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Quick tip from a tax preparer: If you receive a 1099-K that includes personal transfers, make sure you keep a "contemporaneous log" of your business income. Basically, track tips as you receive them in a notebook or app - date, amount, and maybe client first name (for privacy). This real-time tracking is MUCH stronger evidence than trying to sort it out later. If you're ever audited, having records you created at the time of the transactions will be viewed much more favorably than a spreadsheet you made right before filing taxes.
For tracking tips and business transactions, I'd recommend something simple like a basic spreadsheet app (Google Sheets or Excel mobile) or even a dedicated expense tracking app like Mint or YNAB. The key is consistency - pick something you'll actually use every time you receive a payment. Some massage therapists I know just use their phone's built-in notes app but create a new note each month with a consistent format like "Date - Amount - Client Initials - Notes." Whatever you choose, just make sure you're recording it right when the transaction happens, not trying to remember later!
As someone who went through this exact situation last year, I can't stress enough how important it is to start organizing your records NOW rather than waiting until tax time. The 1099-K will show the gross amount, and you'll need to be able to justify which portions aren't taxable income. One thing I learned the hard way: Venmo's transaction descriptions can be super helpful for sorting business vs personal. Look for patterns - your massage clients probably use words like "tip," "service," or "massage" in their payment notes, while personal transactions might say things like "dinner," "rent," or just be emoji. Also, don't panic about hiring an accountant immediately. Try going through your transactions yourself first using the export feature, and if you get overwhelmed or your situation is more complex than expected, then consider professional help. Many tax preparers are familiar with this 1099-K mess now since it's affecting so many people. The key is documentation - keep everything showing how you determined what was business income versus personal transfers. Screenshots, spreadsheets, notes about regular clients, anything that shows your reasoning was legitimate and not just trying to avoid taxes.
Here's exactly what you need to do with your cycle code situation: 1. First, understand that 20250705 breaks down as: 2025 (IRS fiscal year) + 07 (7th week of processing) + 05 (Thursday processing day) 2. Next, check your account transcript for TC 846 code - this is your refund code 3. If you see TC 846, note the date next to it - that's your scheduled deposit date 4. If no TC 846 yet but you see TC 150 (return filed), you're in normal processing 5. Check again next Thursday morning as Thursday cycle codes typically update weekly Your W2 information is on a separate transcript and doesn't affect refund timing. With tuition due May 15th, you should have your refund well before then based on current processing times.
I understand your anxiety about the timing with tuition due May 15th! The good news is that cycle code 20250705 is actually a positive indicator - it means your return has been processed and assigned to the Thursday update cycle (that's what the "05" means). Since you filed March 1st and are seeing this update on April 12th, you're well within normal processing timeframes. The missing W2 information you mentioned is likely on your Wage & Income transcript rather than your Account transcript - these are separate documents that update at different times. I'd recommend checking your transcript again next Thursday morning, as that's when Thursday cycle codes typically get their next update. Based on the timing patterns others have shared here, you should definitely have your refund well before your May 15th tuition deadline. Hang in there!
This is really helpful information! I'm actually in a similar situation - filed early March and have been obsessively checking my transcripts. The explanation about W2 info being on a separate transcript makes so much sense now. I was getting worried because I kept seeing people mention codes that weren't showing up on my account transcript. Question though - when you say "Thursday cycle codes typically get their next update," does that mean every Thursday or just specific Thursdays? I'm trying to figure out if I should be checking weekly or if there's a different pattern.
One thing nobody's mentioned - if you carried back your 1256 losses, make sure you ALSO adjust your state tax return if your state bases income on your federal AGI. I forgot to do this and ended up getting a notice from my state tax authority about a discrepancy.
For anyone still struggling with 1256 contract loss carrybacks, I want to emphasize the importance of timing your election properly. You must make the section 1212(c) election by the due date (including extensions) of the return for the loss year - in your case, that would be the due date for your 2023 return. If you missed this deadline, you can't carry back the losses even if everything else is correct. This is a strict requirement that trips up a lot of people. The IRS won't accept a late carryback election even if you file an amended return later. Also, remember that you can only carry back losses to years where you had section 1256 contract gains OR other income. If 2022 was a loss year for you overall, the carryback might not provide any benefit and you'd be better off carrying the losses forward instead. Make sure to keep detailed records of all your SPX options trades, including the specific contract months and strike prices, as the IRS may request this information during their review process.
This timing detail is crucial - I almost missed this deadline myself! Just to clarify for anyone reading this, when you say "due date including extensions" for the 2023 return, that would be October 15, 2024 if you filed an extension, correct? Also, regarding keeping detailed records of SPX options trades - should we be documenting the specific expiration dates and whether they were calls or puts? I have everything in my brokerage statements but I'm wondering what level of detail the IRS typically wants to see if they audit a 1256 carryback claim.
One thing nobody mentioned - check box 12 on your W-2 for code DD. If you see that, it shows the total cost of your employer-sponsored health coverage. This includes BOTH what your employer paid AND what you paid. This amount is just informational and not taxable. Most people don't realize their employer often pays a lot more than they do for health insurance. My DD amount was like $18,500 even though I only contributed about $3,600 myself through payroll!
Wow, thanks for this tip! I just checked my W-2 and I do see code DD in box 12 with an amount of $14,320. I had no idea this was the total cost - that's way more than what comes out of my paycheck each month. So just to be 100% clear, I don't need to report anything about my health insurance premiums anywhere on my tax return then?
Exactly! If you're like most employees with employer-sponsored health insurance where your portion is deducted pre-tax, you don't need to report anything about these premiums on your tax return. The DD amount is purely informational so you can see the total value of your health benefits. It's actually a good thing to check because many people don't realize how valuable their total compensation package is when you include these benefits. The $14,320 shown in your DD box is essentially additional compensation that you're not being taxed on!
Don't forget that if you're self-employed (which doesn't sound like your case, but for others reading), health insurance premiums ARE deductible as an adjustment to income (above-the-line deduction). I'm a freelancer and deduct 100% of my premiums without having to itemize. It's one of the few perks of self-employment lol.
Does this apply to dental and vision too? I'm also self-employed and have been paying for separate dental insurance but wasn't sure if I could deduct it along with my health insurance.
Yes! As a self-employed person, you can absolutely deduct dental and vision insurance premiums along with your health insurance premiums. They all qualify for the self-employed health insurance deduction on Schedule 1 of Form 1040. Just make sure the insurance policies are in your name (or your spouse's/dependents' names) and that you're not eligible for coverage through a spouse's employer plan. It's a great above-the-line deduction that reduces your adjusted gross income.
Santiago Martinez
OP, I think you need to check if your tax software correctly classified your Traditional IRA contribution as non-deductible. At your income level with a workplace plan, you're definitely above the deduction phaseout limits. What should happen is: 1. Your capital loss of $3k reduces your taxable income by $3k 2. Your Traditional IRA contribution should be classified as non-deductible 3. You should file Form 8606 to track your non-deductible contributions The $700 reduction in tax due is roughly consistent with just the $3k capital loss deduction at your tax bracket. You're probably not getting any deduction for the IRA contribution, which is correct based on your income.
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Jacob Lee
β’Thanks for the detailed explanation! That makes sense now - I didn't realize the Traditional IRA deduction phases out at my income level since I have a workplace retirement plan. I checked and my tax software did correctly mark it as non-deductible, which explains why I only saw the benefit from the capital losses. Would you recommend I do a Backdoor Roth IRA instead for this year? I've heard about it but wasn't sure if it applied to my situation.
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Santiago Martinez
β’Yes, the Backdoor Roth IRA would be perfect for your situation. Since you can't deduct traditional IRA contributions anyway, you might as well get the tax-free growth benefit of a Roth. The process involves making a non-deductible traditional IRA contribution (which you've already done) and then converting it to a Roth IRA. If you don't have any other traditional IRA assets, this is very clean tax-wise. Just be sure to file Form 8606 properly to document the non-deductible contribution, and then report the conversion on next year's taxes. The conversion itself isn't taxable if you convert soon after contributing (before significant gains occur).
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Samantha Johnson
Has anyone used the "What-If" scenario feature in tax software to see how different retirement contributions affect your tax outcome? I always run these before finalizing my return.
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Samantha Johnson
β’That's good to know! I need to use those tools more effectively. I think a lot of people (including me) just assume traditional retirement contributions always lower current taxes, without realizing the phaseout limitations. Did you find the what-if calculators accurate compared to your actual filing results?
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Samantha Howard
β’The what-if calculators in most tax software are pretty accurate for basic scenarios, but they sometimes miss the nuanced stuff like IRA deduction phaseouts. I've found they're great for comparing traditional vs Roth contributions when you're clearly above or below income limits, but they can be misleading in those gray areas where phaseouts apply. For someone like the OP with high income and workplace retirement plans, I'd recommend running the scenarios but also double-checking the results against IRS Publication 590-A to make sure the software is applying the phaseout rules correctly. Sometimes the calculators assume full deductibility when you're actually in a phaseout range.
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