If you're a 1099 worker figuring out quarterly estimated taxes for the first time, here's the short version: you owe four payments in 2026 (April 15, June 15, September 15, and January 15, 2027), the IRS wants the smaller of 90% of what you'll owe this year or 100% of what you owed last year (110% if your prior-year AGI was over $150,000), and only one of the four tools most freelancers reach for actually moves the money aside for you instead of just telling you the number.
Why this catches so many freelancers off guard
Nobody withholds anything from a 1099 payment. When you worked a W-2 job, your employer sent a slice of every paycheck to the IRS automatically and you never thought about it. As a gig worker, that slice is now your job to calculate, set aside, and mail in four times a year, and the IRS charges you a penalty (calculated as interest, currently tied to the federal short-term rate plus 3%) if you fall short. Most people find this out the hard way in April, when a $4,000 tax bill shows up with no cash set aside to cover it.
The 2026 quarterly deadlines
- Q1 2026 income: due April 15, 2026
- Q2 2026 income: due June 15, 2026
- Q3 2026 income: due September 15, 2026
- Q4 2026 income: due January 15, 2027
You're required to make these payments if you expect to owe $1,000 or more for the year after subtracting withholding and credits (source: irs.gov, Estimated Taxes, checked August 2026). For most gig workers with no W-2 withholding at all, that threshold is trivial to cross.
How much to actually set aside
The self-employment tax rate is 15.3% on your net self-employment earnings: 12.4% for Social Security (on the first $184,500 of income in 2026, up from $176,100 in 2025) and 2.9% for Medicare, with an additional 0.9% Medicare surtax above $200,000 for single filers (source: rudler.cpa, 2026 Social Security wage base, checked August 2026). That's before federal income tax on top, which for most solo freelancers lands somewhere in the 12% to 24% bracket depending on total income. Add it up and the standard rule of thumb, setting aside 25% to 30% of net income, holds up for most people, though it's worth running your own numbers if you're near a bracket edge or you live in a state with income tax.
The safe harbor rule that keeps you out of penalty territory
You avoid the underpayment penalty entirely if your total withholding and estimated payments for the year equal the smaller of two numbers: 90% of what you'll actually owe for 2026, or 100% of what you owed for 2025. If your 2025 adjusted gross income was over $150,000 ($75,000 if you're married filing separately), that second number becomes 110% instead of 100% (source: irs.gov, Estimated Taxes, and keepertax.com, Safe Harbor Rule, both checked August 2026). In practice, the 100%/110% prior-year option is the one most freelancers use, because it only requires last year's tax return, not an accurate forecast of a year that hasn't finished yet.
Which tool actually calculates it for you
All four of these track income and expenses well enough to estimate a quarterly number. What actually differs is whether that number requires a paid tier to unlock, and whether the tool stops at telling you the number or goes further and moves the cash.
| Tool | Annual cost | Quarterly estimate included? | Auto-sets money aside? |
|---|---|---|---|
| FlyFin (Basic) | ~$84/yr | Yes, on every tier | No, calculator only |
| Keeper | $199/yr (Standard) / $399/yr (Premium) | Estimate on Standard; quarterly payment support only on Premium | No |
| Bonsai Tax | Folded into Bonsai suite, from $9/mo | Yes, estimates from tracked income and expenses | No |
| Lili (Pro) | $180/yr ($15/mo) | Indirectly, via automatic allocation | Yes, automatically allocates funds toward tax payments |
FlyFin's quarterly calculator ships on its cheapest plan (source: freelancerprofit.com, FlyFin review, checked August 2026), so if all you want is the number, it's the least you'll pay for it. Keeper puts the actual estimate on its $199 Standard plan but reserves "quarterly tax payment support" for the $399 Premium tier (source: keepertax.com/pricing, checked August 2026). Bonsai Tax doesn't sell as a standalone product at a separate price. It's a feature inside the main Bonsai suite, which starts at $9/month for the Basic plan (source: hellobonsai.com/pricing and hellobonsai.com/taxes, checked August 2026). Lili is the outlier: instead of just estimating what you'll owe, its Pro plan and above will automatically move a percentage of incoming deposits into a separate tax sub-account, so the money isn't sitting in your checking account tempting you to spend it (source: lili.co/plans, checked August 2026). That's not available on Lili's free Core tier.
Which one to actually use
If you already bank with Lili or are willing to switch, its Pro plan is the only one of these four that solves the actual problem, which isn't knowing the number, it's having the cash on hand when the deadline hits. If you're not moving your banking, pair a cheap calculator (FlyFin's Basic tier) with a standing transfer of 25% to 30% of every payment into a separate savings account the day it lands. That combination costs less than Keeper Premium and does the same job in two steps instead of one.
FAQ
Do I owe a penalty if I miss one quarterly payment but catch up by April? Yes. The IRS calculates the underpayment penalty per quarter, not on your year-end total, so paying it all in April still leaves you owing interest on the quarters you missed.
What if my income is irregular and I can't predict what I'll owe? Use the 100%/110% prior-year safe harbor instead of trying to forecast the current year. It only requires knowing last year's tax bill, which is fixed, not this year's, which isn't.
Can I just pay one big estimated payment instead of four? No. The IRS still assesses the penalty by quarter, so paying the full year's estimate in April doesn't cover the underpayment on the earlier quarters that hadn't been paid yet.
Do I need a separate bank account for taxes? Not strictly, but every solo operator I've talked to who stopped missing payments did it by moving the money out of their spending account the same day it arrived, whether that's a manual transfer or Lili's automatic allocation.
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