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World of Software > News > How H&R Block Helps Freelancers and Gig Workers Stay Ahead of Tax Season
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How H&R Block Helps Freelancers and Gig Workers Stay Ahead of Tax Season

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Last updated: 2026/01/21 at 4:15 AM
News Room Published 21 January 2026
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How H&R Block Helps Freelancers and Gig Workers Stay Ahead of Tax Season
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Freelance work comes with many benefits, but it can make tax season feel tricky. As a freelancer, you don’t have an employer withholding taxes from your paycheck each pay period, and you’re responsible for tracking your income and figuring out your deductible expenses which can vary widely depending on your line of work and other factors. You also have to calculate your quarterly estimated federal and state tax payments, including self-employment tax.

Add in tax rules that can change from year to year, and it’s easy to see why tax season can feel overwhelming for self-employed workers. H&R Block provides options for freelancers and gig workers who need to be prepared for tax season year-round, not just when the filing deadline approaches.

Tax filing tools designed for freelancers and gig workers

Finding the right tax filing solution is especially important for freelancers and gig workers whose income doesn’t fit neatly into a single category. H&R Block Self-Employed is designed to accommodate multiple income sources within a single return, which can be useful for people who get paid by more than one employer, platform or client.

Whether you’re driving for Uber or juggling multiple freelance clients, the software walks you through reporting your income from each source. It’s intuitive, easy to use and up to date with the latest tax rules and regulations. For freelancers and gig workers who earn income through platforms like Uber, DoorDash or Instacart, H&R Block Self-Employed is built to handle self-employed filing in one place.

Simplifying income tracking with 1099 import tools

One of the most tedious aspects of taxes for freelancers is gathering and entering information from multiple 1099 forms. Not only is this process time-consuming, but manually entering that information increases the likelihood of mistakes.

That’s why H&R Block Self-Employed allows users to import 1099s directly into their tax return, however they receive them. The platform offers smart import tools and PDF upload options for common freelance tax forms that give you options, including:

  • Upload PDFs directly: If you’re provided with a form like a 1099-NEC as a PDF, H&R Block’s platform extracts the information for you.
  • Upload a photo via the H&R Block app: If you received printed copies of your forms, use the H&R Block app to snap a photo and quickly import your form.

For freelancers juggling income from several sources, this can save time and reduce stress during tax season. By pulling income details directly into the return, you can move forward knowing your income is accurately accounted for.

Note that you’re responsible for reporting all of your freelance income whether or not you receive a 1099 form, and H&R Block Self-Employed can also guide you through proper reporting without a form.

Finding and claiming the right deductions for your work

Freelancers and gig workers can deduct business-related expenses, but it can be hard to know which expenses qualify. In general, the IRS allows self-employed filers to deduct expenses that are considered “ordinary and necessary” for the work they do. What falls into that category depends on how you earn your income.

What kind of expenses can you deduct?

H&R Block Self-Employed guides freelancers through this process by asking questions about their work and expenses and helping them determine which deductions might apply to their specific situation.

  • Uber, Doordash and Instacart Drivers: Rideshare and delivery drivers may be able to deduct mileage and certain vehicle-related expenses.
  • Digital Creators: Creators may be able to deduct the cost of video equipment, lighting or editing software used for content creation.

Can you deduct home office expenses?

If you use part of your home regularly and exclusively for business, you may be able to deduct home office expenses from your taxable income. With H&R Block Self-Employed, you don’t have to understand complex tax rules or calculate percentages, you just answer a few simple questions to determine whether you can deduct home office expenses and how much.

Support options when self-employed taxes get complicated

Even with the right software, filing your taxes as a freelancer can get complicated, especially if you’re unsure how to handle certain expenses, income types or deductions. That’s where additional support options can make all the difference. H&R Block Self-Employed includes access to:

  • AI Tax Assist lets you get instant answers to common questions like which forms are required for your specific situation.
  • Expert chat connects you to a live tax professional when you need guidance but don’t want to fully hand off your return to another person.

Instead of guessing, you can ask questions and get clarification as you file.

An affordable option for self-employed taxes

When choosing tax software, freelancers often compare costs as well as features. And with H&R Block’s Maximum Refund Guarantee, you have the piece of mind of knowing you’re getting every cent back that you can. If you discover an error that entitles you to a larger refund or smaller liability, H&R Block will refund the fees you paid for your tax prep and allow you amend that return for no additional charge.

Why H&R Block is best tax filing option for freelancers and gig workers

Freelancers face unique tax challenges, from managing multiple income streams to identifying eligible deductions. That’s why many self-employed individuals choose H&R Block, which offers the best tools and support for gig workers and full-time freelancers, including:

  • Smart easy-import tools for multiple income sources, unlike major competitors
  • Guidance on deducting business expenses for your type of work, from delivery and rideshare drivers to digital content creators to other types of freelancers
  • Robust support with AI Assist and expert live chat to answer questions as you file

Freelance work can make tax season stressful, but H&R Block Self-Employed gives you flexible, specialized tools that fit the way you earn your income and support you along the way.

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