This extension is such a relief! I was scrambling to get everything organized for my small business taxes - between all the receipts, mileage logs, and client payments, April 15th was looking impossible. The extra month gives me time to actually review everything properly instead of rushing and potentially missing deductions. Quick question for anyone who knows - does this May 17th deadline also apply to quarterly estimated tax payments for Q1 2025, or is that still due April 15th? I've been making quarterly payments for my freelance work but want to make sure I don't miss that deadline while focusing on getting my 2024 return filed.

This is such welcome news! As someone who's been putting off organizing my tax documents (guilty as charged), this extension feels like a lifesaver. I've been dreading dealing with the crypto transactions I made last year - trying to figure out cost basis and all those different trades has been overwhelming. The extra month will let me actually sit down and go through everything methodically instead of just throwing numbers together at the last minute. I'm also relieved to hear that the payment deadline is extended too, not just the filing deadline. Last year I had to scramble to come up with the money I owed by April 15th, so having until May 17th for both filing AND payment takes a lot of pressure off. Does anyone know if this extension affects state taxes too? I know some states follow federal deadlines automatically but others don't. I'm in California and want to make sure I'm not missing anything there.

Has anyone actually had the IRS question their return over this specific issue? I have the same problem with my W-2 but I'm wondering if it's worth the hassle of getting a corrected form if the IRS doesn't typically flag this.

This is exactly why proper W-2 reporting is so important! I work in tax preparation and see this mistake frequently. Your employer definitely needs to issue a corrected W-2 because the IRS computers are programmed to flag dependent care FSA amounts over $5,000 in Box 10. The transportation benefits should have been handled completely separately - they reduce your taxable wages in Box 1 but don't belong in Box 10 at all. When you contact HR again, you can reference IRS Publication 15-B which clearly states that qualified transportation fringe benefits are reported differently than dependent care assistance. If you're filing soon and can't wait for the correction, you could file with Form 8862 attached explaining the employer error, but getting the corrected W-2 is definitely the cleaner approach. Don't let them tell you it "doesn't matter" - it absolutely does for IRS matching purposes.

Am I the only one who thinks it's absolutely ridiculous that Robinhood references boxes that don't exist on their actual forms?? Every year I go through this same confusion. Why can't they just format their 1099bs like everyone else??? Or at least include a guide that matches THEIR form instead of some standard form they don't actually use!

I completely understand your frustration with the Robinhood 1099-B format! I went through this exact same issue this year and it drove me crazy too. After digging through everything, I finally figured out that what they call "box 12" is actually the "Basis Reported to IRS" information that appears in the transaction details section as a Y/N column. The key thing to understand is that Robinhood consolidates everything into their own format instead of using the traditional 1099-B layout with numbered boxes. When tax software or instructions reference "box 12," they're asking whether your cost basis was reported to the IRS - which you can find by looking at that Y/N indicator column in your transaction details. If you see mostly "Y" entries, it means Robinhood reported your cost basis to the IRS and you can use their numbers directly on Schedule D. Just make sure to also account for any wash sale adjustments that are shown in another column. Hope this helps clear up the confusion!

Something nobody mentioned - check if any of those investments could be considered qualified education expenses in the coming year. If your daughter is starting college, you might be able to time selling some investments with paying tuition and have them count toward education tax benefits like the American Opportunity Credit.

One thing to consider that might help with timing - if your daughter will be 18 during 2025 and truly providing more than half of her own support through work/internships, you could potentially avoid kiddie tax entirely by waiting. But be careful about the "more than half support" test - it includes tuition, room, board, everything. Also, don't forget about gift tax implications if you're funding her investment account. The annual exclusion is $18,000 for 2024, but if this account has grown from gifts over the years, make sure you're tracking that properly. Another strategy: if she has any investments that are currently at a loss, consider harvesting those losses this year to offset some of the gains. Even though she's subject to kiddie tax, capital losses can still offset capital gains dollar-for-dollar before the kiddie tax calculation even comes into play.

Just a heads up - I lived in Korea for 12 years and moved back to the US last year. Korean banks will also want your father to file a W-8BEN with them to claim the reduced treaty rate on any interest earned from Korean accounts. Otherwise, Korean financial institutions will withhold at their domestic rate (around 15.4% currently). It's a two-way street with these treaties - he needs to claim the treaty benefits with BOTH the US and Korean tax authorities. Also, make sure he's reporting any Korean bank accounts on FBAR if the aggregate total exceeds $10,000 at any point during the year. The penalties for missing that are brutal!

This is a complex situation that involves multiple layers of US tax compliance. Based on what you've described, your father needs to address several critical issues beyond just the treaty benefits: 1. **Formal expatriation process**: Since he's been a green card holder for 30 years, he needs to file Form I-407 to abandon permanent resident status and Form 8854 for expatriation tax purposes. The exit tax provisions could apply given his long-term resident status. 2. **Treaty benefits**: Yes, Article 13 of the US-Korea tax treaty does provide for a reduced 12% withholding rate on interest income instead of the standard 30%. He'll need to file Form 1040-NR and Form 8833 to claim these benefits. 3. **Korean tax obligations**: Don't forget he may also have Korean tax filing requirements as a returning resident. Korea generally taxes worldwide income for residents. 4. **FBAR reporting**: If he maintains US bank accounts or investments totaling over $10,000, he'll need to file FBAR (FinCEN Form 114) annually. Given the complexity and potential penalties involved (especially with expatriation requirements), I'd strongly recommend consulting with a tax professional who specializes in international tax and expatriation before filing anything. The costs of professional help will likely be far less than potential penalties for non-compliance.