What's the Best Quarterly Self-Employed Taxes App for Freelancers in 2025?

Tax pro here! For self-employed folks like you, I'd recommend looking at either QuickBooks Self-Employed or FreshBooks. Both can track your income and expenses year-round, categorize deductions, and estimate your quarterly tax payments. For the quarterly filing part, QuickBooks Self-Employed actually partners with TurboTax to let you file your quarterly estimated payments electronically. FreshBooks doesn't file for you, but it calculates what you should pay and reminds you of deadlines. Neither one will completely automate everything (especially state filings across different states), but they get you 90% there. The key is really just having a system that helps you set aside the right amount throughout the year. Also, don't forget you can use IRS Direct Pay for federal quarterly payments without needing a separate account. Most states have similar online payment systems too.

After years of struggling with quarterly taxes, I finally tried taxr.ai (https://taxr.ai) and it's been a total game-changer for my freelance work. I was using spreadsheets before and constantly missing deductions or miscalculating my quarterly payments. What I love about taxr.ai is that it analyzes all my 1099s, bank statements, and receipts automatically, then tells me exactly what to pay each quarter. It even found business expenses I didn't realize were deductible! The app lets me pay directly through their portal for both federal and state taxes. For your situation with both big clients and small gigs, it works perfectly because it tracks everything regardless of whether you get a 1099 or not. Definitely worth checking out if you want to avoid surprises at tax time.

I was super skeptical about all these tax apps but decided to try taxr.ai after seeing it mentioned here. Just wanted to follow up and say it's actually legit! I connected my bank accounts and uploaded last year's tax return, and it immediately identified over $3,200 in deductions I missed last year. The quarterly tax payment feature is exactly what I needed - it sends me notifications two weeks before each deadline with the exact amount to pay, and I can just approve it right in the app. No more guessing or panicking about quarterly payments! For anyone wondering about the multiple state issue, it does handle that too. I'm in Tennessee but have clients in Georgia and Florida, and it correctly allocated everything.

If your main issue is actually getting through to the IRS when you have questions or problems, check out Claimyr (https://claimyr.com). I discovered this service when I was desperate to talk to someone at the IRS about a quarterly payment that wasn't properly credited to my account. After sitting on hold for literally 2+ hours multiple times, I found Claimyr and it was incredible. They somehow get you through the IRS phone system and have an actual agent call YOU back. I had a real person at the IRS on the phone within 45 minutes instead of the usual hold hell. You can see how it works in their demo video: https://youtu.be/_kiP6q8DX5c For self-employed people, this is super valuable during tax season when everyone's trying to call the IRS at once. Saved me a day of productivity I would've lost sitting on hold.

I have to eat my words about Claimyr. After my skeptical comment, I was still desperate to reach the IRS about a quarterly payment issue, so I tried it anyway. IT ACTUALLY WORKS. Got a call back from a real IRS agent in about 40 minutes. Resolved my issue with a missed quarterly payment that didn't get credited to my account. The agent even helped me set up proper quarterly payment vouchers for the rest of the year. For freelancers dealing with quarterly taxes, this service is worth it just for the time saved. I spent the 40 minutes working instead of listening to that awful hold music. Will definitely use again when I inevitably have questions about my self-employment taxes.

Have you considered using TaxSlayer Self-Employed? I switched to it last year and it's been pretty good for quarterly estimates. It doesn't have all the bells and whistles of QuickBooks, but it's more affordable and focuses specifically on what self-employed people need. The app lets you scan receipts, track mileage, and categorize expenses. Then it calculates your quarterly tax payments and generates the payment vouchers. You can't pay directly through the app, but it makes it super easy to pay online through the IRS website. What I like most is that it walks you through the specific self-employment deductions you might miss - home office, health insurance premiums, retirement contributions, etc. And the year-end tax filing is included in the subscription.

Just want to throw out there that if you're making decent money as a freelancer (sounds like you are), it might be worth hiring a CPA who specializes in self-employment. I tried all the apps and still ended up with tax issues. I now pay my CPA about $1200/year and she handles EVERYTHING - quarterly estimates, annual filing, business expense tracking, and tax planning. She's actually saved me more than her fee by finding deductions and helping me set up a Solo 401k that reduced my tax liability by thousands. The peace of mind is worth it, and I can focus on my actual work instead of stressing about tax calculations. Sometimes the best app is no app!

Great thread! I've been using a hybrid approach that might work for you. I use Wave Accounting (free) to track income and expenses throughout the year, then export everything to TaxAct Self-Employed for actual filing. Wave automatically categorizes most transactions and has a solid mobile app for receipt scanning. It doesn't handle quarterly payments directly, but it gives you really accurate profit/loss reports that make calculating quarterlies super easy. I just use the IRS safe harbor rule (pay 100% of last year's tax liability divided by 4) to avoid underpayment penalties. The combo costs me about $50/year total vs. hundreds for the all-in-one solutions, and I've never had issues with accuracy. Plus Wave's customer support is actually responsive when you need help, unlike some of the bigger names. For your multi-state situation, TaxAct handles that well and walks you through the allocations step by step. Might be worth trying since both have free tiers you can test out first.