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Just a heads up that the 1099-B from your broker will break everything down and should include all the wash sale adjustments properly. They'll report both to you and the IRS. You'll get it around February. When you file your taxes, you'll report all of this on Schedule D and Form 8949. Most tax software can import all this directly from major brokers and will handle the calculations correctly.
This is mostly right but some brokers' 1099-Bs can still be confusing. My Etrade one last year showed the wash sales but didn't explain how they affected my final numbers. Had to spend hours figuring out what was happening.
I've been through this exact situation before! The key thing to understand is that disallowed losses from wash sales don't disappear - they get added to the cost basis of your replacement shares. So while your broker might show a net gain of $66,800, the actual taxable amount could be different once all wash sale adjustments are properly calculated. Here's what I'd recommend: First, try to identify all your wash sales manually if you can - look for any stocks you sold at a loss and then repurchased within 30 days. Second, don't rely completely on your broker's current gain/loss summary until you get your official 1099-B in February, as that's when everything gets properly adjusted. If you need a more accurate estimate now for planning purposes, consider using tax software or a service that can analyze your trades and account for wash sales properly. And definitely start setting aside money for taxes - short-term gains are taxed as ordinary income, so depending on your tax bracket, you could owe 22% or more in federal taxes alone.
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Has anyone used a third-party service to help with the ERO application? I'm in a similar boat and wondering if it's worth hiring someone or if I should just apply directly.
I used a tax attorney who specializes in IRS representation to help with my application because I had a more complicated situation (bankruptcy from 3 years ago). Cost me about $1500 but they handled everything and my application was approved without issues.
I actually went through this exact situation about 2 years ago with a DUI from 6 years prior. I was terrified that it would prevent me from getting ERO status, but it turned out to be much less of an issue than I expected. The key things that helped me were: 1) Being completely honest on Form 8633 - I disclosed everything upfront, 2) Including a brief letter explaining the circumstances and what I learned from the experience, and 3) Emphasizing my clean record and professional conduct since then. My application was approved without any follow-up questions. The IRS seems much more concerned with recent issues or patterns of behavior rather than isolated incidents from several years ago. Your 9 years of experience as a tax preparer with an active PTIN actually works strongly in your favor - it shows you've been trusted with tax preparation responsibilities and maintained good standing. Don't let the DUI stop you from pursuing your business goals. Just be honest, provide complete information, and let your professional track record speak for itself.
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Has anyone successfully gotten a waiver for multiple years of missed RMDs? My parents missed 2022 AND 2023 distributions from their IRAs (about $900 each year) and just realized it now. They've already taken both missed amounts out (in February 2024). Not sure if we should file separate 5329 forms for each year or combine everything.
You definitely need separate Form 5329s for each tax year. For 2022, you'll need to file a standalone Form 5329 since the regular tax return deadline has passed. For 2023, you can include it with their 2023 return if they haven't filed yet. Write "RC" next to Line 55 on both forms and include a detailed explanation letter for each year. Multiple years is tougher to get waived than a single missed year, but since they've already corrected by taking the distributions, they have a decent chance, especially if there were health issues or other reasonable cause.
I'm dealing with a similar situation but for my elderly father's 403(b) account. He missed his 2023 RMD of $2,400 and we just caught it last month. We've already taken the distribution to correct it. One thing I learned from our tax preparer is that you should also keep documentation showing when you took the corrective distribution - bank statements, 1099-R forms, etc. The IRS may ask for proof that you actually corrected the mistake, especially if there's a gap between when you missed the RMD and when you took it. Also, if your RMD was calculated based on December 31, 2022 account balance, make sure that calculation was correct in the first place. Sometimes people think they missed an RMD when actually their calculation was wrong and they didn't owe one. Worth double-checking the IRS life expectancy tables to be sure. The $67.50 penalty you calculated sounds right (10% of the shortfall), but definitely go with the $0 on Line 55 approach that others have mentioned. First-time missed RMDs with reasonable cause explanations get approved for waivers most of the time.
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If you electronic file these days you don't even need to mail in your W-2s anymore. The IRS already has that information from your employer. You just need to make sure the numbers you enter match what's on your W-2. Maybe this is a sign to switch to e-filing?
Wait, really? I had no idea the IRS already has my W-2 info. Does that mean I don't need to mail anything in at all? This is my first time doing my own taxes so I'm really confused about the whole process.
Yes, absolutely! Your employer sends a copy of your W-2 directly to the IRS, so they already have that information in their system. When you e-file, you just enter the information from your W-2 into the tax software, and the IRS will match it with what they have on file. For most people with straightforward tax situations, there's no need to mail anything physical to the IRS when you e-file. You just keep your W-2s and other tax documents for your records. E-filing is faster, you get confirmation when the IRS receives and accepts your return, and refunds typically come much quicker too.
Pro tip: Always make copies or scan important tax documents before sending anything to the IRS! I learned this the hard way years ago. Now I have a digital folder for each tax year with scans of all my documents.
What's the easiest way to scan these docs if you don't have a scanner? Just take pics with your phone?
Yes! Phone cameras work great for this. Most phones have a "document" or "scan" mode in the camera app that automatically adjusts the lighting and makes the text clearer. You can also use apps like CamScanner or Adobe Scan that will convert your photos to PDF format and clean them up automatically. Just make sure the lighting is good and all the text is readable before you save it.
Madison Tipne
Everyone keeps talking about FreeTaxUSA and TurboTax, but I've been using Credit Karma Tax (now Cash App Taxes) for the past 3 years and it's completely free for federal AND state filing. It handles child tax credits, mortgage interest, and even small business income. I have 2 kids and it was super easy to enter their information and get the child tax credits. Might be worth looking into since you mentioned wanting to save money. The interface is pretty straightforward too.
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Holly Lascelles
•Does Cash App Taxes offer any kind of support if you have questions during the process? I'm worried about getting stuck halfway through with no one to ask for help.
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Madison Tipne
•Cash App Taxes does offer customer support, but it's more limited than some paid options. They have email support and an online help center, but no phone support or live chat. If you're worried about getting stuck, TurboTax Live or H&R Block's online assist options would give you more support, though they cost more. In my experience, the interface is pretty intuitive, and their help articles cover most common questions. I did have one question last year about reporting some stock sales, and they responded to my email within about a day. For straightforward returns with W-2 income and child tax credits, you probably won't need much support.
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Malia Ponder
Just wanted to add one more option to consider - I've been using FreeTaxUSA for 3 years after switching from TurboTax, and it's saved me hundreds. But this year I also discovered Tax Hawk, which is actually made by the same company as FreeTaxUSA but has a slightly different interface and sometimes different promos. For what it's worth, I have a pretty similar situation (married, 3 kids) and FreeTaxUSA worked great for claiming all the child tax credits correctly. The step-by-step guidance is really clear, and I never felt like I was missing anything important.
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Kyle Wallace
•Thanks for mentioning Tax Hawk! Question - do you know if any of these services can handle a situation where custody of kids is split? My ex and I alternate years for claiming our kids on taxes.
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Ella Cofer
•Yes, both FreeTaxUSA and Tax Hawk can definitely handle split custody situations! When you're entering dependent information, there's a section where you can specify whether you're claiming the child for the tax year or not. The software will ask you questions about custody arrangements and guide you through the rules about who gets to claim the child tax credit in alternating years. Just make sure you and your ex are coordinating properly about who's claiming which kids for which year - the IRS will flag it if both parents try to claim the same child. I'd recommend keeping some kind of written record of your agreement about alternating years, just in case there are ever any questions down the road.
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