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If I could give 10 stars I would If I could give 10 stars I would Such an amazing service so needed during the times when EDD almost never picks up Claimyr gets me on the phone with EDD every time without fail faster. A much needed service without Claimyr I would have never received the payment I needed to support me during my postpartum recovery. Thank you so much Claimyr!
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One thing nobody mentioned yet - make sure you're paying quarterly estimated taxes on your 1099 income going forward! If you continue doing this freelance work, you should be making quarterly tax payments to avoid owing a big amount at tax time (and possibly penalties for underpayment). The IRS expects you to pay taxes throughout the year, not just at filing time. Form 1040-ES is what you'll need. It's relatively simple - you estimate your tax liability and make payments four times a year (April, June, September, and January of the following year).
Ugh that sounds like a headache. How do you even know how much to pay each quarter when your income is irregular?
It can definitely be annoying at first, but it gets easier. For irregular income, you have a couple of options. The simplest is to use the "safe harbor" provision - if you pay 100% of your previous year's tax liability (or 110% if your AGI was over $150,000), you won't face underpayment penalties even if you end up owing more. Alternatively, you can estimate each quarter based on actual earnings for that period. I use a simple method - I set aside roughly 30% of each 1099 payment I receive and make my quarterly payment from that. This usually covers both income tax and self-employment tax. If I overpay, I get a refund at filing time. There are also apps like QuickBooks Self-Employed that can track your income and automatically calculate your quarterly payments.
Don't forget about the Qualified Business Income deduction (Section 199A)! If you're filing as a sole proprietor with that 1099-NEC, you might qualify for up to a 20% deduction on your net business income. This is separate from your business expense deductions and could really help reduce what you owe. Also, as others mentioned, make sure you're deducting all eligible business expenses on Schedule C. Even small things add up - software subscriptions, portion of internet/phone, office supplies, professional development, etc. I ended up with over $3k in legit deductions my first year doing freelance work that I almost missed.
I hear so many people talk about home office deductions but I've always been told it's an audit red flag. Is it actually worth claiming?
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Former tax preparer here. We literally wouldn't even bother correcting something this small on a client's return. The IRS has what's called a "de minimis" rule (basically meaning "too small to matter") for exactly this kind of situation. For perspective: the IRS processes over 150 million individual tax returns annually. They don't have the resources to chase down dollar-level discrepancies. If your return is off by a few hundred dollars they might send a letter, but $1.02? Not a chance. Sleep easy and remember this experience next year!
What's the threshold where the IRS actually starts to care? Like, if I forgot to report $100 of income or something, would that trigger any issues?
There's no official published "we care at this amount" threshold, but in practice, the IRS typically doesn't pursue amounts that would change your tax by less than $50. This usually translates to around $200-500 of unreported income for most tax brackets. Remember though, intentionally not reporting income is different from making a small mistake. The best practice is always to report everything accurately, but occasional small errors won't result in any consequences. The IRS computer matching system will usually catch larger discrepancies automatically (like if you forgot to report a W-2 or 1099 that was submitted to them).
Lol when I first started filing my taxes I was exactly like this! I forgot to include a $3 dividend payment and was convinced I was going to jail 😂 Trust me, the IRS doesn't care. I now realize how ridiculous I was being. Actually a tax guy told me once that if you tried to amend for something this small, it would literally cost the government more to process your amended return than any tax they'd collect. Just file correctly next year and move on.
This makes me feel so much better! I've been having literal stress dreams about this tiny amount. Next year I'll be sure to double check all my investment accounts before filing!
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I work in customer support (not for H&R Block), and I can tell you that creating a new account is totally fine. Companies expect people to make multiple accounts for various reasons. The only potential issue is if you're in the middle of a filing that has saved data - that won't transfer to your new account.
Would the IRS care if I filed with a different email than last year? Does that information even get sent to them?
The IRS doesn't receive or care about what email address you used to file your taxes. They're only concerned with the actual tax information (SSN, income, deductions, etc.), not the account details from the tax preparation software. When you e-file, the only things transmitted to the IRS are your tax forms and the data they contain, along with some tracking information from the tax preparation company. Your login credentials, email address, and account information stay with the tax preparation company and aren't part of what gets sent to the IRS.
Have you tried calling H&R Block directly? Sometimes they can remove premium if you explain the situation. I accidentally upgraded to premium last year and they switched me back when I called.
Their customer service is the WORST. I tried calling about a similar issue and was on hold for 1.5 hours before I gave up. Their chat support just sends automated responses that don't address the issue.
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This exact thing happened to me and my husband! It's SO frustrating how unclear the W-4 is. One thing nobody mentioned here yet - you can also just specify an additional dollar amount to withhold on line 4(c) of the W-4. For us, we calculated that we were underwithholding by about $400/month total, so we each put an extra $200 per month on line 4(c). So every paycheck (we get paid biweekly), we have an extra $92 withheld. You might want to also look at your state withholding forms too. We were underwithholding at both federal and state levels.
Thank you for this suggestion! Do you know if there's an easy way to calculate exactly how much extra we should withhold? I'm worried about overwithholding too much and giving the government an interest-free loan, but obviously don't want another tax bill shock.
The most straightforward way to calculate your additional withholding is to take the amount you owed this year ($3900), add any expected income increases for next year, and divide by the number of pay periods remaining in the year. For example, if you both get paid twice a month (24 pay periods per year), and you start in April with 18 pay periods remaining, you'd need approximately $217 additional withholding per pay period ($3900 ÷ 18). You could split this between your W-4s. If you're concerned about overwithholding, you can be a bit more conservative with the extra amount. Remember you can always submit a new W-4 partway through the year if you find you're still not withholding enough.
Everyone is making this more complicated than it needs to be. Just go back to withholding at the Single rate. That's what my wife and I do. We both select "Married but withhold at higher Single rate" and we get a small refund every year. The "Married" withholding rate assumes your spouse doesn't work or makes very little. So when both spouses work and make similar amounts, you're going to drastically underwithhold if you both select just "Married.
This is the correct answer! My wife and I both make around $100k and we've always used "Married but withhold at higher Single rate" without any issues. The regular "Married" option only works if one spouse doesn't work or makes significantly less.
Mason Lopez
FYI - for anyone using FreeTaxUSA for crypto reporting, look for the "Capital Gains" section, then select "I'll enter my transactions manually" when it asks about your 1099-B forms. You can then enter each transaction with the date acquired, date sold, proceeds, and cost basis from your CSV file. Make sure you classify them correctly as short-term or long-term! That's a common mistake people make and it can significantly impact your tax situation. Short-term is for anything held less than a year and is taxed at your normal income rate.
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Gemma Andrews
•Thanks! Is there a way to attach the CSV file directly or do I have to manually type each transaction? I have about 74 trades to report from last year.
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Mason Lopez
•Unfortunately FreeTaxUSA doesn't have a direct CSV import feature for crypto transactions. You'll need to enter them manually if you're not using a third-party tool like some others mentioned. If you have a lot of transactions, you might want to consolidate them by date if they're similar (like multiple small trades on the same day with the same cryptocurrency). FreeTaxUSA has a "Form 8949" checkbox that lets you indicate you're reporting summary information rather than each individual trade. Just make sure your totals are accurate.
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Vera Visnjic
Quick warning from someone who learned the hard way - don't skip reporting your crypto even with losses and no 1099-B. I thought since I lost money and received no forms, I didn't need to report anything last year. The exchange ended up sending information to the IRS later and I got a CP2000 letter about unreported transactions. Had to file an amended return and pay interest on the difference (though in my case it was actually a refund since reporting the losses properly reduced my tax bill).
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Jake Sinclair
•What information did the exchange send if they didn't give you a 1099-B? I thought smaller exchanges weren't required to report?
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