income and losses that interact with other parts of your return
- Major life events: selling a home, going through a divorce, or inheriting assets each introduce forms and rules that only apply in specific situations
- Multiple state returns: if you earned income in more than one state, each state has its own rules about what gets taxed and what credits apply
Tax software can technically handle all of these, but the software is only as good as the information you feed it. If you don’t know whether a home repair counts as a deductible expense or a capital improvement, the software can’t decide for you.
What Tax Software Actually Does for You
Tax preparation software replaces the old process of reading IRS instructions, filling in paper forms, and doing arithmetic by hand. Instead, you answer questions in plain English (“Did you receive any freelance income?”), enter the numbers from your tax documents, and the software maps everything to the correct forms and schedules. It calculates your tax, applies credits, and tells you whether you owe or are getting a refund.
One genuine advantage of filing electronically through software is error detection. The IRS notes that e-file systems catch common mistakes, like mismatched Social Security numbers, missing signatures, or incorrect bank account details, and reject the return so you can fix it before the IRS processes it. That safety net eliminates some of the most frequent filing errors.
The tradeoff is cost. Free versions of major tax software typically cover only simple returns. If you need to report self-employment income or itemize deductions, you’ll usually need a paid tier, which can run anywhere from $30 to $150 or more depending on the complexity and whether you need state filing.
Free Filing Options
If your adjusted gross income is $89,000 or less, you may qualify for IRS Free File, a partnership between the IRS and private tax software companies that gives you access to guided preparation at no cost. Each participating company sets its own eligibility rules based on factors like age, income level, and state residency, so you may need to check a few options to find one that fits.
For anyone comfortable reading tax forms directly, the IRS also offers Free File Fillable Forms with no income limit. These are essentially digital versions of paper forms with basic calculation support. They work, but they don’t guide you through the process the way commercial software does. This option is best for people who’ve filed before and understand which forms they need.
Active-duty military members and some veterans can use MilTax, a free tool offered through the Department of Defense that covers a federal return and up to three state returns. And if you’d rather have a person help you for free, the Volunteer Income Tax Assistance (VITA) and Tax Counseling for the Elderly (TCE) programs offer in-person preparation at community sites for people who qualify.
Mistakes to Watch For
Even with software catching arithmetic errors, the IRS flags several mistakes that trip up self-filers every year. Filing before all your documents arrive is one of the most common. If you report income from a W-2 that shows up in January but forget about a 1099 from a brokerage that doesn’t arrive until mid-February, your return will be wrong. Wait until you’ve received every document before you start.
Choosing the wrong filing status is another frequent error. If you’re married, you can file jointly or separately, and the difference in tax owed can be substantial. Single filers who support dependents might qualify for head of household status, which offers a larger standard deduction and lower tax rates. Software will ask about your situation, but it relies on you answering accurately.
Data entry errors still happen even with guided software. Entering $54,000 instead of $45,000 in wage income, or transposing digits in a Social Security number, can delay your refund or trigger an IRS notice. Take a few minutes to compare every number on your return against the original documents before you submit.
How to Decide If You Should DIY
Start by counting your tax documents. If you have one or two W-2s, maybe a 1099-INT from a savings account, and you plan to take the standard deduction, doing your own taxes is straightforward and there’s little reason to pay someone else. Budget an hour or two, and you’ll likely be done.
If you have a handful of 1099 forms, some itemized deductions, or a side business with modest expenses, you can still do it yourself, but plan to spend more time. Read the software prompts carefully, keep your receipts organized, and double-check anything that feels unfamiliar. The 8-hour IRS estimate for nonbusiness filers is a reasonable ceiling for this group.
Where self-filing starts to carry real risk is when you’re dealing with situations you genuinely don’t understand. If you received a K-1 form and have no idea what it means, or you sold rental property and aren’t sure how to calculate the gain, the cost of getting it wrong (penalties, interest, or missed deductions worth thousands of dollars) can easily exceed what you’d pay a professional. The question isn’t really whether the software can handle it. It’s whether you can feed it the right information.