I Did My Taxes 2.5 Times This Year So You Wouldn’t Have To

Please make way for a short story of my tax journey before I get into the real meat of why I did my taxes 2 1/2 times this year. There’s a reason, I swear.

Way back when I was a teenager, come tax season my parents took my paltry W2 from my part-time job and had their accountant file my taxes with their more complicated report. Since I had nothing interesting to report – no investments, almost no banking interest, and a minuscule yearly income – their accountant did my taxes for free. Toward the end of college I began filling out the tax paperwork (on paper; yes, this was a thing) myself since, once again, it was fairly straightforward. However, once I moved to a different state for grad school I spent several hours of flipping back and forth between twenty pages of tax forms from my new state of residence and declared that state’s tax forms to have been created by an illiterate toddler; they just didn’t make sense.

From there I took my taxes to a professional tax preparer, but was ultimately dismayed by the fact that even though I was paying the company to file my taxes correctly I had to sign a paper at the end of the session essentially agreeing that the preparer was not liable for submitting my taxes correctly. Wait, what? Is this not your sole job?

Moving on from that experience I tried TurboTax, as it was one of the first and most recommended user-friendly online systems (à la How To Do Taxes For Dummies) in place. TurboTax was also advertised as a free service, but I soon came to realize that every year there was a explanation as to why I couldn’t file for free – one year it was because I had an health savings account (HSA), the next year I filed too late (but still several weeks before the IRS deadline), another year because I made charitable contributions – the list went on. I hate to say that I took me entirely too many years of thinking I would be filing my taxes for free with TurboTax and then being told I had to pay at the very end before I wizened up and looked for another tax preparation service.

Fortunately, a few years ago I discovered that the IRS offers a free file service for those with an adjusted gross income of under $72,000. The services are actually free and backed by the IRS, so they are safe and reputable. I read somewhere that a ridiculously small amount of people who qualify for this service actually use it, which seems like such a shame. Several of the private companies who have partnered with the IRS to provide free federal filing also offer free state filing, depending on where you live. It’s also important to keep in mind that this service is based on adjusted gross income (AGI), not gross income. My AGI wound up being several thousand dollars less than my overall gross income, which means those who make over $72,000 gross may still qualify. If your AGI is more than $72k your other option is to use the free electronic fillable forms available through the IRS for your federal taxes (it doesn’t look like there is an option to file your state taxes for free with the IRS if you make over $72,000). It finally pays to have a low income!

The IRS partners with different companies each year, so when I first started using the IRS Free File System I chose the most well-known company. The whole process went very smoothly and I found the program to be very user-friendly; it had a set-up very similar to TurboTax. Unfortunately this company, H&R Block, did not partner with the IRS for the 2020 tax season, which meant I needed to select a new company off of the IRS Free File Website.

Tax filing attempt #1

I started off with OnLine Taxes (yes, it’s reputable despite its name suggesting otherwise). The site worked fine, but it was significantly less user-friendly than TurboTax and H&R Block. It had the feel of a tax form converted directly into an efile format; I had to enter information line by line, sometimes without explanation as to what was being asked of me. Further, OnLine Taxes asked me to enter in the name, address, and phone number of each of the banks that had issued me a 1099-INT – and I had more than 10 such forms. Why I couldn’t just enter the bank name and employer identification number of each bank is beyond me. Needless to say that when I reached the end of the process and saw my estimated refund was several hundred dollars less than my refunds from past years I was a bit perplexed, and wondered if I had made a mistake. So before hitting submit I decided to double-check my work…

Tax filing attempt #1.5

Since I enjoyed my experience with H&R Block in previous years through the IRS/H&R Block free file public/private partnership I did a bit more digging and found that H&R Block does have free federal and state filing for most individuals for the 2020 tax season, even though they aren’t partnering with the IRS this year. I was excited to read this and quickly I logged into my account and began to file my taxes. Unfortunately, about halfway through I was informed by H&R Block that I didn’t qualify to file for free since I worked as a contractor (ie. was self-employed) by one of my gig jobs and therefore would have to upgrade to their Deluxe package for $50+. Since the whole point of this exercise was to file for free I decided against this. I will hand it to H&R Block that the system notified me as soon as it was determined I would be ineligible to file for free, which I can’t say about all tax preparation services.

Slightly deflated, I did further research and briefly considered Credit Karma Tax, which also sounded sketchy to me but has been endorsed by reputable sources and is a favorite of Purple from A Purple Life. It sounded like a pretty sweet deal since Credit Karma Tax offered free federal and state filing as well as free audit defense. However, after a bit more research I discovered why this offer might merit further consideration – as the saying goes, when the product is free, you are the product. To be clear, I’m not saying you shouldn’t use Credit Karma Tax; I’m simply advocating for a full understanding of what you’re providing to the company in return for doing your taxes for free – which is your data. This differs from the free tax filing programs through the IRS Free File program, as per the IRS:

Tax filing attempt #2.5

After stewing on the above for a bit of time I ultimately decided I didn’t want to sacrifice my information for free tax services, so back I went to the IRS Free File website. This time I did further research to find a more user-friendly program that offered both federal and state filing. I ultimately settled on TaxAct, which I found to be much more user-friendly than OnLine Taxes, although a bit less user-friendly than TurboTax or H&R Block. For example, while TaxAct still asked for my banks’ addresses, they were at least able to auto-generate the city and state after I entered in the zip code.


Even though I filled out my taxes 2 1/2 times this year, I am sad to admit that my 2020 refund is still much lower than previous years. It seemed OnLine Taxes wasn’t too far off with their estimates – this year was different from years past in that I earned a decent amount of money that I hadn’t paid taxes on during the year, such as $1,300 in bank account interest through high-interest savings accounts and bank account hacking, as well as my self-employment income which isn’t taxed during the year, so I was due to pay taxes on this money.

After filing with TaxAct both my federal and state taxes were accepted the same day as filed. My meager federal refund was deposited in my banking account a week later and my state refund was mailed to me via check (why??) about two weeks after I filed.

In other news, the IRS has extended the tax filing deadline to May 17, so now you have even more time to consider all of your tax filing options (what fun!). Have you heard of the IRS Free File program? How did you file your taxes this year?

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