1 Would I still qualify for an Offer in Compromise if I have decent income now? I'm making good money these days, but those back taxes are from when my business failed and I had almost no income for a while.

9 Current income is definitely a factor they consider, but it's not the only one. They look at your overall financial situation including assets, expenses, future earning potential, and ability to pay. Even with good current income, if the total debt is large enough compared to your projected ability to pay over the collection period, you might still qualify. The key is having a professional properly document your financial situation and submit the offer correctly. The forms and financial statements need to be accurate but presented in a way that shows why a settlement makes sense for both you and the IRS. The official term they use is "doubt as to collectibility" - they want to collect what's reasonable rather than an amount that would cause financial hardship.

13 They do allow back tax filing, but you have to buy the software for those specific years. You can still purchase previous year versions of TurboTax, but they're not always easy to find on their website. Search specifically for "TurboTax 2021" or "TurboTax 2022" and you'll find links to buy those versions.

Oh man I didn't even think about the Head of Household thing! That might explain the big difference when I ran the numbers last year. So if I understand right, whoever claims our son can probably file as Head of Household, and the other person has to file as Single? Does this mean we should really be looking at our COMBINED tax situation rather than individual returns? Like figuring out which combination of her filing status + my filing status + who claims our son = the best overall result for our household?

Yes, you've got it right! Whoever claims your son would likely qualify for Head of Household (assuming they meet the other requirements like paying for more than half the household expenses), while the other person would file as Single. Absolutely, you should be looking at your combined tax situation. It's not just about who gets the dependent deduction - it's about the whole package: different filing statuses, child tax credit, earned income credit if your incomes qualify, and other credits/deductions that phase out at different income levels. That's why running the numbers both ways like you did last year is the smart approach. The goal is to minimize your household's total tax burden, not just one person's taxes.

This is so true. When my partner and I were in this situation, we discovered a $3700 difference just based on who claimed our twins because of the earned income credit thresholds. It was actually better for the higher earner to claim them in our case, which seemed counterintuitive.

Thanks, that's really good to know. Do you remember what you included in that letter? I'm worried the penalties are going to be more than what I would have owed originally.

I explained the specific circumstances that prevented me from filing on time (in my case, a serious medical condition and related financial hardship). I included whatever documentation I could to support my claim - medical records, hospital bills, etc. For your situation, you might want to explain the timing of your incarceration and why it prevented you from filing. Be specific about dates and why you couldn't arrange for filing while incarcerated. The IRS looks for what they call "reasonable cause" - basically showing that you couldn't comply with tax obligations despite using "ordinary business care and prudence.

Also make sure you're using the right address to send it! Each state has different processing centers for paper returns. If you google "where to mail paper tax return 2018" plus your state name, you'll find the right address.

Does anyone know if changing jobs mid-year counts as reasonable cause? I switched employers in August and my withholding got all messed up even though I submitted a new W-4 right away.

A job change by itself typically doesn't qualify as reasonable cause for penalty abatement. The IRS expects you to adjust your withholding or make estimated payments to cover any shortfall. However, if there were unusual circumstances beyond your control with the new employer's payroll system, or if you requested proper withholding but they made errors, that could potentially qualify. The key is whether the situation was truly beyond your control despite taking reasonable steps to comply with tax requirements.

You only need to file Form 2210 if you didn't pay enough tax throughout the year via withholding or estimated payments. If your software didn't bring it up, you're probably fine! The form is specifically for calculating penalties for underpayment of estimated taxes. Most W-2 employees with proper withholding never see this form because their employers withhold taxes evenly throughout the year. It's more common for self-employed people, those with investment income, or people who had a change in income during the year.

OK boomer, but some of us actually need that money for bills and can't just wait around indefinitely while the government sits on it. Not everyone has the luxury of treating their refund like bonus money that can show up whenever.

I understand that many people depend on their refunds for important expenses. My point wasn't that delays don't matter - it's that they happen every year, and panicking doesn't help. If you absolutely need tax refund money by a certain date, the better long-term solution is to adjust your withholding so you're not giving the government an interest-free loan throughout the year. That way you have access to more of your money in each paycheck rather than waiting for a refund that's subject to processing delays every year.

I filed last Thursday electronically through TurboTax. My return was accepted by the IRS within an hour, and the Where's My Refund tool is already showing "approved" status. Seems like new submissions are still being processed normally.