Since u dont have to worry about penalties anymore, consider looking into short-term health plans to cover the gap between jobs. Way cheaper than COBRA. Just be aware they don't cover pre-existing conditions and aren't comprehensive like ACA plans. But for a few months of basic coverage against emergencies, it's better than nothing!

Great question! You're absolutely right - there's no federal penalty for not having health insurance starting from the 2019 tax year. However, I'd strongly recommend looking into your options during the gap period anyway. Since you mentioned you're between jobs, you might qualify for a Special Enrollment Period on healthcare.gov if you recently lost employer coverage. This could make marketplace plans more affordable than you think, especially if your income qualifies you for premium tax credits. Also consider that even a basic catastrophic plan could save you from financial disaster if something unexpected happens. Medical debt is still one of the leading causes of bankruptcy, even for people who thought they were being smart by saving the premium money. When you do start your new job, make sure to sign up for their health insurance right away during your eligibility period - don't wait for the next open enrollment!

Has anyone used TurboTax for this situation? I have similar negative/positive numbers on my Schedule D and I'm wondering if the software handles this automatically or if I need to manually override something.

I went through this exact same confusion last year! You're absolutely right to use -1,912 on Line 3 and keep the minus sign. I know it feels weird entering a negative number, but the worksheet is specifically designed to handle capital losses this way. What helped me understand it better was realizing that the Qualified Dividends and Capital Gain Tax Worksheet is trying to figure out how much of your income qualifies for the lower capital gains tax rates. When you have a net capital loss (like your -1,912), it essentially means you don't have capital gains to apply the preferential rates to, so the worksheet adjusts accordingly. The key thing to remember is that "smaller" in tax terms means the value that results in less taxable income at preferential rates, not necessarily the numerically smaller number. Your -1,912 is the correct entry, and the subsequent lines will handle the math properly to ensure you're not overpaying on your qualified dividends. Don't second-guess yourself - you've got it right!

I'm so sorry for your aunt's loss. This is such a challenging situation to navigate while grieving. One important resource that hasn't been mentioned yet is the IRS Taxpayer Advocate Service (TAS). Since your aunt has mobility issues and is dealing with a complex situation involving a deceased spouse, she may qualify for their assistance. TAS is a free service within the IRS that helps taxpayers resolve problems and navigate difficult situations. You can reach TAS at 1-877-777-4778, and they often can help expedite transcript requests or provide guidance on exactly what forms are needed in her specific situation. They're particularly helpful for taxpayers facing hardships, which certainly applies here. Also, if your uncle had any business income (Schedule C), rental properties (Schedule E), or investment accounts, those may require additional forms or have specific reporting requirements that could affect the final return. The transcripts will reveal these, but it's worth mentioning so you're prepared. One more practical tip: when your aunt signs the final joint return, she should use blue ink if possible. The IRS can better distinguish original signatures from photocopies, which can help avoid processing delays. Take care of yourselves during this difficult time. The tax situation will get resolved - focus on supporting your aunt through her grief as well.

I'm so sorry for your aunt's loss. Having been through this myself when my mother passed, I understand how overwhelming the tax situation can feel on top of everything else. One thing that really helped me was creating a simple checklist to work through systematically. Here's what I'd suggest for your aunt: **Immediate steps:** 1. Locate any 2023 tax documents she can find (W-2s, 1099s, previous year's return for reference) 2. File Form 4506-T requesting both Wage & Income Transcript and Account Transcript for 2023 3. Include a copy of the death certificate with the form to avoid delays **What to expect from the transcripts:** - Wage & Income Transcript will show all reported income (W-2s, 1099s, etc.) - Account Transcript will reveal any estimated payments, prior year balances, or payment plans **For the final return:** - File as "Married Filing Jointly" - Write "DECEASED" and date of death next to your uncle's name - In his signature area, write "Deceased [date]" - She signs normally in her area, adding "surviving spouse" The IRS processes transcript requests pretty quickly by mail (usually 5-10 business days), so she should have the information she needs soon. Once you see what income sources are listed, the picture becomes much clearer. Don't hesitate to call the Taxpayer Advocate Service at 1-877-777-4778 if you need additional guidance - they're specifically there to help in situations like this. You're being such a caring nephew/niece to help her through this difficult time.

I'm dealing with this exact same situation! Also went through my own "brilliant" day trading phase earlier this year and completely ignored keeping proper records. When I downloaded my Robinhood CSV file last week, I honestly felt like crying looking at hundreds of transactions with no organization whatsoever. This entire thread has been incredibly helpful and reassuring - it's amazing to see how many people have been through this same experience. Based on everyone's advice, I'm definitely convinced that trying to handle wash sales manually would be a complete disaster. I'm planning to go with TaxAct Deluxe after seeing multiple confirmations that it handles all the complex calculations correctly and matches 1099s perfectly. The $25 price point is so much more reasonable than TurboTax Premier, especially since we're already going to get hit with short-term capital gains taxes on most of these trades. The tax-loss harvesting advice before December 31st is something I really need to act on quickly. I'm also holding several positions that are still underwater from my trading spree, so strategically selling some of those losses could help offset my gains and reduce the overall tax impact. Thanks to everyone for sharing their experiences and making this feel manageable instead of completely hopeless! It's honestly such a relief to know I'm not the only one who learned this record-keeping lesson the hard way. Definitely going to be much more organized with tracking everything going forward!

I'm in the exact same situation and this thread has been such a lifesaver! I also went through a heavy trading period earlier this year without keeping proper records, and when I first opened my Robinhood CSV file I felt completely overwhelmed. After reading everyone's experiences, I'm definitely convinced that trying to do wash sale calculations manually would be a nightmare. I had no idea those rules were so complex until people started explaining them here - I definitely traded some of the same stocks multiple times within short periods. Based on all the recommendations, I'm planning to go with TaxAct Deluxe. The $25 price point is so much more reasonable than TurboTax Premier, and seeing multiple confirmations that it handles wash sales correctly and matches 1099s perfectly gives me confidence it's the right choice. The tax-loss harvesting deadline is something I really need to focus on before December 31st. I'm also holding several positions that are underwater from my trading spree, so being able to use those losses to offset my gains could significantly help with the tax situation. Thanks to everyone for sharing their experiences and making this feel manageable instead of completely hopeless! It's honestly so comforting to know I'm not the only one who learned this record-keeping lesson the hard way. Definitely going to be much more organized with tracking trades going forward!

This whole thread has been incredibly enlightening! I had a similar situation with my cousin from Germany who won about $15,000 across several Vegas casinos last year. We were completely confused about what to do since gambling winnings aren't taxed in Germany at all. After reading through all these responses, it's clear we need to be more proactive. The casino did withhold 30% from his biggest win, but he never filed anything and just assumed that was the end of it. Now I'm realizing he might actually be entitled to a refund under the US-Germany tax treaty, and we should probably get him an ITIN to file properly. One question I have - does anyone know if there are any amnesty programs or voluntary disclosure options for tourists who missed filing in previous years? It sounds like the enforcement is getting stricter with international information sharing, so I'd rather get ahead of this before it becomes a bigger problem.

This thread has been incredibly helpful! I'm a tax professional who works with international clients, and I want to emphasize a few key points that have come up here. First, the advice about being proactive is spot-on. The IRS has significantly expanded its international data sharing capabilities through programs like FATCA and various tax treaties. What might have gone unnoticed years ago is increasingly likely to be flagged now. For anyone in this situation, here's my recommended approach: 1) Apply for an ITIN immediately if you don't have one, 2) Gather all casino documentation (W-2G forms, receipts, etc.), 3) File Form 1040NR even if it's late - the IRS is generally more lenient with first-time foreign filers who are trying to comply, and 4) If your country has a tax treaty with the US, make sure to claim those benefits. The potential upside is significant - I've helped clients recover thousands in over-withheld taxes. The key is acting before the IRS contacts you, which puts you in a much stronger position for penalty abatement and demonstrates good faith compliance.