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One thing to consider with your basis carryforward situation is whether you have any other traditional IRA assets. The pro-rata rule could make this more complicated. If you have other pre-tax money in any Traditional, SEP or SIMPLE IRAs, you won't be able to just convert the non-deductible portion. You'll have to convert a proportional amount of pre-tax money too, which creates a tax liability. For example, if you have $5,000 in non-deductible contributions (your basis) and $45,000 in pre-tax traditional IRA money, any conversion will be 10% tax-free and 90% taxable because of the pro-rata rule. Many people overlook this when doing backdoor Roth conversions and end up with unexpected tax bills.
I fortunately don't have any other traditional IRA assets - I've always used my 401k for pre-tax retirement savings and only opened the traditional IRA temporarily for the backdoor process. So I think I'm ok on the pro-rata rule, but that's definitely an important point for others to consider. Actually, I'm wondering if there's any advantage to purposely waiting until the market goes up before doing the conversion next time? That way I could potentially use up some of this basis carryforward?
Intentionally waiting for the market to go up before converting could help use up your basis carryforward, but it comes with risks. The longer you wait to convert, the more potential tax liability you could create if investments grow substantially before conversion. Remember that any growth that occurs while the money sits in the traditional IRA will be taxable when you convert. So while waiting might help with the basis issue, it could create a different tax problem. Most financial advisors recommend doing the conversion quickly after contribution to minimize taxable growth. It's usually a better strategy to just continue with regular backdoor contributions and let the basis work itself out over time rather than trying to time the market for tax purposes.
Can someone explain how to calculate the amount that gets carried forward when doing the Form 8606? I'm about to do my first backdoor Roth and want to understand this better.
The basis carryforward calculation happens on Form 8606. If you contribute $6,000 (non-deductible) to a traditional IRA but the value drops to $5,500 before you convert to Roth, you'll have: - Line 5: $6,000 (your non-deductible contribution) - Line 8: $5,500 (the amount you actually converted) - Line 9: $0 (assuming no previous basis) - Line 10: $6,000 (from line 5) - Line 11: 1.000 (divide line 10 by line 8, but capped at 1.000) - Line 13: $5,500 (line 8 × line 11) - Line 14: $500 (line 10 minus line 13) That $500 on line 14 is your basis carryforward to next year's Form 8606.
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My tax guy always says that even a short-term property sale won't trigger self-employment tax unless you've been making substantive improvements with the intention to sell for profit. Living in it as your primary residence indicates personal use, not a business activity. Your brother should keep good records though - document that he's living there as his primary residence, keep all utility bills, change his address officially, register to vote there, etc. The more evidence he has that this was his home (not an investment property), the better position he'll be in if questions ever come up. I think your brother's plan makes sense given the rent increase. Even with potential capital gains tax, he might still come out ahead compared to paying the higher rent for three years.
Does he need to do anything special on his tax forms to show it was his primary residence even though he didn't meet the 2-year test? Is there a specific form or something?
There's no special form specifically for declaring a primary residence that doesn't meet the 2-year test. He would report the sale on Schedule D and Form 8949 like any capital gain, but the key is keeping those supporting documents we discussed in case of questions. If he qualifies for a partial exclusion due to work-related move, health reasons, or unforeseen circumstances, he would need to fill out Form 2119. But from what you've described, planned retirement and moving overseas probably wouldn't qualify as an unforeseen circumstance, so he should plan on paying the full capital gains tax.
My parents just went through this! They bought a house, then dad got transferred unexpectedly and they had to sell after only 14 months. The tax part was actually pretty straightforward - they just paid capital gains tax on the profit (thankfully housing prices hadn't gone crazy in their area so it wasn't much). One thing they learned - if you have a legit reason for selling before 2 years, like job transfer, health issues, or certain other "unforeseen circumstances," you might qualify for a partial exclusion of capital gains. Doubt retirement plans would count though since that's a known, planned event.
Did they use TurboTax or some other tax software to figure all this out? I'm trying to decide if I need an accountant for my situation or if the tax software can handle these kinds of scenarios.
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You should file Form 8919 "Uncollected Social Security and Medicare Tax on Wages" with your return if your employer didn't properly withhold. This lets you report the income without paying self-employment tax on it. Also check with your state tax department - some states have protections for employees when employers mess up withholding.
But they did withhold Social Security and Medicare - just not federal income tax. Does Form 8919 still apply in my situation?
You're right - Form 8919 wouldn't apply in your situation since your employer did properly withhold Social Security and Medicare taxes. I misunderstood your original post. For federal income tax withholding issues, there unfortunately isn't an equivalent form. Since you correctly filled out your W-4, this is definitely the employer's mistake, but as others have mentioned, the IRS still considers the tax liability yours. Your best options are still to speak with management about potential compensation and set up a payment plan with the IRS for any amount you can't pay immediately.
Have you looked into filing for abatement of penalties? While you'll still owe the tax amount, you might qualify for first-time penalty abatement if you haven't had any issues in the past 3 years. That could at least reduce the amount by removing penalties. Worth asking the IRS about when you call them.
This! I had a similar situation and got the penalties removed. You still have to pay the base tax but it saved me a few hundred in penalties. The IRS form to request this is pretty straightforward.
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22 Don't overlook state taxes in all of this! I made that mistake when catching up on my back taxes. Got all my federal returns sorted out and then realized I still had to deal with state returns. Each state has different requirements and look-back periods.
1 Oh geez I hadn't even thought about state taxes! Do you know if Missouri has the same 6-year lookback period as the IRS? Or do I need to file all 10 years with the state?
22 Missouri generally follows the federal statute of limitations, so the 6-year lookback period is similar. However, there are some important differences. Missouri's Department of Revenue can be a bit more aggressive about collecting on older debts than the IRS in some cases. The good news is that Missouri offers voluntary disclosure programs that might help reduce penalties if you come forward voluntarily before they contact you. I'd recommend checking the Missouri DOR website or calling them directly after you get your federal situation straightened out. In my experience, state tax agencies are actually easier to reach by phone than the IRS.
5 Just wondering, has anyone used those tax relief companies that advertise on the radio? They claim they can settle your tax debt for pennies on the dollar. Are those legit or just scams?
8 Most of those "pennies on the dollar" tax relief companies are extremely misleading. What they're referring to is the IRS Offer in Compromise program, which is legitimate but has very strict qualification requirements that most people don't meet. These companies often charge thousands upfront with no guarantee of results. The reality is that if you have assets or a decent income, you likely won't qualify for significant reductions. The IRS has standard formulas they use to determine eligibility. You're better off working directly with the IRS or hiring a reputable local tax professional who charges reasonable fees. The IRS provides payment plans that most people can qualify for without needing a special "tax relief" company.
DeShawn Washington
Hey, just wanted to add some practical advice as someone who's worked cash jobs through high school and college. Keep a simple notebook or use a notes app on your phone and write down EVERY payment - date, amount, and what it was for. Take a picture of the cash before you deposit it too. When you deposit cash, don't do it all at once. Small regular deposits that match the work you're doing won't raise flags. And remember, banks are required to report cash deposits over $10,000, but they also report patterns of deposits just under that amount (called "structuring" which is actually illegal).
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Mei-Ling Chen
•Is there a specific app you'd recommend for tracking cash payments? And do you actually need to take pictures of the physical cash? What does that prove exactly?
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DeShawn Washington
•I just used the regular notes app on my phone, nothing fancy. The key is consistency - record everything right when you get paid so you don't forget. Taking pictures of cash isn't absolutely necessary for tax purposes, but I found it helpful when I needed to look back and verify amounts. It's more a personal record-keeping tip than a legal requirement. The most important thing is documenting when and how much you earned so you can accurately report it at tax time.
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Sofía Rodríguez
Just so you know, your parents might still need to be involved here. Since you're 15, they'll still claim you as a dependent on their taxes. If you make enough from your jobs (both regular and cash), you might need to file your own return, but your status as a dependent doesn't change. Also, most banks require an adult co-signer for minors under 18 anyway, so your parents probably have access to see your deposits. Better to be upfront with them now than have them surprised later!
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Aiden O'Connor
•That's actually not completely true. The rules for dependents filing their own returns depend on both earned and unearned income. For 2025, if your earned income is over $12,950, you need to file your own return even if someone claims you as dependent.
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Sofía Rodríguez
•Thanks for the clarification. You're right about the filing threshold for earned income. The important thing for the original poster to understand is that being a dependent doesn't mean your parents file for your income on their return - you'd still need to file your own if you meet the thresholds. The point about bank accounts is still relevant though - as a minor, the parents will have visibility into banking activity in most cases, so having a conversation about the cash income is important.
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