Your accountant is partly right, but timing is crucial. Recharacterization was an option before the tax filing deadline (including extensions) for the year of the contribution. For 2019 contributions, that deadline would have been around July-October 2020 (extended due to COVID). Since we're in 2025 now, recharacterization is no longer an option for 2019 contributions. The OP will need to go with the Form 5329 and penalty approach. But your suggestion is definitely good advice for anyone who catches their over-contribution more quickly!

That's a really good point I hadn't considered. I haven't calculated the exact earnings on the excess portion, but given market performance since 2019, it's probably significant. If I'm using the "absorption" method by under-contributing in 2021, do I still need to worry about the earnings issue? Or does that only apply if I'm physically removing the excess contribution?

If you're using the "absorption" method by under-contributing in a later year, you don't need to worry about withdrawing the earnings. The earnings stay in your Roth IRA and continue growing tax-free, which is actually a nice benefit! The earnings only become an issue if you physically withdraw the excess contribution. In that case, you'd need to calculate and withdraw the proportional earnings as well. Since you've already effectively "fixed" the excess through your 2021 under-contribution, you just need to file Form 5329 for 2019 and 2020 to pay the penalty for those years. The earnings can stay put in your account.

That's helpful to know! I'm using TurboTax and wasn't sure how to handle this. So when TurboTax asks for the amount in Box 12W, I should enter the full $6,000 that's shown, but then somewhere else I'd indicate my actual HSA contributions were only $4,350?

Yes, exactly. Enter the full $6,000 when TurboTax asks for the Box 12W amount - you want to accurately report what's on your W2. Then, when TurboTax walks you through the HSA contribution section, you'll have the opportunity to enter your actual HSA contributions of $4,350. TurboTax will properly complete Form 8889 with all this information. The software is designed to handle these kinds of discrepancies. You may also want to add a brief explanation in the notes section mentioning that Box 12W incorrectly includes healthcare premiums. Most people never have their returns manually reviewed, but if yours is, this note could be helpful.

This is reassuring! Do you think it's worth pushing the employer to correct the W2, or is it easier to just file Form 8889 correctly and not worry about it?

I thought Solo 401ks were only for self-employed individuals without employees. Doesn't an S-Corp usually have at least the owner as an employee? Would this still work if the owner is the only employee?

You're right to question this - I should have been more specific. A Solo 401k can work for an S-Corp if the only employees are the owner (and potentially their spouse). If the S-Corp has any other W-2 employees who work more than 1,000 hours per year, then you'd need a regular 401k plan with non-discrimination testing. If OP only has themselves (and possibly their spouse) as employees, then the Solo 401k is still an option and could allow for higher contribution limits than a SEP IRA in many cases, especially when you consider both the employer and employee contribution components.

Not a dumb question at all, but with an S-Corp, the home office deduction works differently than for sole proprietors. The corporation should reimburse you for the home office expenses rather than taking them directly on your personal return. The S-Corp can deduct the reimbursement and it's not taxable income to you if done correctly.

I had no idea about this rule! So if I stay on my HDHP through all of 2024, I can keep the full $3850 contribution for 2023, even though I only had coverage starting in May 2023? Do I need to indicate this somehow on my 2023 Form 8889?

Yes, exactly! If you had HDHP coverage on December 1, 2023, you qualify for the "last-month rule" and can contribute the full $3,850 for 2023 - as long as you maintain HDHP coverage for all of 2024. On Form 8889, you'll need to check the box on line 3 that says "If you, and your spouse if filing jointly, had an HDHP for the entire year, check the box..." This indicates you're using the last-month rule. You would then enter the full-year contribution limit on line 3. Just remember this comes with that testing period requirement - if you don't maintain HDHP coverage through December 31, 2024, you'll have to include the "excess" portion in your income for 2024 plus pay that additional 10% tax.

Yes, you absolutely need to file Form 8889, even with employer payroll deductions. Your tax software might not be prompting you because it doesn't know you have an HSA. You need to specifically tell it that you contributed to an HSA. Look for the section in your tax software about HSAs, health accounts, or tax deductions/credits. Once you indicate you have an HSA, it should generate Form 8889. The form is required for ALL HSA contributions and distributions, regardless of how they were made. Your W-2 should show HSA contributions in box 12 with code W if they were made through payroll.

Thank you for this insight - that's really helpful to know about them looking at earning potential. I have a question though - my earning history has been inconsistent because of contract work, with some years much higher than others. Will they just look at my highest earning year and assume that's my potential? Or do they take into account the volatile nature of contract work?

They typically look at an average of your recent years, but they'll definitely take into account your highest earning years as an indication of what you're capable of earning. However, if you can document that the contract work was irregular or that the industry has changed (especially with the company going bankrupt), that can help your case. Make sure to thoroughly document why your past income isn't representative of future earnings. Include any industry changes, health issues, or other factors that limit your earning potential going forward. The more documentation you provide showing why your situation has permanently changed, the better your chances of having them accept a reduced earning potential calculation.

Did you use a tax professional or do it yourself? I've been watching YouTube videos about the OIC process but everyone makes it seem so complicated. How long did the whole process take from application to acceptance?

I did it myself, though I spent about 3 weeks researching and preparing before submitting. It's definitely complicated but doable if you're organized. The whole process took about 9 months from submission to final acceptance. The key was being extremely thorough with the financial information and documentation. I literally sent them a binder with everything tabbed and indexed. The IRS assigned an offer examiner who called me twice to clarify some expenses, but otherwise the process was mostly waiting. When I got the acceptance letter, I paid the agreed amount within a week, and they released the federal tax lien about 30 days later. Just be prepared for a lot of paperwork and patience!