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A quick tip from someone who files extensions EVERY year - if you're really stuck, just pay MORE than you think you'll owe. The IRS is happy to return your overpayment when you finally file. I always add about 20% to my estimate as a buffer. Yes, you're giving the government an interest-free loan, but the peace of mind knowing you won't face penalties is worth it to me. I'd rather get money back than worry about underpaying.
But what if you really need that money in the meantime? Not everyone can afford to overpay by 20%. Wouldn't it be better to try to get it right?
That's a totally valid point. It really depends on your financial situation. If cash flow is tight, then absolutely try to be more precise with your estimate. Use your previous year's return as a guide and adjust for any major changes in income or deductions. For those who can swing it though, overpaying provides a stress-free extension. Another approach is to aim for that 90% threshold mentioned earlier - pay enough to cover 90% of your expected tax, which should protect you from the more significant penalties. Either way, the key is making a reasonable effort to estimate correctly based on the information you have at the time.
Don't forget that each STATE has different rules for extensions too! The federal extension doesn't automatically apply to state taxes. Check your state's requirements separately. I learned this the hard way last year when I got hit with state penalties even though I had a federal extension. Some states require their own extension forms, and some don't give extensions for payment at all, just for filing.
This is so important! I made this mistake with California taxes and ended up with penalties. Does anyone know a good resource that breaks down the requirements by state?
Don't stress OP, I didn't file my first tax return until I was 24! The good news is that if you've had taxes withheld from your paychecks (which you probably have), you're most likely owed money back. That's what a tax refund is. The easiest way to start is to use a free tax filing service like FreeTaxUSA or Cash App Taxes (used to be Credit Karma Tax). You literally just input the info from your W-2 forms and answer some basic questions. Grab those forms from your drawer and get started! For past years, you'll need to file separately for each year you missed. The tax software will have options for filing prior year returns.
Wait so I should use different software for the current year vs previous years? I'm trying to understand the process of catching up.
You can use the same software for all years, but you'll need to file each year separately. Most tax software has options for filing prior years. You'll just need to make sure you're using the correct forms for each tax year. When you start the process, you'll usually see an option like "File 2024 taxes" or "File for a previous year." You would need to go through the whole process once for each year (2022, 2023, 2024). Just make sure you have the W-2 forms for each corresponding year since the numbers will be different.
The normal deadline is April 15th each year for the previous year's taxes (so April 15, 2025 for your 2024 taxes). But if you're owed a refund, you actually have 3 years to file before you lose the money. So right now in 2025, you could still file for 2022, 2023, and 2024. If you owe money instead of getting a refund, then filing late can result in penalties. But since you're just starting out and probably don't make a ton of money, it's very likely you'll get refunds.
Former tax professional here. A few things to consider: 1. Make sure you create and keep copies of everything - your W2s showing withholdings, the audit letter, and any responses. 2. If you do what the auditor suggests, get it in writing from them (email is fine) that they acknowledge your withholdings will be applied after the case is closed. 3. You might qualify for penalty abatement under First Time Penalty Abatement if you haven't had other penalties in the past 3 years. This is separate from the audit and you'd request it after the audit is closed. 4. The strangest part of your situation is that the tax preparer should have included your withholdings on the original return. This makes me wonder if they made other serious errors too.
Thank you for this advice! The preparer definitely made multiple errors - that's why I got audited in the first place. I'll definitely ask for written confirmation about the withholdings. Do I need to wait until after the audit is completely closed to request the First Time Penalty Abatement, or can I mention it to the auditor now?
You should wait until the audit is fully closed before requesting First Time Penalty Abatement. Auditors typically don't handle penalty abatement requests during the audit process. Once everything is settled and you've paid the adjusted amount, then submit your penalty abatement request. If you've had a clean compliance history for the past 3 tax years (no penalties), you have an excellent chance of getting the penalties removed. Just be aware this only applies to certain penalties like failure-to-file and failure-to-pay, not all audit-related penalties.
Did you sign the audit agreement yet? If not, you should specifically ask the auditor to note in the file that you had $18,500 in withholdings that should be applied to the $23,000 liability. While it's true another department handles this, having it documented by the auditor creates a paper trail.
This is important advice. I've been through an audit where information "got lost" between departments. Always get everything in writing and create documentation trails.
If I could ask a CPA anything, I'd want to know about tax planning strategies that actually work for middle class people. Not the fancy stuff for millionaires, but practical ways regular people with W2 jobs and maybe a side gig can legally reduce their tax burden. Like, are FSAs and HSAs worth it? Should I be making traditional or Roth contributions? Is a 529 plan actually good or are there better ways to save for my kid's college? When is it worth itemizing vs taking the standard deduction?
This is such a good point. Most tax advice seems geared toward either really poor people qualifying for earned income credits or rich people with complex investments. What about us regular folks making between $60-120k? We need help too!
Exactly! The middle class gets squeezed the most it seems. We make too much to qualify for many credits but not enough to benefit from fancy tax strategies with investment properties and such. I think most people in our situation just don't know what options we have available. I'd love practical advice like "if you make X amount, here are the 3 most impactful things you can do to reduce your tax bill" with actual numbers and examples. Or even a checklist of things to consider based on your life situation (married, kids, homeowner, etc).
I'd ask a CPA about all these tax prep software options. Is TurboTax really worth the money? Are there better alternatives? And what things should I absolutely NOT try to DIY even with software help? I always worry I'm missing something major by doing my own taxes.
I switched from TurboTax to FreeTaxUSA last year and saved like $120 for basically the same service. But I'm always nervous about missing something too. Would love to know from an actual CPA what tax situations are too complex for software.
Liam O'Connor
Another option is to use the IRS Free File Fillable Forms. It's completely free no matter what credits you qualify for. The downside is that it's basically like filling out paper forms but on a computer - there's minimal guidance. But if you're fairly comfortable with taxes and just need to claim the Retirement Savings Credit, it might be worth looking into.
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Amara Adeyemi
ā¢Does the IRS Free File Fillable Forms have any income limits? I make around $85k and often get locked out of the "free" options.
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Liam O'Connor
ā¢The Free File Fillable Forms have no income limits at all - they're available to everyone regardless of income. That's different from the IRS Free File Program partners (like TurboTax Free File, etc.) which typically have a $73,000 income limit. The trade-off is that Fillable Forms provide no guidance or calculations - you're basically just filling in digital versions of the paper forms. You need to know which forms to complete and how to do the calculations yourself. Form 8880 for the Retirement Savings Credit isn't terribly complicated though, especially if you're just claiming for yourself and spouse.
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Giovanni Gallo
Just so you know, the Retirement Savings Contributions Credit phases out at higher income levels. If you're married filing jointly, it starts phasing out at $43,500 and completely disappears at $73,000 (for 2023 taxes). For singles, it phases out between $21,750-$36,500. Are you sure you actually qualify? If you're right on the edge, maybe double-check your AGI calculation. You might not actually qualify for the credit, which would solve the problem entirely.
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Fatima Al-Mazrouei
ā¢The 2023 income limits are actually a bit higher now: $73,000 for married filing jointly and $36,500 for singles (full phase-out points). But yes, checking if you're truly eligible is important!
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