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One extra tip: if you're filing multiple back years, don't use the standard Free File options. They usually only support the current and maybe previous year. I had to file 3 years back and ended up using FreeTaxUSA which supports filing returns back several years for a reasonable fee. TurboTax wanted a fortune for each past year. Also, set up an IRS online account NOW, before you need it. It takes a couple of weeks sometimes to verify your identity, and you'll want access to view your transcripts and track your refunds.
That's super helpful, thanks! Is it difficult to set up the IRS online account? I've heard horror stories about identity verification issues.
The IRS account setup is hit or miss. Make sure you have your phone in hand (they text a verification code) and a credit card or loan account number for additional verification. Most people get through fine, but about 30% of users hit snags with identity verification. If online verification fails, you'll need to either schedule a video interview or visit a local IRS office in person. The video option is much faster - usually within a week versus potentially months for an in-person appointment.
Has anyone been audited after filing multiple years of back taxes? I'm in a similar boat (4 unfiled years) and paranoid that suddenly filing everything will trigger an audit.
I filed 3 years at once back in 2023 and didn't get audited. But I made sure everything was accurate and had documentation for all my deductions just in case. From what I understand, simply filing back taxes doesn't automatically trigger an audit - it's more about what's IN those returns (unusual deductions, major discrepancies, etc).
Does anyone know if the court ruling affects the penalties for non-compliance? I heard the penalties were supposed to be pretty severe - like $500/day and potential criminal charges for willful violations. If the courts eventually uphold the CTA, could they still enforce penalties for the time period when we thought we didn't have to file?
As I understand it, if the injunction is eventually overturned and the BOI requirements are upheld, FinCEN would likely establish new compliance deadlines rather than trying to enforce the original ones retroactively. It would be pretty unreasonable to penalize businesses for non-compliance during a period when a court order explicitly stated they didn't have to comply. The penalties are indeed significant - civil penalties of $500 per day for violations, plus potential criminal penalties including imprisonment for willful violations. But these would only apply to violations of whatever new deadlines might be established if the CTA is ultimately upheld.
That makes sense, thanks for the clarification! I was worried we might get caught in some kind of legal trap if we don't file now but then the requirements come back later. I'll just keep our information ready but hold off on filing until there's more clarity.
My accountant told me to just go ahead and file the BOI reports anyway despite the injunction, saying "better safe than sorry." Does that make any sense to anyone? FinCEN is still accepting filings through their website, but I'm not sure if there's any benefit to filing when it's not currently required.
I think your accountant is being overly cautious. While FinCEN's system remains operational and you technically *can* still file, there's no legal requirement to do so while the injunction is in effect. There's no penalty for not filing right now. Unless you have some very specific business reason for wanting your beneficial ownership information on file with the government during this period of uncertainty, I'd recommend waiting to see how the legal situation resolves. Just keep your information organized so you're ready if/when the requirement comes back.
I think people are overlooking a critical detail in your question. You said you were on your parents' insurance "last year" but then got your own insurance in January 2024. So you were on their plan for all of 2023? If that's true, then you simply cannot make contributions to your own HSA for 2023. The "last month rule" that someone mentioned only applies if you had your own HSA-eligible health plan by December 1st, 2023. Your parents' unused contribution space ($1450) remains with their HSA - it doesn't transfer to you. Your contribution limit for 2024 will be based on your new individual coverage starting in January 2024.
But what if their parents added them as an authorized user on their HSA? Couldn't they contribute that way since it's still part of the family limit?
Being an authorized user on someone else's HSA is different from having your own HSA eligibility. Authorized users can withdraw funds from someone else's HSA for qualified medical expenses, but they don't gain contribution rights. HSA contribution eligibility is tied to having your own HDHP coverage. Being covered as a dependent on someone else's family plan doesn't make you eligible to contribute to any HSA, either yours or theirs. The family contribution limit belongs to the HSA account owner (the parents in this case), not to the dependents covered under their plan.
Has anyone considered whether the "testing period" for HSA might apply here? If you maintain HSA-eligible coverage through December 31, 2024, couldn't you use the last-month rule to make a full 2023 contribution?
You've got the testing period concept right but the year wrong. The "last-month rule" would only help for 2023 contributions if OP had their own HSA-eligible coverage by December 1, 2023 (which they didn't). Since they only got their own HDHP coverage in January 2024, the last-month rule might apply to their 2024 contributions (if they maintain coverage through Dec 31, 2024), but it can't retroactively create eligibility for 2023.
Something nobody's mentioned yet: if you're really desperate for tax deductions but don't want to get a mortgage, consider increasing your charitable giving. It's a much better financial move than paying interest to a bank! You get to support causes you care about AND get a tax deduction. Plus you're not enriching a financial institution. Just make sure you donate enough (along with other potential itemized deductions) to exceed the standard deduction amount.
That's actually a really thoughtful suggestion. We do give to our church and a couple local charities already, but hadn't thought about the tax angle. Would bunching donations in alternating years work better to get over the standard deduction threshold?
Yes, bunching donations is exactly what many financial planners recommend! For example, if you normally donate $5,000 per year, you could instead donate $10,000 every other year. This might push you over the standard deduction threshold in donation years (when you itemize) while taking the standard deduction in off years. Another option is a Donor Advised Fund, where you contribute a larger amount in one year for the tax deduction, but distribute the actual donations to charities over multiple years. This gives you the tax benefit immediately while allowing you to support charities gradually.
My accountant actually laughed when I asked this same question last year lol. She said getting a mortgage for the tax deduction is like buying something you don't need just because it's on sale - you're still spending money unnecessarily! She also pointed out that with the higher standard deduction now ($27,700 for married filing jointly in 2023), many people don't even benefit from the mortgage interest deduction unless they have a really big mortgage or tons of other itemized deductions. You'd need more than $27,700 in itemized deductions for it to even matter.
Dmitry Petrov
One thing nobody's mentioned yet - check if you're still within the timeframe for a "corrective distribution" for your 2022 overcontribution. If you took the distribution before your filing deadline (including extensions) for 2022, you can avoid the 6% excise tax completely, even if Vanguard coded it incorrectly on the 1099-R. For the earnings portion, you generally need to include those as income in the year you made the contribution (2022), not when you took the distribution (2023). If your 1099-R doesn't separately show the earnings, you might need to contact Vanguard to get that breakdown. The most critical form here is Form 5329 where you'll need to show you corrected the excess contribution. Even with an incorrect distribution code, you can still properly document this with an attached statement explaining the situation.
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Mei Wong
β’Thanks for this info! I did take the distribution in February 2023, which was before my filing deadline for 2022 taxes. But I'm confused about reporting the earnings - my 1099R doesn't break out what portion was earnings vs. principal. Does this mean I need to amend my 2022 return now to report those earnings? Or can I handle everything on my 2023 return?
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Dmitry Petrov
β’Since you took the distribution before your 2022 filing deadline, you should definitely avoid the 6% excise tax, which is good news. For the earnings portion, yes, technically those earnings should be reported on your 2022 tax return, which would mean filing an amendment if you've already filed for 2022. You'll need to contact Vanguard to get the breakdown of principal vs. earnings from that distribution. Ask specifically for the "net income attributable" or NIA related to the excess contribution amount. This might not be reflected correctly on your 1099-R if the distribution wasn't properly coded.
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Ava Williams
Heads up - I went through this exact same mess with Fidelity last year. Make sure you also check if you qualify for the "self-certification" procedure under Revenue Procedure 2021-30. If your correction doesn't fully meet all the technical requirements for a proper return of excess contribution, you might still qualify for relief under this procedure. It essentially lets you "self-certify" that you intended to follow the rules for proper correction even if there were some procedural errors along the way. You'll need to file a specific statement with your return, but it could help avoid penalties even if Vanguard didn't process everything perfectly.
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Miguel Castro
β’I've never heard of this self-certification procedure. Does it apply to 401k contribution corrections too or just IRAs? I overcontributed to both last year and am trying to sort through the mess.
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