Gig Workers Save 20% With H&R Block

March 21, 2025

H&R Block Review for Gig Workers

As tax season looms over us, we want to make sure gig workers are prepared.

Hopefully, you’ve been tracking your mileage and business expenses throughout the year, so you can take advantage of all deductions related to your rideshare or delivery driving gigs. H&R Block is prepared to help you file properly.

You don’t have to spend a fortune or try to muddle through taxes on your own, especially when juggling multiple income streams. H&R Block has resources available to you, and tax professionals are ready to help you.

For gig workers, they even offer a 20% discount when you file with H&R Block Online. Plus, they let you know what you’ll owe upfront, so you won’t get a sticker shock at the end when you’re ready to file.

H&R Block is filled with tax experts and has been a great resource for all your tax needs for the past 70 years, serving more than 20 million working Americans each year. They keep track of all the tax rules, which seem to change often, so you can be assured you’re following the law and getting things done on time and correctly.

As you may or may not know, independent contractors such as freelancers and gig workers file additional tax forms compared to W-2 employees. H&R Block’s DIY tools help with self-employment-related tax deductions such as mileage, qualified business income, and health insurance premiums, all designed to lower your taxable income.

Online Support for Gig Workers

Remember, as a gig worker, you are generally considered a small business owner. H&R Block offers two options geared toward freelancers, independent contractors and gig workers:

  • Block Advisors: This tier provides comprehensive services with certified small business tax professionals, helping with tax preparation, business formation, bookkeeping, payroll, and other business-related services year-round.

  • DIY Online Self-Employed: This service is a do-it-yourself option that is tailored to self-employed individuals, including gig workers, freelancers, and contractors. It helps you track and deduct your ongoing business expenses, calculates your self-employment taxes, and manages other self-employment-related tasks.

Even if rideshare driving or delivering is your side gig, they can help you file. Personally, I do a mix of W-2 and freelance work. If you’re not sure what your best option is for filing, they have a Help Me Choose feature that will help you decide which plan covers all areas of your tax needs.

Bringing AI Into the Equation

In keeping up with the ever-changing technology, H&R Block has an AI Tax Assist that gives you unlimited tax help 24/7. If you’re going the DIY route, you can ask specific questions concerning the tax law and how it applies to you, and AI Tax Assist will give you instant answers without having to navigate away from the page you’re working on.

AI Tax Assist is powered by Microsoft’s Azure OpenAI, and it utilizes the tax expertise of a team of H&R Block CPAs, tax attorneys and Enrolled Agents in The Tax Institute who interpret the state and federal tax laws and rules and then program the technology to be able to communicate this information in an accessible way to you.

As you’re working through your forms, you can pull up the AI Tax Assist, available in the Help Center, and either pick from a sample question or write your own. It can help you in a variety of ways, including:

  • Answering questions about the tax forms, deductions and credits available to you.

  • Defining tax terms and giving you guidance on specific rules to help you navigate the federal and state tax systems.

  • Giving you information about taxes and recently changed laws and policies. It can even help you check for refund changes from year to year.

  • Providing audit support and helping you understand any IRS letters you’ve received.

  • And, of course, it will help you understand the H&R Block products you’re using in filing.

Live Support

More than just AI Tax Assist is available to you as you’re filing. All paid products will give you access to expert help, both AI and real humans. Live tax professionals are available to help you from 8 a.m. to 9 p.m. CST Monday through Friday (7 days a week during tax season). Find live support in the Help Center.

If you’d rather, you can find an office where a tax professional will prepare your taxes in person.

How To Use H&R Block

Once you choose which way you want to file, you’ll be walked step-by-step through the filing process on H&R Block’s website or app, or the tax preparer will help you in person. You’ll, of course, need all of your tax information from 2024.

This can include any W-2s, 1099s, forms from any interest you paid for your mortgage or student loans, etc. All of these forms should have been mailed to you physically, or you can download them from the sites where you’d usually access your accounts related to them.

For instance, my student loan interest information was found on my student loan portal, where I send in my payments every month.

The process itself is super straightforward and easy to walk through. First, you’ll create an account with H&R Block, provide your email address and phone number, and create a password. You can start with whatever tier you think suits you best, but if you need to change as you go, you’re welcome to bump up to the next level.

From there, you get started! I chose to skip uploading my last year’s taxes at the beginning because I couldn’t find my digital version and didn’t feel like scanning page by page. So, your views may look a little different, but here’s an idea of what you’ll be seeing.

As you can see, at the top right, you’ll see what your expected refund amount will be as you move along in the process. It’ll show a positive or negative balance depending on whether you’ll receive a refund or if you’ll owe money.

On the next panel, you’ll enter your personal information and agree to their consent forms (you are able to download these); then, you’re ready to get started.

You can choose to upload PDFs of your tax forms, or you can enter the information manually. It may not always grab all of the information when you choose to upload, so be sure to review the information carefully before you move on to the next step.

It’ll start you off with your Federal returns and then move on to your State return (if needed). The State return is easy to go through because they transfer any necessary information from your Federal to State, saving you time.

You start at the lowest level offered by H&R Block, but as you enter your information, they will tell you if you need to move up a tier and give you full insight into that cost difference. You will not be charged anything until you’re ready to complete your filing.

What Are My Options for Filing My Taxes?

DIY

File taxes on your own, but never alone. You can file on your own, online, at any time, and on any device. H&R Block’s DIY Online option includes AI Tax Assist and Live Tax Pro Support at no additional cost. Depending on your needs, you’ve got tiers such as Deluxe, Premium or Self-Employed.

File Your Taxes With Expert Help

You can still file online with this option, and you can get the help of an expert throughout the process. This option is made for more complex tax situations and is a great option for deductions, investors, and self-employed gig workers.

Let a Tax Pro File for You

With this option, you can choose whether to file online, in person, or a hybrid solution of the two. This option will put you in contact with a professional. You can choose the same one you’ve used in the past if you’re an H&R Block client already, or you can choose a new one.

Pros and Cons of H&R Block

Pros

  • Customers boast that they prefer using H&R Block to file everything on their own. Having the tools and resources available to answer questions along the way helps with peace of mind.

  • The forms are easy to follow, and there are many prompts to help ensure you’re getting all available deductions and filing properly for your individualized situation.

  • Transitioning from filing on your own or with a different tax professional to H&R Block is smooth and easy. You can even quickly file on the last day that taxes are due.

  • Customer service is informative and easy to work with.

Cons

  • It’s rare, but there are times when the system is offline, making it difficult for customers to file.

  • There are more complex scenarios that their prompts don’t seem to cover, and it’s harder to figure out what exactly you need to do in those situations. However, utilizing AI Assist and their Tax Pros could help with those issues.

  • The cost may be considered expensive to some filers.

FAQs

I’ve Never Filed With H&R Block. Can I Switch From How I’ve Done It in the Past to H&R Block?

Yes! Switching is easy and takes about 2 minutes to do. Just upload a PDF of last year’s tax returns, and your data will automatically be imported.

What Do I Need to File?

H&R Block has a tax prep checklist you can use, or you can create your own so you know you’re covering all your bases.

How Much Will I Get Back or Owe?

This, of course, varies by individual. But H&R Block does have a Tax Refund Estimator you can use to estimate how much you’ll receive back or how much you might owe for your federal taxes.

Why Should I Choose H&R Block?

H&R Block has worked with people just like you, with the same income types and the same questions you have. Their 70 years of expertise will help you with any questions you have and ensure the process is seamless.

They give you upfront pricing, so you know what to expect every step of the way. Even if you want to file on your own, you can utilize their resources to make sure you’re getting the biggest refund possible.

Remember, if you file online, H&R Block is offering 20% off to side hustlers like you.

Did someone forward you this newsletter? Subscribe now for free so you never miss an update…

Never miss a Rideshare Guy update…