Can I piggyback on this question with a related margin interest issue? If I use margin to buy both stocks and options, but only sell the options for a profit while keeping the stocks, can I deduct all the margin interest? Or only the portion related to the options I sold?

Just wanted to add a practical tip from my experience with a similar situation. When you're preparing your taxes, make sure you have good documentation of all your margin interest payments throughout the year. Your brokerage should provide this on your 1099-INT or in your monthly statements, but it's worth double-checking the totals. Also, keep in mind that if you have multiple brokerage accounts, you'll need to aggregate all your investment income and all your investment interest expenses across all accounts when completing Form 4952. The IRS looks at your total investment picture, not account by account. One more thing - if you're planning to continue using margin in future years, consider keeping a spreadsheet to track your margin interest payments monthly. This makes tax prep much easier and helps you project whether you'll have enough investment income to fully deduct the interest each year.

Just wanted to mention that you can actually e-file past year returns using some tax software, which is WAY easier than paper filing. I used FreeTaxUSA for my 2020 return when I filed in late 2023. They charge like $20 for past year returns but it was totally worth it to avoid the paper forms nightmare.

I'm going through a very similar situation right now with my 2020 taxes! Lost my job in March 2020 and honestly just couldn't deal with paperwork for the longest time. I finally gathered all my documents last month and realized I might actually owe money despite having taxes withheld from my W-2. One thing that really helped me was calling the IRS Taxpayer Advocate Service (TAS) - they're a separate division that helps people with complex tax problems for free. They don't file your return for you, but they can explain your options and help you understand what penalties you might face. The number is 1-877-777-4778. They were way more patient and helpful than trying to navigate the regular IRS phone system. Also, don't panic about the penalties if you do owe. The failure-to-file penalty stops accruing after 5 months, so it maxes out at 25% of what you owe. The failure-to-pay penalty continues but it's only 0.5% per month. Still not great, but not as scary as it sounds when people say "penalties keep growing forever.

For anyone in this situation, please remember that if your income was only $14k in 2023, you were probably under the filing requirement threshold anyway! For 2023, single filers under 25 didn't need to file if they made less than $12,950.

Don't feel embarrassed at all - you're definitely not alone in this situation! I work as a tax preparer and see people in similar circumstances all the time. The good news is that with your income level of $14,000, you're almost certainly due a refund rather than owing anything. Here's what I'd recommend: First, gather your 2023 W-2 from the coffee shop (contact them if you can't find it - they're required to provide copies). Then you have a few options - you can use free tax software like the IRS Free File program, visit a VITA (Volunteer Income Tax Assistance) location for free help, or even just fill out a simple 1040 form. The key thing is that there's no penalty for filing late when you're due a refund. You have until April 15, 2027 to claim your 2023 refund, so you've got plenty of time. Once you file, you'll probably get back most or all of what was withheld from your paychecks, and you might even qualify for the Earned Income Tax Credit which could mean extra money back. You're taking the right step by asking for help - don't let tax anxiety keep you from claiming money that's rightfully yours!

Does anyone know if the financial institution you transfer the inherited 401k to matters? I've heard some places handle stretch IRAs better than others since the SECURE Act changes. I'm in a similar situation where I qualify as an eligible designated beneficiary (I'm disabled) but worried about choosing the right place to transfer my late husband's 401k.

I'm dealing with a very similar situation and wanted to share what I learned from my estate attorney. Since you're older than the original 401k owner, you definitely qualify as an "eligible designated beneficiary" under the SECURE Act exception for individuals not more than 10 years younger than the decedent. One thing that hasn't been mentioned yet - make sure when you do the rollover that it's titled correctly as an "inherited IRA" with both your name and the deceased's name (something like "Kaitlyn Otto as beneficiary of [deceased's name] IRA"). This is crucial for maintaining the tax-deferred status and ensuring you can take the stretch distributions properly. Also, since the original owner passed in 2022, you should have already started taking RMDs by December 31, 2023. If you missed that deadline, you may need to file Form 5329 to request a waiver of the 50% penalty, but the IRS has been more lenient with inherited account penalties during the transition period after the SECURE Act. I'd strongly recommend getting everything documented before you approach the financial institution, because as others have mentioned, many of them are still learning these rules themselves.

Protip: Stop checking WMR its garbage. Transcripts are the source of truth for everything tax related

Just wanted to chime in as someone who went through this exact same thing last year! The 846 code is definitely what you want to see - that's the IRS saying "we're sending your money." WMR is notorious for being slow to update and honestly kind of unreliable. I've seen people get their refunds while WMR still showed "accepted" for days afterward. Trust your transcript over WMR every time!