19 This is really good advice! I work in a college financial aid office, and we do sometimes accept last paystubs as temporary documentation especially in cases like this. We'd still need the official documents eventually, but it can buy you some time with deadlines.

11 Thanks for the additional info! I didn't even think about the paystub option. You're right that the year-to-date information would essentially show the same income information that would be on the W-2. I should have also mentioned that the employer is required by law to provide a replacement W-2, so being persistent with them is important. If they refuse, you can actually report them to the IRS using Form 4852 (substitute for W-2), which also puts some pressure on them to comply.

16 Try the IRS Taxpayer Advocate Service instead at 877-777-4778. They specifically help with issues like this, especially when you have a hardship situation like a financial aid deadline. They're usually much easier to reach than the main IRS line.

Thank you so much for this! Quick question - for the mileage deduction, can I estimate based on delivery distances, or do I need exact records? I didn't keep a detailed log but I know approximately how many deliveries I made and the average distance.

For mileage, the IRS technically requires a contemporaneous log (meaning recorded at the time of the driving). But realistically, if you can create a reasonable reconstruction based on delivery records, app history, or even average distances with documentation of how many deliveries you made, that should be acceptable. For future reference, I recommend using a mileage tracking app like MileIQ or Stride that automatically logs your trips. For this year, create your best estimation based on whatever records you have - delivery totals, areas you typically delivered to, etc. Just be prepared to explain your methodology if ever questioned.

Yes! The IRS offers payment plans. If you owe less than $50,000, you can easily set up an online payment agreement at irs.gov. For amounts under $10,000, approval is usually automatic if you can pay within 3 years and have filed all required returns. There's a small setup fee (around $31 if you do it online with direct debit), and you'll still accrue some interest and penalties, but they're much lower than not paying at all. Just make sure you file your return on time even if you can't pay the full amount - the penalty for not filing is much worse than the penalty for not paying.

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.

Are there any downsides to filing an extension? Will it flag your return for audit or anything?

No, filing an extension is completely routine and doesn't increase your audit risk at all. Millions of people file extensions every year for all sorts of legitimate reasons. The only real downside is if you're expecting a refund, you'll have to wait longer to get it. And as I mentioned, if you owe money, you still need to estimate and pay by the April deadline to avoid penalties, even though you're filing the actual return later.

That's a great point about the last paystub! I actually found it in my email from July. It shows all the YTD totals which should be exactly what would be on the W2 since I didn't work there after that. This might be the easiest solution!