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Tony Brooks

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One thing nobody's mentioned yet - make sure you keep really good records of all your trades, not just rely on the 1099. Tradovate should give you detailed statements, but sometimes brokers make mistakes on the tax forms. I learned this the hard way last year when my 1099 had incorrect totals. Also, if you did any day trading of futures (opening and closing positions on the same day), the reporting gets a bit more complex and having your own records will help your tax preparer tremendously.

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Thanks for mentioning this. Do you recommend any specific way to track trades? Should I just export statements from Tradovate monthly or is there a better system?

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Tony Brooks

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I'd recommend exporting your statements at the end of each month at minimum. Personally, I use a simple spreadsheet where I record the date, contract, entry/exit prices, and P&L for each trade. This makes it much easier to verify the 1099 is correct when it arrives. There are also trading journal apps like TraderVue or TradeMetria that can import your Tradovate data and organize it nicely, which gives you both performance metrics and good tax records. Whatever system you choose, the important thing is consistency and making sure you capture all the necessary details.

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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.

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Are you sure about that? I thought Section 1256 contracts were totally exempt from wash sale rules regardless of contract size. My tax guy told me this was one of the main benefits of futures over stock trading.

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Mei Liu

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I'm so sorry for your loss, Natasha. Dealing with tax paperwork while grieving is never easy. The advice here is spot on - you'll sign YOUR name on the signature line, not your aunt's. Write "Personal Representative" in the occupation field, and make sure to write "DECEASED" with the date of death (November 2024) across the top of the form. Since you mentioned you weren't court-appointed but are handling her affairs as the only living relative, you should definitely include Form 56 with the return to notify the IRS of your fiduciary role. This protects you and establishes your authority to act on her behalf. For her final return, you'll report all income she received from January 1, 2024 through her date of death in November. The interest, pension, and Social Security income you mentioned will all go on the regular lines of Form 1040. If there's a refund due, you'll likely need Form 1310 to claim it since you're not a surviving spouse. Take your time with this - the IRS generally allows up to 3 years from the original due date to file a final return, so there's no need to rush and make mistakes. You're doing a loving thing by handling her final affairs properly.

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Liam Mendez

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This is really comprehensive advice, thank you Mei! I'm new to this community and dealing with my grandfather's final tax return. One thing I'm still confused about - if I need to file Form 1310 to get his refund, do I file that at the same time as the 1040, or do I wait until after the return is processed? Also, is there a specific deadline for filing the final return, or just the normal April 15th deadline that would have applied to him?

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Ethan Brown

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Hi Liam! You'll file Form 1310 at the same time as the 1040 - attach it to the tax return when you mail it in. Don't wait until after processing, as the IRS needs it to authorize releasing the refund to you as a non-spouse representative. For the deadline, the final return follows the same filing deadline that would have applied to your grandfather. So if he normally filed by April 15th, that's still the deadline for his final return (April 15, 2025 for the 2024 tax year). However, if you need more time, you can file for an extension using Form 4868, which gives you until October 15th to file the actual return. One important note - even though you have until the normal deadline to file, if there are any taxes owed, interest and penalties can still accrue from the original due date. So if you think taxes are owed, it's better to file sooner rather than later, or at least make an estimated payment by the April deadline. Hope this helps with your grandfather's return!

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I'm sorry for your loss, Natasha. Having handled my grandmother's final return last year, I understand how overwhelming this can feel when you're already dealing with grief. The key points others have covered are correct - you'll sign YOUR name on the signature line (not your aunt's), write "Personal Representative" in the occupation field, and mark "DECEASED" with her date of death at the top of the form. One thing I wish someone had told me earlier: keep detailed records of everything you do related to her estate, including copies of the tax return and any correspondence with the IRS. You might need these later for estate administration or if any questions come up. Also, since you mentioned she had Social Security income, be aware that if she received any Social Security payments after her date of death, those may need to be returned to the Social Security Administration. This is separate from the tax return but something to check on. The IRS has a helpful Publication 559 ("Survivors, Executors, and Administrators") that walks through all the requirements for filing a decedent's final return. It's available free on their website and really helped me understand the process when I was in your situation. You're doing the right thing by asking these questions and making sure everything is handled properly. Take it one step at a time.

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Sean Doyle

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Thank you for mentioning Publication 559 - that's such a valuable resource! I'm also dealing with a family member's final tax return and didn't know about this publication. Your point about Social Security payments received after death is really important too. I hadn't thought about that aspect. Do you know if there's a specific timeframe for returning those payments? And is it something the family needs to initiate, or does Social Security automatically detect it? Also, when you mention keeping detailed records for estate administration - are there any specific documents beyond the tax return copies that you found particularly important to keep? Sorry for all the questions, but this is all new to me and your experience sounds really helpful!

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Jenna Sloan

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Just to add some more confusion lol - make sure you're also reporting any dividends properly if your ESPP shares paid any. Those would be on a separate 1099-DIV typically. Nothing is ever simple with stock compensation!

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This! And also watch out for wash sales if you're buying similar company stock in other accounts around the same time as selling your ESPP shares. Tax software often misses these connections.

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This thread has been incredibly helpful! I'm dealing with a similar ESPP situation but have an additional wrinkle - my company was acquired mid-year and I had shares from both the old company's ESPP and received cash-out payments for unvested portions. The acquiring company's HR said the cash-out should be on my W2, but I'm not seeing it clearly separated. Has anyone dealt with ESPP complications during M&A? I'm worried I'm missing something important for my tax filing.

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Diego Flores

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M&A situations with ESPPs can be really tricky! The cash-out payment for unvested shares should definitely show up somewhere on your W2, but it might not be clearly labeled. Look for any unusual amounts in Box 1 (wages) or Box 14 (other compensation) that you can't account for. Sometimes companies put acquisition-related payouts in Box 14 with a code. You might also receive a separate 1099-MISC if the cash-out was handled by the acquiring company rather than your original employer. I'd recommend reaching out to both HR departments (old and new company) to get a clear breakdown of what's included where. The timing of the acquisition during the offering period could also affect how the discount is calculated and reported. Don't let this slip through the cracks - acquisition payouts often have different tax treatment than regular ESPP transactions!

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Oliver Weber

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I've been banking with US Bank for about 6 years and can confirm what others have said - they stick to the exact IRS date, no early releases. But here's something that might help with your planning: US Bank typically processes their ACH batches around 2-3 AM on the deposit date, so your refund will usually be available first thing in the morning rather than later in the day. Since you filed March 3rd and got accepted same day, you're actually in a pretty good spot timing-wise. Most people who filed early March are seeing deposit dates in the March 20-25 range right now. One thing I learned the hard way - don't schedule any automatic payments for the exact day you expect your refund. Give yourself at least a day buffer just in case there are any processing delays on either the IRS or bank side. Also, if you're really anxious about the timing, you can call US Bank customer service and ask if they see any pending Treasury deposits to your account. They can often see incoming ACH transfers a day or two before they post, which might give you that extra peace of mind for your planning.

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Noah Ali

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This is really great advice about the 2-3 AM processing time! I had no idea US Bank had such a specific schedule for ACH batches. That's actually perfect for my situation since I need to make a daycare payment first thing Monday morning - knowing the funds will be there early morning rather than sometime during the day makes a huge difference for my planning. I'm definitely going to follow your suggestion about not scheduling automatic payments for the exact deposit date. Better to be safe than sorry with overdraft fees! Thanks for the tip about calling customer service to check for pending Treasury deposits - that's something I never would have thought to ask about.

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Fiona Sand

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I work in banking operations (not at US Bank specifically, but familiar with ACH processing industry-wide) and wanted to add some technical context that might help you and others understand the timing better. US Bank, like most traditional banks, follows Federal Reserve ACH settlement schedules strictly. When the IRS sends your refund, it goes through the Fed's ACH network with a specific "effective date" - this is the earliest date the receiving bank is allowed to make those funds available to you. US Bank doesn't choose to hold funds longer than required, but they also don't release them early as a matter of policy. The reason some online banks can offer early access is they're essentially giving you a short-term advance against the incoming deposit - they're taking on risk to provide that service. Traditional banks like US Bank generally don't offer this. For your March 3rd filing date, you're looking at roughly 18-21 calendar days from acceptance for direct deposit, so your window is probably March 21-24 as others mentioned. The fact that WMR shows approved means you've cleared the main processing hurdles and are just waiting for the Treasury to schedule the payment batch. Pro tip: US Bank's online banking typically updates around midnight, so you might see the deposit reflected before you wake up on deposit day, which helps with early morning financial planning.

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Lim Wong

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Make sure you're setting aside money for taxes on your moonlighting income! This sounds obvious coming from a CPA but you'd be surprised how many tax professionals get this wrong. You'll likely need to make quarterly estimated payments unless you adjust your W-4 withholding at your day job. Also, track your time meticulously for billing and to justify deductions. I use toggl.com for easy time tracking between different clients.

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Dananyl Lear

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Been moonlighting for 2 years now and totally agree on the tax planning. Actually got hit with an underpayment penalty my first year cause I didn't make estimated payments. Rookie mistake from someone who should know better lol!

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Great question and congrats on the new baby! I started moonlighting about 2 years ago in a similar situation - corporate accounting role with a growing family needing extra income. A few things I learned the hard way: First, absolutely get your own E&O insurance before taking on any clients. Even if you think you're just doing "simple" returns, mistakes happen and the liability exposure is real. Second, be strategic about your client mix - I found that focusing on W-2 employees with maybe some investment income gives you predictable scope and timing. One thing that really helped me was being upfront with my day job employer early on. I scheduled a brief meeting with my manager and explained I was looking to do some part-time tax prep work that wouldn't compete with our business or interfere with my responsibilities. They appreciated the transparency and it actually opened up some conversations about potential advancement opportunities. The key is positioning it as professional development rather than just needing money. Frame it as staying current with individual tax law and building client service skills. Most employers understand that CPAs often do some side work, especially tax prep. Start small - maybe 3-5 clients your first year to see how you handle the workload during busy season. You can always scale up once you get a feel for the time commitment.

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Luca Russo

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This is really helpful advice, especially about framing it as professional development rather than just needing extra money. I hadn't thought about that approach but it makes so much sense from a career perspective. How did you handle the conversation with your manager? Did you give them specific details about what kind of tax work you planned to do, or did you keep it more general? I'm trying to figure out the right balance between being transparent and not over-sharing details they might not need to know. Also, when you say "start small with 3-5 clients," how did you find those first clients? I'm wondering if starting with friends/family is a good idea or if that creates more complications than it's worth.

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