Anyone else worried about amendments increasing audit risk? I've always heard changing your return is like waving a red flag to the IRS.

Based on the amounts you mentioned ($4,800 in charitable donations + $2,300 in work expenses), you're definitely looking at a worthwhile refund if you were already itemizing in 2022. That's over $7,000 in additional deductions you left on the table. I'd recommend gathering all your documentation first - donation receipts, bank statements showing the charitable contributions, and any records of your work-from-home expenses. For home office deductions, you'll need to be able to demonstrate the space was used regularly and exclusively for work. The 1040-X isn't too intimidating once you get started. Since you used TurboTax originally, you might want to use their amendment feature to keep everything consistent. Just be prepared for the wait time - amended returns are definitely taking longer to process than regular returns right now, but the interest they pay on delayed refunds helps offset some of that inconvenience. Given the potential refund amount, I'd say it's absolutely worth your time to file the amendment!

As a newcomer to this community, I'm genuinely concerned after reading through all these responses. The legal and financial risks everyone has outlined are extensive and serious - from potential money transmitter violations to gaming law issues to platform terms violations. What strikes me most is how what seemed like a simple streaming concept has so many different regulatory pitfalls. The fact that multiple experienced members are independently raising red flags about federal law violations, state gambling regulations, and personal liability issues should be a major wake-up call. @KingKongZilla - I really hope you take the advice here seriously about consulting with gaming law and tax attorneys before continuing. The consensus seems clear that this activity could expose you to risks far beyond what any entertainment value or tips could justify. Even if you've been doing this for a while without issues, that doesn't mean you're in the clear - regulatory enforcement can happen at any time, and the consequences could be life-changing. It might be worth exploring completely different streaming content that doesn't involve handling other people's money for gambling. There are so many successful streamers who build audiences without taking on these kinds of legal and financial risks.

As a newcomer to this community, I'm struck by the comprehensive legal concerns that have been raised throughout this discussion. The unanimous warnings from experienced members about money transmitter laws, gaming regulations, and platform policy violations paint a picture of significant regulatory risk. What's particularly alarming is the potential for retroactive enforcement - even if @KingKongZilla stops this activity now, past transactions could still trigger investigations or penalties. The IRS, state gaming commissions, and federal agencies like FinCEN don't just look at current activity when they investigate potential violations. I'd strongly recommend not just consulting with attorneys, but also proactively reviewing all past transactions to understand your potential exposure. Consider whether you need to file any retroactive reports or disclosures to get ahead of potential issues. The cost of proper legal consultation now is likely far less than the penalties and legal fees you could face if regulatory agencies discover this activity on their own. The streaming entertainment value simply isn't worth the risk of federal prosecution, substantial financial penalties, or having multiple payment processors permanently ban your accounts. There are countless successful content creators who build audiences without handling other people's money for gambling - it might be time to pivot to a completely different streaming approach.

Pro tip: sign up for informed delivery with USPS. Sometimes you'll see the check image before it even arrives if they're mailing it instead of direct deposit

I got mine last year on a Saturday with USAA! But like others said, it really depends on your bank's processing schedule. The state probably sent it out, but your bank might hold it until tomorrow. Two months is rough though - hopefully it shows up soon! 🤞

Just a heads up - E-File isn't the only one doing this. I tried TurboTax, H&R Block, AND TaxSlayer this year and ALL of them pulled the same stunt. They advertise free filing but then find some obscure reason why your "situation" requires a paid upgrade. In my case, I had a Health Savings Account which apparently triggered the "you need our deluxe version" notification on all three platforms. It's absolutely ridiculous and should be illegal. The only truly free option I found was filing directly through the IRS Free File portal, but you have to qualify based on income.

This is exactly why I've started avoiding these "free" tax services altogether. The IRS really needs to crack down on these misleading advertising practices. When a company advertises "free filing" but then forces upgrades for basic tax situations, that's false advertising plain and simple. For what it's worth, I've had good luck with FreeTaxUSA - they're upfront about what's actually free (federal filing) versus what costs extra (state filing is like $15). No surprise upgrades or hidden fees. Their interface isn't as flashy as the big names, but at least they're honest about their pricing from the start. It's ridiculous that in 2025 we still have to jump through hoops and use workarounds just to file our taxes without getting scammed. The whole system needs an overhaul.

22 Has anyone here had the IRS actually question this kind of thing before? I'm curious how much they really care about a payment that's off by a few days across tax years. Seems like they'd have bigger fish to fry?

I've been through this exact scenario twice in my freelancing career, and the stress is real! Here's what I learned from my CPA: the "constructive receipt" rule is your friend here. Since your client initiated the wire transfer in 2024, that's when you technically "received" the payment, even if it doesn't show up in your account until January. The fact that your client is putting this on your 2024 1099 is actually the key piece here. Always match what's on your 1099 - if they report it as 2024 income to the IRS, you should report it as 2024 income on your return. This consistency is what the IRS really cares about. For documentation, keep that confirmation email from your client showing when they sent the wire, along with your bank statement showing when it actually arrived. This paper trail shows the timing wasn't under your control. I've never been questioned on this type of situation, but having the documentation gives you peace of mind. Don't panic about the underpayment penalties either - if your quarterly estimates were calculated in good faith based on expected 2024 income (including this payment), you should be fine. The IRS understands that wire transfers can have delays, especially around year-end.