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I had a friend who didn't report about $1200 in side income from these apps. The IRS sent him a letter 18 months later asking about it! Turns out the person who paid him filed it as a business expense, which created a mismatch. Not worth the stress IMO.
Thats scary. Did ur friend have to pay penalties or just the taxes they should have paid originally?
He had to pay the back taxes plus interest, but luckily no penalties since it was considered an honest mistake rather than intentional tax evasion. The IRS was pretty reasonable about it once he explained the situation and paid what he owed. Still, the whole process took months to resolve and was super stressful. Better to just report everything upfront!
Thanks for asking this question - I was wondering the same thing! Based on all the responses here, it's clear that even small amounts like your $650 need to be reported. I appreciate everyone sharing their experiences with the various tools and services mentioned. One thing I'd add is to make sure you keep good records of what the payments were for. If it was truly income from work/services, you'll need to report it. But if any of those CashApp payments were reimbursements from friends (like splitting dinner bills) or gifts, those might not be taxable income. The key is being able to document the nature of each payment. It sounds like the safest approach is to report everything and let the IRS sort it out rather than risk getting a letter later asking questions you can't easily answer.
Great point about distinguishing between actual income and reimbursements/gifts! That's something I hadn't considered before. I've been treating all my CashApp transactions the same way, but you're right that splitting a restaurant bill with friends isn't taxable income. Do you happen to know if there's a specific way the IRS expects us to document the difference? Like if I received $100 from a friend but $50 was reimbursement for concert tickets I bought for both of us and $50 was payment for helping them move, would I need some kind of written record of what each payment was for? This whole thread has been super helpful - definitely better to be overly cautious than deal with IRS letters later!
Has anyone tried the W-2 import feature in TurboTax for a situation like this? I'm curious if it would pull in both W-2s or just one, and if it would handle the differences automatically.
I used TurboTax's import feature in a similar situation last year. In my case, it only imported the Federal/State W-2 and I had to manually enter the local tax information separately. The software prompted me specifically for city taxes in a different section, so it worked out fine in the end.
I just went through this exact situation last month! When you have two W-2s like this from the same employer, it's usually because of a mid-year change in tax jurisdictions (which matches your husband's office move). Here's what worked for me: Use the Federal/State W-2 as your primary form in TurboTax. This has all your complete federal wage and tax information. The City/Local W-2 is supplementary and should only be used for the local tax sections. For Box 12 specifically, the differences you're seeing make sense: - The lower Code C amount ($390 vs $1,350) on the City/Local form reflects the reduced life insurance benefit calculation after the move - The Code D difference ($10,900 vs $11,800) shows 401k contributions were slightly different between the two periods - Code AA only appears on the Federal/State form because that's where the complete annual Roth 401k contribution total is reported TurboTax's import feature will likely only grab the Federal/State W-2, so you'll need to manually enter the city tax amounts in the local tax section. Don't worry about "double reporting" - the software keeps federal and local separate. Just make sure you're using the right form for each section!
Bit of a tangent, but what gambling log app do people recommend? I've been using a paper notebook which is getting unwieldy. Is there a good mobile app that lets you log sessions and wins/losses on the go?
I've been using "Gambling Log Pro" for a couple years and it's pretty decent. It's like $4.99 on the app store but worth it. You can enter sessions real-time, take photos of tickets/W-2Gs, and it calculates daily and yearly totals. It also exports to PDF for tax time.
This is exactly why I always recommend keeping contemporaneous notes while gambling! The key thing to remember is that your gambling log should reflect the actual time you were gambling, not when the casino's "gaming day" officially ends. Here's what I do: I note the actual calendar date and time when I start and stop gambling, regardless of what the casino considers their "gaming day." If I'm playing at 2am on February 15th, that's what goes in my log as February 15th activity. When I get a W-2G that shows February 14th for that same jackpot, I make a note in my log like "W-2G dated 2/14 due to casino gaming day policy" next to the February 15th entry. This creates a clear audit trail. The IRS has been pretty consistent that they want to see gambling activity tracked by actual calendar days, not casino accounting periods. Your approach of wanting to stay organized by calendar days is correct - just make sure you have those reconciliation notes to explain any date discrepancies on your tax forms.
This is really helpful advice! I've been struggling with the same issue and wasn't sure how detailed those reconciliation notes needed to be. When you write "W-2G dated 2/14 due to casino gaming day policy" - do you also include the W-2G form number or any other identifying information in that note? I want to make sure I'm creating a strong enough paper trail in case of an audit. Also, do you keep a separate master list that shows all your W-2G forms and their corresponding actual gambling dates, or do you just rely on the individual notes in your daily log entries?
As someone who's been through this exact same situation, I can confirm what everyone else is saying - TurboTax handles everything automatically once the IRS releases your refund. The timing is really consistent too. I've used the refund deduction option for the past 3 years and it's always been 1-2 business days from when WMR shows "sent" to when the net amount (after TurboTax fees) appears in my account. Since your expected date is April 3rd and the kids' activities don't start until April 5th, you'll have a comfortable buffer. One thing I'd suggest is setting up account alerts with your bank so you get notified immediately when the deposit hits - that way you can finalize any last-minute planning for those spring activities without stress!
This is exactly what I needed to hear! Setting up bank alerts is such a smart idea - I'm definitely doing that today. It's amazing how much peace of mind everyone's responses have given me. As a first-time TurboTax user, I was really stressed about not knowing when exactly the fees would come out and whether I'd have enough time to get everything sorted for the kids' activities. Knowing that 1-2 business days is the standard timeline and that it's all automatic makes this so much less overwhelming. Thank you for sharing your multi-year experience - it really helps to hear from someone who's been through this process multiple times!
Just wanted to add another perspective as someone who's used TurboTax's refund deduction option multiple times! The process really is as straightforward as everyone's describing. One thing that might help with your peace of mind - you can actually log into your TurboTax account and see a detailed breakdown of exactly what fees will be deducted before they take them out. This helped me budget precisely when I was in a similar situation with tight timing for family expenses. Also, most banks process ACH deposits overnight, so if WMR shows your refund as "sent" on April 3rd (which is a Thursday), there's a good chance you'll see the money (minus TurboTax fees) in your account by Friday morning April 4th, giving you a full day buffer before the kids' activities start. The automatic nature of the whole process is actually a relief once you get used to it - no action needed on your part at all!
This is incredibly helpful, especially the tip about being able to see the fee breakdown in advance! I just logged into my TurboTax account and found exactly what you're talking about - it shows I'll be charged $89.99 total ($49.99 federal + $39.99 state + refund processing fee). Knowing the exact amount ahead of time makes budgeting so much easier. The Friday morning deposit possibility is even better than I hoped for - that would give me the whole weekend to get everything organized for Monday's activities. It's such a relief to know this is all automated and I don't have to worry about missing some step or deadline. Thanks for taking the time to share these details!
Dmitri Volkov
I went through this exact same confusion last year! The key thing that helped me understand it was thinking about it from the IRS perspective - they want to see the full economic activity of your business, not just what hits your bank account after third parties take their cuts. So yes, report the gross amount customers pay as income, then deduct PayPal fees as a business expense. This is actually beneficial for you because it gives you a larger deduction and more accurately reflects your business activity. One practical tip: PayPal's monthly statements make this pretty easy to track. They show both your gross sales and total fees for each month, so you don't have to calculate transaction by transaction. I just download the monthly summaries and use those numbers for my tax prep. Also worth noting - if you're using PayPal Goods & Services, those fees are definitely deductible business expenses. But if you ever use Friends & Family for business (which you shouldn't), those transactions get murkier from a tax perspective since that's technically not a business payment method.
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Kelsey Hawkins
ā¢This is super helpful, thanks! I'm just starting my business and had no idea about the Friends & Family thing being problematic for business use. I almost set that up to avoid fees - glad I didn't! One quick question - when you say download the monthly summaries, do you mean the actual PayPal statements or is there a specific report I should be looking for? I want to make sure I'm getting the right documentation for my records.
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Mei Wong
ā¢You'll want to look for the "Monthly Financial Summary" that Liam mentioned earlier in the thread - it's under your PayPal Business account reports section. This breaks down your total payments received, fees charged, and net deposits for each month. You can also download your full transaction history as a CSV file which gives you line-by-line detail of every transaction and fee. For tax purposes, either works, but the monthly summary is cleaner if you just need the totals for your Schedule C. And yes, definitely avoid Friends & Family for business! The IRS expects business transactions to go through proper merchant services, plus you lose buyer/seller protections. Always use Goods & Services even though the fees are higher - those fees are tax deductible anyway, so it's not as painful as it seems.
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Diego Chavez
Great question! I had the same confusion when I started my business. You definitely want to report the FULL amount customers pay as income and deduct the PayPal fees separately as business expenses on Schedule C. Here's why this matters: If you only report the net amount, you're essentially letting PayPal reduce your income without getting the tax benefit of those fees as deductions. By reporting gross income and deducting fees, you get the full business expense deduction you're entitled to. Also, keep in mind that if you receive a 1099-K from PayPal (which reports the gross amounts to the IRS), your tax return needs to match what they've already told the IRS you received. If you only report the net amounts, there will be a discrepancy that could trigger questions. The fees typically go under "Commissions and fees" or "Payment processing fees" on your Schedule C. Make sure to keep good records - I save my PayPal monthly statements which clearly show both gross receipts and total fees charged. This makes tax prep much easier and gives you solid documentation if the IRS ever has questions. One last tip: set up a separate PayPal account just for business if you haven't already. Mixing personal and business transactions makes everything more complicated come tax time!
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Philip Cowan
ā¢This is exactly the kind of clear explanation I needed! I've been stressing about this for weeks. Just to make sure I understand correctly - if a customer pays me $500 and PayPal takes $15.20 in fees, I report $500 as income and $15.20 as a business expense, right? And this way I'm still paying tax on $484.80 of actual income but I get the proper deduction? Also, when you mention keeping PayPal monthly statements, do you print them out or just save the PDFs? I'm trying to figure out the best way to organize all this paperwork for my records.
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