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Something nobody mentioned yet - make sure you file even if you don't owe anything! I made that mistake one year thinking "I don't owe taxes so why file?" and missed out on getting my withholding back. You HAVE to file to get that money refunded to you. The IRS doesn't automatically send it back.
Is there a deadline for filing if you're owed a refund? I heard it's different than if you owe money.
You generally have 3 years from the original due date to file and claim a refund. So for 2025 taxes (filed in 2026), you'd have until April 2029 to claim your refund. After that, the money becomes property of the US Treasury and you can't get it back. But the deadline for filing if you OWE money is much stricter - you'll face penalties if you file late when you owe. That's why the distinction is important.
Hey I was in literally the exact same situation last year. Made 11k, had about $1200 withheld. I got ALL of it back plus some extra from tax credits. Filed in February and had my refund by mid-march. Just use a free filing service and it's pretty straightforward!!
Thanks for sharing your experience!! That's super helpful to know. Did you use one of the free file options on the IRS website or something else? And did you have to provide any special documentation since your income was below the standard deduction?
I used FreeTaxUSA which is one of the IRS Free File partners. Super simple interface and completely free for federal returns. You don't need any special documentation - just your W-2 form that your employer sends you by January 31st. The software automatically calculates whether you're below the standard deduction threshold and handles everything for you. Since your income is so straightforward (just W-2 wages), it should be really quick to complete!
Maybe Im just dumb here but im confused about something - if robinhood sent the 1099 to the IRS, wouldn't they have also sent it to your brother? Didn't he get any tax forms from them for 2021? Those forms should have all the info he needs to fix this
Robinhood sends tax forms electronically through their app/website. You have to log in to access them - they don't automatically mail them. A lot of people miss this and don't realize the forms are available. I made this exact mistake my first year trading.
This is exactly why I always tell people to be super careful with crypto taxes from day one. The IRS has been cracking down hard on unreported crypto transactions, and they have access to all the 1099 forms from exchanges. One important thing to add - when you file that amended return, make sure to include a detailed explanation letter with it. The IRS processors appreciate context about why you're amending, especially when there's such a big discrepancy. Something like "Originally failed to report cryptocurrency transactions due to misunderstanding of reporting requirements. Amended return includes complete Schedule D with all crypto transactions and correct cost basis." Also, don't panic about the timeline. You generally have 3 years from the original filing date to amend a return, so you're well within that window for 2021. The IRS will recalculate everything once they process your amendment, including removing those penalties and restoring the earned income credit. The good news is this is totally fixable, and you're definitely not the first person to go through this exact situation!
Really appreciate this detailed advice! The explanation letter is something I hadn't thought of - that's a great tip. Do you think it should be a separate document or can it be included somewhere on the actual 1040-X form? I want to make sure the IRS understands this was genuinely just a mistake and not intentional tax evasion. Also, you mentioned the 3-year window - does that clock start from the original filing date or the due date? My brother filed pretty close to the deadline that year so I want to make sure we're not cutting it close.
Has anyone actually succeeded with this strategy through an audit? I'm seeing lots of theory but wondering if there are success stories when the IRS actually reviews everything.
Yes, my brother-in-law successfully passed an audit while claiming real estate professional status with a W-2 job. The key was that he had negotiated his employment contract down to 15 hours weekly (documented), works remotely, and kept incredibly detailed records of his real estate activities including video logs of property visits and time-stamped communications with tenants/contractors. He also had a legitimate real estate business structure with separate bank accounts, business cards, website, etc. The IRS initially questioned his status but ultimately accepted it after reviewing his documentation. But he literally had 800+ pages of supporting documents!
This is fascinating but also terrifying! I'm a marketing director making $280k and have been considering real estate investing specifically for tax benefits. Reading about your colleague's $140k penalty really makes me pause though. I'm wondering - for those who've successfully navigated this, what's the minimum number of rental properties you'd recommend to realistically generate enough hours for REPS qualification? And has anyone tried the strategy of purchasing properties that need significant renovation work to legitimately rack up more documented hours? Also curious about the timing - if I start investing in real estate this year, can I claim REPS status immediately or do I need to establish a track record first? The documentation requirements sound intense but doable if you're organized from day one.
I'm using H&R Block software and they told me to copy the employer name EXACTLY as it appears on box e of my W-2, including Inc, LLC, Corp or whatever abbreviation is there. They said it needs to match the IRS records 100% or it could get flagged.
Thanks everyone for all the helpful advice! I just wanted to follow up on my original question. I ended up using the exact name from box e of my W-2, including the "INC" part, and my return was accepted without any issues. For anyone else dealing with this - I was overthinking it way too much. The key really is just copying whatever is printed on your W-2 exactly as it appears. Don't try to "clean it up" or make it look nicer - the IRS matching system expects it to be identical to what your employer reported. My refund is already processing, so I'm really glad I didn't second-guess myself and change anything. Sometimes the simplest approach is the right one!
Melina Haruko
Has anyone used both ProSeries and Drake tax software for their independent practice? I'm trying to decide which one to go with when I leave my firm.
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Dallas Villalobos
ā¢I've used both. Drake is more affordable ($1600ish vs $2500+ for ProSeries Professional) and has great customer support, but ProSeries has a slightly better interface and handles more complex returns more elegantly. If you're just starting out and watching costs, Drake is solid choice.
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Keisha Taylor
Your pricing strategy sounds reasonable for starting out! I made the transition from Block to my own practice three years ago, and one thing I learned is to be confident about your rates from day one. $125-130/hour is actually quite fair for the Chicago market, especially with your Jackson Hewitt experience. A few practical tips: Consider offering a free 15-minute initial call to discuss their needs - this helps you qualify clients and gives them confidence in your expertise. For that first consultation, prepare a structured agenda so you maximize the value you provide in that hour. I also recommend getting everything in writing with a simple consultation agreement that outlines what you'll cover. Don't forget to factor in your prep time when pricing - reviewing their documents beforehand often takes 15-30 minutes that you should account for. And definitely get comfortable talking about money upfront. Clients respect professionals who are clear about their fees and payment terms. Good luck with your new venture!
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