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Another option you might consider - check if your wife's mom received a physical copy of the 1095-A in the mail. Sometimes people miss these forms in their mail since they look like regular healthcare notices. The marketplace typically mails them out by late January/early February. Also, if you can't get the form in time, you could file an extension to give yourself more time to track it down. Just remember an extension to file isn't an extension to pay, so you'd still need to estimate and pay any taxes due by the regular deadline.
Good point about checking the mail more thoroughly. I'll ask her mom to look through her papers again. Do you know if filing an extension is complicated? We've never done that before and I'm worried about messing something else up.
Filing an extension is actually very simple. You just need to submit Form 4868 which you can do electronically through most tax software or the IRS Free File. It automatically gives you until October 15th to file your complete return. The tricky part is estimating any taxes you might owe, since you'll still need to pay by the regular April deadline to avoid penalties and interest. Since your issue is just missing a form rather than not knowing what you owe, you could complete your return as best you can to estimate your tax liability, then pay that amount when filing the extension.
Just wanted to point out something important - if your wife was covered under her mom's marketplace plan, but her mom claimed the premium tax credit, you actually DO need to report this on your taxes. This is because the IRS needs to verify that everyone who received subsidized coverage is accounted for across all tax returns. It's confusing because your wife was on her mom's plan, but since you're filing a separate return from her mom, the IRS system flags the disconnect when it doesn't see the 1095-A information on your return.
This is exactly right. I work with tax issues, and this marketplace coverage reporting requirement trips up so many people. The system is designed to track premium tax credits at both the subscriber level (mom) and the covered individual level (wife) across returns.
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Another option worth exploring is contacting your state's unemployment office. Sometimes they have employer information on file even when the IRS transcript is incomplete. I had to do this when filing back taxes from 2018, and the state labor department had the EINs for two companies that had gone bankrupt. Also, if your friend contributed to a 401k during that time, the plan administrator might have records with the employer information. Same goes for any health insurance he had through those employers - the insurance company may still have the employer EIN on file.
Chloe Martin
ā¢Thank you for this suggestion! I didn't even think about checking with the state unemployment office. He did have health insurance through one of the jobs so we'll definitely reach out to the insurance company as well. Do you remember what department specifically you had to contact at the state level? Was it just the general unemployment office or did you have to ask for a specific record-keeping division?
I contacted the wage record unit within the state's Department of Labor. Most states have a division that handles wage reporting from employers for unemployment tax purposes. Just call the main unemployment office number and ask to be directed to whoever maintains employer wage records. For the health insurance angle, you'll want to contact the member services department and explain you need the employer information for tax purposes. Sometimes they'll need a written request, but in my experience, they were pretty helpful once I explained the situation.
One thing nobody's mentioned yet - you should consider the statute of limitations for refunds when filing back taxes. If your friend is owed money from the IRS for 2020, he needs to file before April 2024 (3 years from the original due date) or he loses that refund forever! But if he OWES money, there's no time limit for the IRS to collect, so he definitely needs to get this sorted. Also, penalties and interest keep accruing the longer he waits to file.
Actually the deadline for 2020 refunds would be May 17, 2024, since the IRS extended the filing deadline that year because of covid. But your point is totally valid - time is running out to claim any refund from 2020!
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For anyone considering DIY filing, I built a simple spreadsheet that helped me track everything for my ERTC claim. It has separate tabs for each quarter, wage calculations, PPP allocation, and the revenue comparison test. Happy to share if anyone wants it - just DM me. The whole process took me about 3 weekends to complete, but I saved around $32,000 compared to what a "specialist" company wanted to charge me. The IRS isn't processing these quickly (took 11 months to get my refund), but it was worth the wait.
Natalie Wang
ā¢Would love to see your spreadsheet! I'm just starting the process and feeling overwhelmed by all the calculations.
Noah Torres
Does anyone know the deadline for filing these ERTC claims? I heard it was extended but not sure until when.
Chloe Green
ā¢For most businesses, you can amend payroll tax returns (Form 941-X) up to 3 years after the original filing date. So for 2020 Q2, if you filed on July 31, 2020, you have until July 31, 2023 to amend. For 2021 Q3 (the last eligible quarter), most businesses will have until October/November 2024 to file claims. The IRS did implement a moratorium on processing new claims from September 2023 to early 2024 due to fraud concerns, but they're processing claims again now. Just be aware that processing times are extremely long - currently 10-12 months is common.
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Maya Jackson
One thing I haven't seen mentioned yet is the holding period requirements for ESPP shares. Based on your dates (acquired 6/15/2018, sold 4/12/2021), you've met the long-term holding period requirements, which is good. If you had sold within 1 year of purchase or within 2 years of the offering date (when your ESPP purchase period began), it would be considered a "disqualifying disposition" which has different tax implications. In that case, you might have had to report additional ordinary income. Since you held the shares for nearly 3 years, you've met both holding period requirements, so you should only need to worry about the cost basis adjustment everyone's talking about. Just make sure you classify it correctly as long-term capital gains on your 8949.
Leo McDonald
ā¢Thank you for bringing that up! I was worried about the holding period but wasn't sure what the requirements were. It's good to know I'm in the clear for long-term capital gains treatment. Question: Does the adjusted cost basis calculation change at all based on meeting the holding period requirements? Or is it still just adding back the ESPP discount amount that was already included in my W-2?
Maya Jackson
ā¢The adjusted cost basis calculation remains the same regardless of whether you met the holding period requirements. You still need to add back the discount that was included in your W-2 income. The holding period just affects how the gain is classified (long-term vs. short-term) and whether you might have additional ordinary income to report. With a qualifying disposition like yours, you only have the capital gain to worry about (proceeds minus adjusted basis). The fact that you held the shares long enough simplifies things because you'll get the lower long-term capital gains tax rate on your profits.
I've been doing my taxes for years and ESPP reporting is consistently one of the most confusing things. Here's a simplified way to think about it that helped me: 1. When you buy ESPP shares at a discount, that discount is considered compensation (essentially like a bonus from your employer) 2. Your employer includes this "bonus" in your W-2 income the year you purchase the shares 3. When you later sell those shares, you need to increase your cost basis by that "bonus" amount to avoid being taxed twice 4. On Form 8949, you list what's on your 1099-B, then use code B to adjust the basis My tax software (FreeTaxUSA) actually has a specific section for ESPP sales that walks through this calculation. I switched to it after TurboTax kept calculating my ESPP sales incorrectly.
Amaya Watson
ā¢Does FreeTaxUSA really handle this well? I've been using H&R Block online and it's completely confusing for stock sales. I have to manually override everything. Might switch if there's something that handles ESPP sales better.
Finnegan Gunn
Just be careful about what you mean by "selling" your crypto. If you're selling on a centralized exchange, that's pretty straightforward. But if you're swapping one crypto for another (like trading your underwater coin for a stablecoin), that's still a taxable event. Also make sure you're accounting for fees in your cost basis calculations. I messed this up last year and had to file an amended return when I realized I hadn't included gas fees in my cost basis, which meant I overpaid on taxes.
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Miguel Harvey
ā¢What about if you swap to a different crypto and then immediately back? Like ETH to USDT and then back to ETH? Does that still count as a valid loss?
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Finnegan Gunn
ā¢Yes, that absolutely counts as a valid loss (or gain). Each conversion is a separate taxable event. So if you go from ETH to USDT and recognize a loss, and then from USDT back to ETH, those are two distinct transactions. The IRS doesn't care what you do with the proceeds after you sell, they just care that you're reporting each taxable event. This is actually why crypto can be such a tax nightmare - every single swap, conversion, or trade is a reportable event, not just when you cash out to fiat.
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Ashley Simian
I'm curious if anyone knows - do different states handle crypto tax losses differently? Like, I know the federal limit is $3k per year for writing off losses against ordinary income, but do some states have different rules?
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Oliver Cheng
ā¢Most states follow federal treatment, but there are exceptions. For example, Nevada, Wyoming, and South Dakota have no state income tax so it's not an issue there. New Jersey doesn't allow carrying forward capital losses like the federal government does. Always worth checking your specific state's rules.
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