Don't forget that if you trade micro e-minis or other small futures contracts, the wash sale rules don't apply like they do with stocks! This is a huge advantage for futures traders. You can take your losses in December to offset income and then jump right back into the same positions in January without triggering wash sale rules.

You're absolutely right to start gathering this information early! As someone who went through this same situation last year, here's what I wish I had known: Your tax preparer will definitely need the 1099 from Tradovate, but they'll also need to complete Form 6781 (Gains and Losses From Section 1256 Contracts and Straddles) to properly report your futures trading losses. The good news is that since you're using a professional tax preparer, they should handle all the form preparation - you just need to provide them with the documentation. Make sure to bring not just the 1099, but also any monthly statements from Tradovate showing your trading activity. Sometimes the 1099s can have errors, so having backup documentation is always smart. One advantage you have with futures losses is that they're marked-to-market at year-end, meaning any open positions are treated as if they were closed on December 31st. This can actually be beneficial for tax planning purposes. Since you mentioned you're new to filing with trading activity, I'd suggest having a brief conversation with your tax preparer about futures trading taxes before your appointment. Most good preparers are familiar with Section 1256 contracts, but it's worth confirming they have experience with trading taxes to avoid any surprises.

This is such a helpful thread! I'm in a similar situation where I might need to tap into my Roth IRA for an emergency expense, and I was completely unaware of the Form 8606 requirement. One thing I'm wondering about - if you've made contributions to multiple Roth IRAs (like I have one with Fidelity and another with Vanguard from a previous job), do you need to aggregate all your contributions across all accounts when calculating what you can withdraw tax-free? Or does each account get treated separately? Also, @Diego Mendoza, definitely check out that EAP suggestion! I used my company's emergency assistance program a few years ago and it was a lifesaver. Many people don't even know these programs exist. Sometimes they offer grants (not loans) for certain hardship situations, which would be even better than touching your retirement savings. Thanks everyone for sharing your experiences - this is exactly the kind of real-world advice you can't easily find elsewhere!

This is exactly the kind of situation I found myself in a couple years ago! You're absolutely right that Roth contribution withdrawals are tax-free and penalty-free since you already paid taxes on that money going in. Here's what you need to know: Yes, you do need to report the withdrawal on your tax return even though it won't be taxable. Your IRA custodian will send you Form 1099-R showing the distribution, and you'll need to file Form 8606 to prove to the IRS that you're only withdrawing contributions (not earnings). The 1099-R might look scary when you get it because it shows the full withdrawal amount, but don't panic - Form 8606 is where you do the math to show it's not taxable. Most tax software will walk you through this process by asking about your contribution history. Before you make the withdrawal, I'd strongly recommend gathering records of all your past Roth IRA contributions - check old tax returns for Form 5498 or your account statements. This will make the Form 8606 much easier to complete accurately. Also, when you request the withdrawal, be specific with your custodian that you want to withdraw "contributions only" to help ensure they process it correctly. One last thought - have you checked if your employer offers an Employee Assistance Program? Many companies have emergency loan programs that could help you avoid touching your retirement savings altogether. It's worth a quick call to HR first!

Does anyone know if my state taxes US obligation income differently than others? I'm in California if that matters. My tax software is asking about this but doesn't explain if California has special rules.

Just wanted to add something that might help clarify the confusion about finding this on your 1099 forms. When you're looking at your 1099-B, the "US obligations" won't necessarily be labeled that way explicitly. Look for securities with these types of identifiers or descriptions: - Anything starting with "912" (CUSIP numbers for Treasury securities) - Securities described as "T-BILL", "T-NOTE", "T-BOND" - "TREASURY" in the description - "UNITED STATES OF AMERICA" as the issuer Also, if you have a 1099-INT form, Box 3 will show "Interest on U.S. Savings Bonds and Treasury obligations" - this is separate from capital gains but shows if you held these types of securities during the year. Don't forget that if you sold Treasury securities at a loss, you still need to report them in this section (you'd enter a negative number for the loss). The state exemption applies to both gains and losses on these securities.

One thing nobody mentioned - if you're getting tax transcripts for a mortgage, make sure to ask your loan officer EXACTLY which transcripts they need! I got the wrong kind first (tax account transcript instead of tax return transcript) and it delayed my closing by a week. Some lenders also require the Record of Account transcript which is different. Save yourself time and get the right one first!

I went through this exact same situation last year when I lost all my tax documents in a basement flood. Here's what worked for me: First, definitely try logging into your old tax software accounts - TurboTax, H&R Block, FreeTaxUSA, etc. I was able to recover 3 years worth of returns this way even though I thought they were gone forever. For the IRS route, I'd recommend starting with the free transcripts online first since you need them quickly for your mortgage application. The Tax Return Transcript shows most of what lenders need, and you can get it instantly if you can verify your identity online. If that doesn't work, you can request them by mail using Form 4506-T (which is free, unlike the full return copies). One tip that saved me time - call your mortgage lender first and ask them exactly which years they need and what specific information they're looking for. Some lenders are fine with just the AGI and tax liability amounts, while others need more detailed breakdowns. This helped me avoid requesting more than I actually needed. Also, don't panic too much - this happens to more people than you'd think, and lenders are usually pretty understanding about the process taking a little time to get the documents together.

This whole discussion has been incredibly enlightening! As someone who's been renting for years and just started seriously house hunting, I had no idea about the complexity of itemized deductions vs. the standard deduction. One thing I'm wondering about as I look at potential homes - is there a way to estimate beforehand whether itemizing will be worth it for my situation? I'm looking at houses where the property taxes would be around $6-7K annually, and I live in a state with moderate income taxes (probably $4-5K withheld yearly). So I'd be right around that $10K SALT cap. With mortgage interest on top of that, it seems like I'd probably come out ahead itemizing, but I'm curious if there are any online calculators or rules of thumb for figuring this out during the home shopping process. It would be helpful to factor this into the overall cost analysis of different properties. Also, reading about all the document tracking and escrow timing complexities makes me realize I should probably start getting organized about tax record keeping well before I actually buy! Any suggestions for systems that work well for new homeowners?

This is such a valuable discussion for new homeowners! I went through this exact confusion when I first started itemizing after buying my house in 2022. The key insight that helped me was understanding that the SALT deduction isn't just about property taxes - it's about preventing the federal government from taxing you on money that's already been claimed by state and local governments. Your state income tax withholding represents money that never actually reached your pocket because your state government took it first. The federal system recognizes this by allowing you to deduct it. Think of it this way: if your gross pay was $50,000 but your state took $3,000 in income tax, you really only had $47,000 available to live on or pay federal taxes with. The SALT deduction ensures the federal government doesn't tax you on that full $50,000. One practical tip for tracking everything: I set up a simple Google Sheet with columns for date, amount, type (state income tax, property tax, charitable donation, etc.), and notes. Every time I get a relevant document - W2, 1098, property tax bill, donation receipt - I add it to the sheet immediately. Come tax time, I just sort by category and everything's ready to go. Much easier than digging through boxes of papers in April! The $10K cap is frustrating for those of us in higher-tax states, but at least understanding how it all works together helps with planning and peace of mind.