Thank you for this detailed response. We've checked the letter more carefully and it does have a CP504 notice number on it, so I think it's legitimate. What's the difference between Currently Not Collectible status and an Offer in Compromise? Would either of these permanently resolve the debt or just delay collection?

Currently Not Collectible (CNC) status temporarily pauses collection actions when paying the tax debt would create an economic hardship. The debt doesn't go away, but the IRS stops trying to collect while you're in financial hardship. The IRS reviews your status periodically (usually annually) to see if your financial situation has improved. An Offer in Compromise (OIC) is a settlement agreement where the IRS accepts less than the full amount owed to resolve the debt permanently. You have to demonstrate that you cannot pay the full amount due to financial hardship, and they consider your income, expenses, asset equity, and ability to pay. If accepted, you fulfill the terms of the offer (usually a reduced lump sum or payment plan), and the debt is considered paid in full.

Innocent Spouse Relief only applies if the debt is from a joint tax return where one spouse didn't know about income that wasn't reported or incorrect deductions. From OP's post, it sounds like this is solely the wife's tax debt, not joint debt, so probably wouldn't apply here.

Thanks for clarifying! You're right - I missed that detail that it's solely in her name. In that case, exploring the hardship provisions others mentioned is probably the better route.

How complicated was it to switch from partnership to S-Corp taxation? Did you have to create a new entity or just file some paperwork? Also, ballpark, how much did you save in taxes by making the switch?

The switch wasn't that complicated - just filed Form 8832 to be taxed as a corporation and then Form 2553 for the S-Corp election. Didn't need to create a new entity at all. The LLC remained the same, just the tax treatment changed. As for savings, it varies based on profit levels, but we probably saved around $15,000-$20,000 in self-employment taxes the first year after switching. The key is paying ourselves reasonable salaries (which are subject to FICA taxes) and taking the rest as distributions (which aren't). Just make sure you have a good accountant to help determine what's "reasonable" for your industry and area.

Nevada is way better for LLCs if you can establish a presence there. No state income tax and way lower fees. That's what my cousin did with his construction business after getting killed with California fees for years.

That sounds really promising. Do you find the monthly bookkeeping actually helps with your business throughout the year or is it mainly just for tax prep?

It's been incredibly helpful throughout the year. I get monthly profit and loss statements that help me track where money is going, which has helped me identify areas to cut costs. The bookkeeper also helps me understand which parts of my business are most profitable. Tax time is so much easier now too. Instead of scrambling to organize a year's worth of receipts and transactions, everything is already categorized and ready. My CPA literally told me I'm saving money on tax prep because they don't have to spend hours organizing my financial information first.

I tried that route one year and ended up missing a major deduction that an accountant caught the following year. Software is fine for W-2 employees but business taxes have too many gray areas where professional judgment matters.

What exactly happens if you miss the deadline completely? Does the IRS automatically find out and penalize you, or is it something that only comes up if you get audited? Asking for a friend who may have missed this deadline last year...

If the excess contributions aren't removed by the deadline, they unfortunately remain in the plan and yes, they can be double-taxed. The excess amount will still be included in your taxable income for the year you made the contribution, and then it will be taxed again when you eventually withdraw it in retirement. There's no immediate penalty per se, but the double taxation is the real cost. The IRS doesn't automatically flag this - it would typically only come up during an audit. However, many plan administrators now report contribution limits to the IRS, so it's becoming more likely to be caught. Your friend should consult with a tax professional about their specific situation as there might be some remediation options depending on their circumstances.

This is actually incorrect advice that could cause more problems. You can't simply "redesignate" excess 401k contributions as after-tax contributions. The 401k contribution limit applies to the total of traditional and Roth contributions combined. After-tax contributions (non-Roth) are different and subject to the overall annual addition limit, not the employee deferral limit. What you might be thinking of is excess IRA contributions, which can sometimes be recharacterized, but 401k excess deferrals must be distributed with earnings.

You're right and I misspoke. I was confusing 401k with IRA recharacterization options. For 401ks, distribution of the excess is generally the only option. Thanks for the correction! What I should have mentioned is that some 401k plans do have after-tax contribution options (separate from Roth) which have different limits, but that wouldn't help with excess contributions to the regular pre-tax/Roth portion that's subject to the $23,000 limit for 2025.

What if I already filed my taxes but didn't include these losses? Can I file an amended return to claim them or would that increase my audit risk?

You can absolutely file an amended return to claim losses you forgot to include. Use Form 1040-X for the amendment along with a corrected Schedule D showing the capital losses. The general time limit for filing amendments to claim a refund is within 3 years from the date you filed your original return or within 2 years from when you paid the tax, whichever is later. As for audit risk, claiming legitimate losses you're entitled to shouldn't significantly increase your risk if you have the documentation to support them. Just make sure you keep records showing your basis in the shares and evidence of when they became worthless.

In TurboTax, you need to go to the Investments & Rental Properties section, then select Stocks, Mutual Funds, Bonds, Other. It will ask for the sale information and your cost basis. Make sure to enter your actual sales (even if pennies) rather than just marking it as worthless. It does track carryforward losses automatically for future years.