Thanks for mentioning this! I did have marketplace insurance in 2022 I think. Where exactly do I find those forms if I can't log into my old account?

If you can't access your marketplace account, you can call the marketplace directly at 1-800-318-2596 and request that they resend your 1095-A forms for the years you need. Make sure to have your personal information ready (SSN, DOB, address from that time). Alternatively, you might be able to get the information from the IRS by requesting a tax transcript, though sometimes these forms don't show up completely on the transcript. The best route is definitely going directly through the marketplace if possible.

How do you find someone who specializes in unfiled returns? Just search for "tax resolution" or is there some specific credential I should look for?

14 Could you explain more about this "step-up in basis" for inherited annuities? I thought that only applied to things like stocks and real estate, not annuities. Does it depend on when the original owner passed away?

20 The step-up in basis rules are complicated for annuities and depends on several factors. Generally, annuities don't receive the same full step-up in basis that other inherited assets might get. With annuities, what typically happens is that the income tax treatment passes to the beneficiary. So the taxable portion is still generally the difference between what was paid into the annuity (the cost basis) and its value at distribution. The step-up that can sometimes apply relates to the value at the date of death versus the original purchase price, but this varies based on how the annuity was structured and when the death occurred.

17 I tried that first actually! The customer service rep I spoke with just kept repeating that they "cannot provide tax advice" and directed me to consult a tax professional. Super frustrating experience.

Technically that would be tax fraud lol. But realistically you're right, nobody would ever notice or care about 6 cents. Still, I'd probably report it just to avoid any potential matching issues if the employer submitted it to the IRS.

Haha true about the tax fraud thing, but I wonder if there's actually a minimum threshold where the IRS just doesn't care. Like if you found a penny on the ground, you technically earned income but nobody reports that. I guess the difference is that this has an official W2 attached to it that's already in the system. You're right that reporting it is probably best just to keep everything matched up in their systems.

Box 14 is for "other" information that employers want to report but doesn't fit in the standard boxes. It could be union dues, health insurance premiums, educational assistance, or a bunch of other things. Usually not taxable, which might explain why Box 1 is empty - there were no taxable wages.

Is audit protection even worth it? What does it actually do for you if you get audited?

Audit protection isn't legal representation, but it typically provides guidance through the audit process. For FreeTaxUSA, their "Audit Assist" gives you access to tax professionals who will answer your questions and help you understand what documents you need and how to respond to IRS notices. TaxAct's protection is similar, but in my experience, their customer service is generally less responsive. Neither service will represent you before the IRS - for that you'd need a CPA or tax attorney. It's basically paying for a helpline if you get audited.

Did you have to pay anything extra for the 1099 forms specifically with TaxAct? Their website isn't super clear about whether Schedule C is included in the free version.

1 I actually don't have an accountant yet - part of why I'm in this mess! Been trying to handle everything myself to save money in the first year, but clearly that's not working out so well. Do accountants typically take on new clients same-day when there's a deadline?

3 Many accountants do offer same-day extension filing for new clients, especially during tax season. It's a common way they begin relationships with new business clients who are in a bind. A simple extension filing is low-risk for them and gives you both a chance to work together. I'd recommend calling a few local business accountants and explaining your situation. Be clear that you need the Form 7004 filed today and ask if they can help. Even if they can't take you on as a full client right away, many will handle just the extension filing to help you meet the deadline.

1 Oh crap, I didn't realize that! I haven't calculated what I might owe yet. Is there a quick way to estimate this, or do I need to basically do all the tax calculations anyway?

14 You don't need to do the complete calculations, but you should make a reasonable estimate based on your business income and expenses for the year. A safe approach is to look at what you paid last year (if you were in business) and pay at least that amount. If this is your first year, calculate your rough profit and multiply by the appropriate tax rate. If you're really unsure, it's generally better to overpay slightly and get a refund later than to underpay and face penalties. Even a good faith estimate shows the IRS you're trying to comply, which can help if you end up slightly short.