I went through a very similar situation when I got laid off but had significant investment income! Here are a few key points that helped me navigate it: **You definitely need quarterly payments** - With $70K in capital gains plus $15.6K in annual dividends, you'll almost certainly owe more than the $1,000 threshold that triggers estimated payment requirements. **Consider the timing** - Since your capital gains were a lump sum, you might benefit from using the "annualized income installment method" rather than equal quarterly payments. This lets you pay more in the quarter when you actually realized the gains and less in other quarters. **Don't forget state taxes** - Most states have their own estimated payment requirements that may differ from federal rules. Make sure to research your state's specific thresholds and due dates. **Safe harbor strategy** - Since you were employed part of the year, calculate both options: paying 100%/110% of last year's total tax (safe harbor) versus paying based on this year's actual expected income. Sometimes safe harbor is actually cheaper, especially if your employment income was significant before the job loss. **Set aside money NOW** - I'd recommend immediately moving at least 25-30% of your capital gains to a separate savings account. Better to have too much set aside than scramble for payment money later. Given the complexity and amounts involved, a consultation with a tax professional would be money well spent. Even one session can help you set up a proper payment strategy and avoid costly mistakes. Good luck!

I've been following this thread closely since I went through something very similar last year - lost my job but had substantial investment gains that created a whole new world of tax obligations I'd never dealt with before. One thing I don't think has been mentioned yet is the importance of keeping detailed records of WHEN during the year you realized your gains and received your dividend payments. This becomes crucial if you end up using the annualized income installment method that several people have mentioned. For example, if your $70K capital gains all happened in Q2, you might be able to make a smaller payment for Q1 since you hadn't actually earned that income yet. The IRS allows you to calculate payments based on your actual income timing rather than assuming it was earned evenly throughout the year. Also, since you mentioned being comfortable with TurboTax, they actually have a pretty decent estimated tax worksheet in their online tools that can help you run different scenarios. It's not a replacement for professional advice given your amounts, but it's a good way to get ballpark figures and understand how different calculation methods affect your required payments. One last tip: if you do decide to work with a tax professional, try to find someone who has experience with investment income and unemployed taxpayers. The combination creates some unique planning opportunities (like potentially being in a lower tax bracket this year) that not all preparers are familiar with. You're asking all the right questions, and it sounds like you're taking a smart approach by seeking advice before making any payments. Better to get it right from the start than try to fix mistakes later!

Has anyone dealt with a situation where they owned two properties simultaneously? I'm a consultant who splits time between two states about 50/50, own homes in both places, and I'm trying to figure out which one would qualify as my "primary" for Section 121 purposes.

Based on your situation, you have a very good chance of qualifying for the Section 121 exclusion. The key factors working in your favor are that you've maintained all official ties to the property (mail, voter registration, tax returns) and it's your only owned residence. The IRS recognizes temporary absences, even extended ones, as long as there's intent to return. Your digital nomad lifestyle doesn't automatically disqualify you - many people travel extensively while maintaining primary residence status. The fact that you've kept most belongings there and maintained it as your legal address are strong indicators of primary residence. However, I'd strongly recommend documenting everything that connects you to that address before you sell. Keep records of your voter registration, tax filings, bank statements, insurance policies, and any other official documents tied to that address. This documentation will be crucial if the IRS ever questions your claim. One potential complication is the partial rental situation you mentioned in the comments. Make sure you're properly accounting for any rental income and be prepared to allocate the exclusion based on the percentage of the home used for personal versus rental purposes. But this shouldn't disqualify you entirely - just affects the calculation. Given the complexity and potential tax savings involved, it might be worth consulting with a tax professional who can review your specific situation and ensure you're maximizing your exclusion while staying compliant.

I'm confused about one thing - if the gross distribution wasn't taxable, does that mean you never got the money? I have a similar situation with an old 401k.

Just to add some reassurance here - I work in retirement plan administration and see these situations all the time. When you left your previous employer, if your 401(k) balance was relatively small (usually under $5,000), the plan administrator likely executed what's called a "force-out" rollover. This means they automatically moved your funds to an IRA to reduce administrative costs for the plan. The fact that you have both code G and code H suggests you might have had both traditional pre-tax contributions and Roth after-tax contributions in your old 401(k). The traditional portion would have gone to a traditional IRA (code G) and the Roth portion to a Roth IRA (code H). You should have received notices about this rollover, but they might have gone to an old address. I'd recommend checking with companies like Fidelity, Vanguard, or Charles Schwab to see if they have any accounts in your name that you weren't aware of. Many force-out rollovers end up with these large providers. Since the taxable amount is $0, you really don't need to stress about amending your return. The IRS gets the same 1099-R you received and their systems can see it was a non-taxable rollover.

This is such a frustrating situation that shouldn't happen but unfortunately does all the time! I went through something very similar two years ago with a different company. Here's my advice based on what worked for me: First, definitely try calling the company's accounting department (not HR) and ask them to issue a corrected 1099-MISC showing $0. Explain that this was a pure expense reimbursement, not compensation. Some companies will cooperate, especially if you can speak directly with their AP manager or controller. If they won't budge, you have a few options for handling it on your return. The cleanest approach is to report the 1099-MISC income on Schedule 1 but then take an offsetting deduction on the same schedule under "Other Adjustments" with a clear explanation that this was reimbursement for actual expenses. Attach copies of your receipts and a brief statement explaining the situation. Whatever you do, don't just ignore the 1099-MISC - the IRS will definitely notice if you don't report income that was reported to them. But you absolutely shouldn't have to pay tax on money that was just reimbursing your actual out-of-pocket costs. Keep all your documentation and be prepared to explain the situation if questioned.

I'm dealing with a very similar situation right now! My husband had job interviews with two different companies last fall, and both reimbursed him for travel expenses. One company handled it correctly and didn't issue any tax forms, but the other one just sent us a 1099-MISC for $890. Reading through all these responses has been super helpful. I think I'm going to try calling their accounting department first to see if they'll correct it, but if not, the approach of reporting it on Schedule 1 and then taking the offsetting deduction with documentation seems like the way to go. One thing I'm wondering though - since this was for a job in the same field my husband currently works in, would these expenses potentially qualify as job search expenses once the miscellaneous deduction suspension ends in 2026? Or is the reimbursement/offsetting deduction approach always the better way to handle it regardless of the job search deduction rules? Thanks everyone for sharing your experiences - it's really reassuring to know this isn't just us dealing with this confusing situation!

I went through something very similar with my son last year when he worked at a Pizza Hut for just a few days. Here's what ended up working for us: First, definitely start by calling the specific Taco Bell location where she worked. Even if she was only there 3 days, they're legally required to provide a W2 if any wages were paid. Ask for the manager and explain the situation - sometimes W2s get returned to sender if there was an address issue. If the local store can't help, try the corporate route. Since Taco Bell is owned by Yum! Brands, you can contact their employee services. Many locations also use ADP or another payroll company, so ask the store who handles their payroll processing. One thing that really helped us was having my son's employee ID number and exact dates of employment ready when making these calls. If she has any paystubs, that information should be on there. The IRS deadline for employers to send out W2s was January 31st, so at this point Taco Bell is actually late in providing it. If you don't get anywhere with the employer by next week, definitely contact the IRS directly. They can intervene on her behalf and often that gets employers to act quickly. Even though it's a small amount, it's worth getting the proper W2 rather than estimating on Form 4852 if possible. Good luck!

I work in tax preparation and see this situation frequently with short-term employment. Here's the most efficient approach I recommend: 1. **Start with the store directly** - Call the specific Taco Bell location and ask for the general manager. Have your daughter's full name, dates of employment (October), and last known address ready. Sometimes W2s are returned due to address changes. 2. **Check for electronic delivery** - Many Taco Bell locations now use electronic W2 delivery through their employee portal. Ask the manager if they use Workday or another system where she might be able to access it online. 3. **Get the payroll company info** - If the store can't help immediately, ask who handles their payroll (often ADP, Paychex, or similar). You can contact them directly with her employee information. 4. **Document your attempts** - Keep records of when you called and who you spoke with. The IRS will ask for this if you need their help later. Since it's already past the January 31st deadline for employers to mail W2s, Taco Bell is technically non-compliant. If you don't get resolution within a week, call the IRS at 800-829-1040. They can issue a formal request to the employer, which usually gets quick results. Even for a small amount like $200, it's worth getting the actual W2 rather than estimating. Plus, if any taxes were withheld, she'll want that refund!