Do you remember approximately how long it took for the IRS to process your e-filed 1040-X through FreeTaxUSA? I've heard horror stories about paper amendments taking 6+ months, wondering if e-filing is significantly faster.

It took about 7 weeks from submission to getting my refund, which was significantly faster than paper filing. The IRS sent an acknowledgment of receipt within 2 days of e-filing, which gave me peace of mind that they actually had my amendment. From what I've heard, paper amendments are taking 6-12 months right now, so e-filing is definitely the way to go if you qualify. Just make sure your changes are for forms that support e-filing - not all schedules can be e-filed for amendments even now.

Actually this isn't always true. If you've had tax payments applied to the year in question after filing (like estimated tax payments that were applied forward or carryforwards from other years), the deadline can be extended to 2 years from the date of the last payment rather than 3 years from filing. Worth checking if this applies to your situation OP.

Quick question - does filing an extension for your original return extend the amendment deadline too? Like if someone filed a 2019 extension until October 2020, would they have until October 2023 to amend?

Thanks for the tip about entering them separately! Do you know if TurboTax will automatically ask me about the medical insurance exception, or do I need to look for that specifically somewhere?

TurboTax should ask you about exceptions after you enter each 1099-R form. When it asks about the distribution code (Box 7), it will then follow up with questions about your situation. If you indicate you were unemployed, it should specifically ask if you used any of the money for health insurance premiums. If it doesn't automatically prompt you, look for a section called "Exceptions to Tax Penalties" or something similar after entering your 1099-R information. Make sure you have documentation of your insurance premium payments during your unemployment period, as you'll need this if you're audited.

I used it last year for a similar retirement withdrawal situation. The expert was helpful in confirming I qualified for an exception to the penalty since I was using the money for health insurance during unemployment. For complex situations like multiple 1099-Rs with no W-2s, I'd say it's worth the extra cost for the peace of mind.

That's really good to know - my bankruptcy was discharged about 14 months ago, so sounds like I should be past that waiting period. I do have one tax return I haven't filed yet because I knew I'd owe and couldn't pay. Should I get that filed ASAP before contacting them about the Fresh Start options?

Yes, absolutely file that outstanding return immediately. The IRS won't even discuss resolution options until you're in compliance with all filing requirements. Even if you can't pay what you owe, getting the return filed is the necessary first step. Think of it this way - the IRS sees unfiled returns as someone trying to hide or avoid their obligations entirely, while someone who files but can't pay is at least being transparent about their situation. Once you've filed everything, then you can approach them about payment options through the Fresh Start program with a much better chance of success.

I think this depends on your specific situation though. The IRS doesn't actually expect you to create more debt (like maxing out credit cards) to pay tax debt. They look at reasonable collection potential. When I submitted my OIC, I just had to document my current financial situation honestly.

So if the W2 is wrong but the actual withholdings were correct all along, does the person need to do anything special when they file? Like report the discrepancy somewhere?

Once you receive the corrected W2-c, you just use that form instead of the original incorrect W2 when filing your taxes. You don't need to report the discrepancy or include any special forms explaining the situation. The corrected W2-c will show the original incorrect amounts, the correct amounts, and the difference between them. This makes it clear to the IRS what changed and why. Just make sure you're using the final corrected numbers when completing your tax return.

In my experience it took about 3 weeks. If it's getting close to the deadline you can always file for an extension to give yourself more time.

Thank you! My income is around $48,000 - would I still qualify for EITC? And my brother is still in high school, but I am paying for some tutoring services. Would those count as educational expenses?

With $48,000 income and two dependents, you should still qualify for some EITC, though not the maximum amount. The phase-out for Head of Household with two qualifying dependents starts higher than your income, but you'll get a partial credit. Every bit helps! For educational expenses, unfortunately tutoring for high school generally doesn't qualify for the education credits. Those are primarily for post-secondary education (college, vocational schools, etc.). However, if the tutoring is related to a medical condition and prescribed by a doctor, you might be able to count it as a medical expense instead.

This is super important! And just adding on - there's sometimes a gap between disability approval and Medicare coverage starting. During that time, look into if your state has a Medicare Savings Program that could help with premiums.