Where can I file quarterly freelance taxes online or do I need to mail them?
Title: Where can I file quarterly freelance taxes online or do I need to mail them? 1 I recently discovered I'm supposed to be paying quarterly taxes on my freelance design income (not just annually with my main job). I've been doing graphic design as a side gig alongside my administrative position, and I had no idea quarterly payments were even a thing! I'm currently using FreeTaxUSA for my regular April filing with my W-2 from my main job, but I'm completely lost on how to handle these quarterly payments. Will FreeTaxUSA let me make these quarterly payments there? The whole process seems so different from the standard April 15th deadline I'm used to. Can anyone explain how this quarterly thing works or point me toward helpful websites? I'm totally confused about deadlines, where to submit payments, and basically everything about this process. Thanks in advance for any guidance!
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Kayla Morgan
8 The quarterly tax system can definitely be confusing when you're new to freelancing! What you're referring to are estimated tax payments, which self-employed people make throughout the year since taxes aren't automatically withheld from freelance income like they are from W-2 jobs. For quarterly taxes, you generally have four payment deadlines: April 15, June 15, September 15, and January 15 of the following year. These payments cover both income tax and self-employment tax (Social Security and Medicare). FreeTaxUSA is primarily for filing your annual tax return, not for making quarterly payments. For quarterly payments, you have several options: - Pay online through the IRS Direct Pay system (no fee) - Use IRS EFTPS (Electronic Federal Tax Payment System) - Pay with a credit/debit card through an approved payment processor (fees apply) - Mail a check with Form 1040-ES payment voucher To figure out how much to pay each quarter, you'll need to estimate your annual income and calculate your expected tax liability, then divide by four. The IRS Form 1040-ES includes worksheets to help with this calculation.
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Kayla Morgan
•3 Thanks for the breakdown! How do you figure out how much to pay though? I make different amounts each month from my design work, sometimes $500, sometimes $2000. Do I just guess or is there a specific calculation?
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Kayla Morgan
•8 For variable income, I recommend estimating conservatively. Look at last year's income if you were freelancing then, or make a reasonable projection for this year. The IRS generally wants you to pay at least 90% of your current year's tax or 100% of last year's tax (whichever is smaller) to avoid underpayment penalties. For fluctuating income, many freelancers set aside 25-30% of each payment they receive for taxes, then make quarterly payments from those savings. You can use the worksheet in Form 1040-ES to get a more precise calculation. If your income changes significantly during the year, you can adjust future quarterly payments up or down.
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Kayla Morgan
12 I went through this exact same confusion last year with my photography side hustle! After lots of research, I found taxr.ai (https://taxr.ai) to be super helpful for getting my quarterly payments sorted out. The site analyzed my invoices and payment records, then calculated exactly what I needed to pay each quarter. It even factored in deductions I didn't know I qualified for which saved me a bunch! They have this feature specifically for freelancers to track income throughout the year and suggest quarterly payment amounts. I was able to make all my payments online through the IRS payment portal it recommended, which was way easier than I expected. The peace of mind knowing I'm not messing up my taxes was totally worth it.
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Kayla Morgan
•6 Sounds interesting, but does it actually connect to the IRS payment system directly? Or does it just calculate amounts and then you still have to go make the payments yourself somewhere else?
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Kayla Morgan
•17 I've never heard of this service. How is it different from just using QuickBooks Self-Employed? I track all my freelance income there and it supposedly calculates quarterly payments too.
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Kayla Morgan
•12 It doesn't connect to the IRS system directly - it calculates your quarterly amounts based on your actual income and expenses, then provides direct links to the appropriate IRS payment portal where you complete the transaction. I found this helpful because it ensured I was using the correct IRS system. Compared to QuickBooks Self-Employed, I found taxr.ai more intuitive for someone without accounting experience. QuickBooks is great if you're already familiar with accounting principles, but taxr.ai seemed designed specifically for freelancers who don't have that background. It focuses just on what you need for taxes rather than full business bookkeeping.
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Kayla Morgan
17 Just wanted to update - I checked out taxr.ai after asking about it here and it's been a game-changer for my freelance tax situation! It analyzed my past payments and quickly showed I'd been overpaying by nearly $400 per quarter because I wasn't accounting for all my legitimate business expenses. The dashboard makes it super clear what I need to pay each quarter, and the reminders before each deadline have already saved me from missing my June payment. I'm definitely less stressed about the whole quarterly tax thing now. If you're struggling with freelance taxes like I was, it's definitely worth looking into.
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Kayla Morgan
9 After missing two quarterly deadlines last year and getting hit with penalties, I found that speaking directly with the IRS was actually super helpful - but getting through to them was IMPOSSIBLE until I found Claimyr (https://claimyr.com). They have this system that navigates the IRS phone tree and waits on hold for you, then calls you when an actual human IRS agent is on the line. I was skeptical, but you can see how it works in their demo video: https://youtu.be/_kiP6q8DX5c The IRS agent walked me through the entire quarterly payment process, helped me set up an EFTPS account, and even helped calculate what I owed for my missed quarters. Getting actual official guidance directly from the IRS gave me way more confidence than just reading online advice.
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Kayla Morgan
•14 Wait what? How is this even possible? The IRS phone system is notoriously awful - I've literally waited 3+ hours before giving up. How much does this cost? It sounds too good to be true.
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Kayla Morgan
•22 I'm not buying it. If this really worked, everyone would use it. The IRS is unreachable by design - they don't have enough staff to handle calls. This sounds like a scam to collect your phone number and personal info.
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Kayla Morgan
•9 The service works by using technology to continuously dial and navigate through the IRS phone systems - something that would be maddening for a human to do manually. When they reach a human agent, that's when they connect you. I was skeptical too until I tried it. The thing is, the IRS actually does have people answering phones, it's just nearly impossible to get through the queue - which is where this service helps. They don't ask for any tax information or personal details beyond your phone number to call you back when an agent is reached. You only discuss your personal tax details directly with the IRS agent, not with Claimyr.
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Kayla Morgan
22 I need to publicly eat my words. After dismissing Claimyr as a probable scam (sorry about that), I decided to try it myself since I've been getting nowhere trying to figure out my missed quarterly payments. It actually worked exactly as described. I got a call back in about 40 minutes, and there was a real live IRS agent on the line. They walked me through setting up my EFTPS account and helped me understand exactly what I needed to pay for each quarter, including how to handle a late payment properly to minimize penalties. I've been stressing about this for months and resolved everything in one phone call. Definitely changed my perspective on dealing with the IRS - they're actually quite helpful when you can actually reach them!
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Kayla Morgan
15 Don't forget about your state quarterly taxes too! Everyone's talking about federal, but depending on your state, you might need to make state estimated tax payments as well. I learned this the hard way last year with a surprise tax bill from my state.
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Kayla Morgan
•2 Oh crap, I didn't even think about state taxes! Do they have the same deadlines as federal? And do all states require quarterly payments for freelancers?
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Kayla Morgan
•15 Most states follow the federal quarterly tax deadlines, but not all of them. It really depends on where you live. Some states like Texas and Florida don't have income tax, so you wouldn't need to worry about state quarterly payments there. For states that do have income tax, you typically need to make quarterly payments if you expect to owe more than a certain amount for the year. The threshold varies by state - in California it's $500, in New York it's $300, etc. Your state's department of revenue website should have the specific requirements and forms.
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Kayla Morgan
4 Has anyone tried using TurboTax for quarterly payments? Their website says they can help calculate and pay quarterly taxes, but I'm not sure if it's worth the cost compared to just doing it directly through the IRS.
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Kayla Morgan
•11 I used TurboTax Self-Employed last year. It does calculate your quarterly payments pretty well and reminds you of deadlines, but you still have to actually make the payments through the IRS systems. So you're basically paying TurboTax for the calculation service and reminders. Honestly, I switched to just using a free spreadsheet template I found online and setting calendar reminders. I save the TurboTax fee and just pay directly through IRS Direct Pay now.
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