First-time independent contractor forgot to pay quarterly taxes - penalties?

What if they've missed two quarterly payments already? Would the first-time abatement still apply? Also, is there any form that needs to be filled out to request this abatement or do you just call the IRS?

The first-time abatement can still apply even if you've missed multiple quarterly payments within the same tax year - it treats the whole situation as one "first time" mistake. The key is having a good history for the previous 3 tax years. You don't need a special form to request abatement. You can call the IRS after filing your return, write a letter citing "first-time abatement request," or have your tax preparer request it when they're dealing with any penalty notices. Some tax software also has options to request abatement when you file.

Does this work for people who are full-time independent contractors too? I don't have any W-2 income at all, just 1099 work from multiple clients.

I'm skeptical about these online tools. How accurate is it with calculating the penalties? And does it actually help you fill out the forms or just give you numbers?

Yes, it absolutely works for full-time contractors! Actually, it's probably even more helpful in your case since you'd have more complex deduction situations with multiple clients. The system helps identify business expenses you might be missing too. For calculating penalties, it was spot-on in my case. It uses the same calculation formulas the IRS uses, including the current interest rates. And it doesn't just give you numbers - it walks you through completing Form 2210 (the underpayment form) and generating payment vouchers for each quarter. You can even download completed forms ready to submit.

Wait, how does this Claimyr thing actually work? I thought it was impossible to get through to the IRS. Do they have some special phone number or something?

Sounds like a scam tbh. The IRS doesn't give priority to certain callers. There's no magical way to skip the phone queue that millions of other taxpayers are stuck in.

It's not a special phone number or anything like that. Basically, they use technology that continually redials and navigates the IRS phone tree for you. When they finally get through to a real person, they call you and connect you directly to that agent who's already on the line. So you skip all the waiting and busy signals. It's definitely not a scam. They don't ask for any personal tax information - they're just getting you connected to the actual IRS. Then you speak directly with an IRS agent just like if you had called yourself and waited for hours. The difference is you don't have to sit there listening to hold music for half your day.

Oh man, I didn't even think about state taxes! Does anyone know if all states follow the same quarterly schedule as the federal government? And are the penalties calculated the same way?

Most states do follow the federal quarterly schedule (April 15, June 15, September 15, and January 15), but there are some exceptions. For example, some New England states have slightly different dates. The penalty calculations vary by state. Some states have harsher penalties than the feds, while others are more lenient. It really depends on where you live. Your best bet is to check your state's department of revenue website or call them directly - state tax agencies are usually easier to reach than the IRS!

Is that 15.3% on top of regular income tax? Geez, no wonder people say to set aside 25-30% of your contractor income.

Yes, that 15.3% is on top of your regular income tax! It's broken down as 12.4% for Social Security and 2.9% for Medicare. The thing that really caught me off guard is that when you're an employee, you only pay half of this (7.65%) and your employer pays the other half. But as an independent contractor, you're both the employee AND the employer, so you pay the full amount. That's why the general rule of thumb is to set aside 25-30% of your contractor income - it covers both income tax and self-employment tax.

This is really helpful, thank you! Quick question about the safe harbor rule - how do you actually prove that your total tax liability will be less than last year? Do you need to submit some kind of projection to the IRS, or is it something they figure out automatically when you file your return? I'm in a similar situation where I was W-2 for most of last year and only started contracting recently, so this might apply to me too.

The safe harbor rule is actually calculated automatically when you file your return - you don't need to submit any projections or special forms to the IRS ahead of time. Basically, if you pay at least 100% of what you owed in taxes last year (or 90% of what you'll owe this year, whichever is smaller), you're considered "safe" from underpayment penalties. Since you were W-2 for most of last year, your withholdings from that job likely already covered a big chunk of your prior year tax liability. When you file your return, the IRS compares what you paid during the year (through withholding + estimated payments) against these safe harbor thresholds. If you meet them, any underpayment penalties get waived automatically. The key is making sure you pay enough for the remaining quarters this year to hit that threshold. A tax pro or even tax software can help you calculate exactly how much you need to pay to qualify for safe harbor protection.