I'm in a very similar situation and want to share what I learned from my CPA this year. I coordinate our neighborhood's annual block party and collected about $6,800 through Venmo from 40+ households for vendors, permits, entertainment, etc. I was terrified about the 1099-K implications. My CPA explained that the key is treating this properly as a "custodial" situation - you're essentially holding and disbursing funds on behalf of others, not earning income. She had me create a simple reconciliation showing: 1. Total collected via Venmo: $6,800 2. Total paid out for block party expenses: $6,750 3. My net: $50 (which I kept to cover my gas/time organizing) Only that $50 was reportable as income on my return. The rest was clearly documented as pass-through funds with receipts for every vendor payment, permit fee, etc. What gave me confidence was her explanation that the IRS sees tons of these community organizer situations - HOA treasurers, sports team parents, event coordinators. They understand the difference between someone running a business versus someone facilitating group payments. The documentation approach others mentioned here is spot on - keep those receipts showing money going back out, save Venmo screenshots with clear notes, and maintain a simple ledger. It's actually more straightforward than I initially thought once you frame it correctly as custodial funds rather than income.

Reading through everyone's experiences here has been incredibly helpful! I've been dealing with similar anxiety about Venmo reporting, but from a slightly different angle - I frequently use Venmo to split large purchases for my extended family gatherings. Throughout the year, I'll buy groceries, decorations, and supplies for family events (think Thanksgiving dinner for 20 people, birthday parties, etc.) and then have relatives Venmo me their portion. It probably totals around $4,000 annually, but it's clearly just cost-sharing for family events, not any kind of business income. What I'm taking away from this discussion is that I need to be much more diligent about documentation - keeping receipts for the original purchases, encouraging family members to use descriptive Venmo notes like "Thanksgiving dinner - my share," and maybe creating a simple spreadsheet tracking each event and who contributed what. It's such a relief to understand that the IRS recognizes these everyday money-sharing scenarios and isn't expecting every dollar on a 1099-K to be reported as income. The key seems to be honest reporting of actual taxable income combined with good recordkeeping to support your position if questions ever arise. Thanks to everyone who shared their experiences and practical advice - this thread should be required reading for anyone stressed about the new Venmo reporting requirements!

13 I'm a tax preparer and I see this ALL THE TIME. Usually it comes down to these factors: 1) Different assumptions about standard vs itemized deductions 2) Property tax entries not matching 3) State-specific credits being calculated differently 4) Different handling of retirement contributions 5) Health insurance premium tax credits

This is such a helpful thread! I'm dealing with the same issue right now - H&R Block is showing me a $400 higher refund than TaxSlayer and I couldn't figure out why. After reading through all these comments, I'm definitely going to double-check my property tax entries and state credit calculations in both programs. The suggestion about using taxr.ai to compare line-by-line is really appealing since I don't want to spend hours manually going through every field. And honestly, the Claimyr service sounds like it could save me a lot of frustration if I still can't figure out the discrepancy after checking everything myself. Thanks everyone for sharing your experiences - it's reassuring to know this is a common issue and not just me doing something wrong!

I went through the Jackson Hewitt refund advance process last year and this year, so I can share some perspective on what to expect! The timeline is usually pretty consistent - you should hear back within 24-48 hours like others mentioned, but I've found it's often closer to the 48-hour mark during busy tax season. One thing I learned is that they typically send the initial approval notification via text first, then follow up with email details. Make sure to check both! Last year I was refreshing my email constantly and almost missed the text. The approval amount varies but in my experience has been between 70-85% of your expected refund amount. They're pretty conservative to protect themselves, which makes sense. Once approved, the prepaid card setup is straightforward and you can start using it same day. Just hang tight Ruby - the waiting is stressful but Jackson Hewitt has been reliable in my experience. If you don't hear anything by tomorrow afternoon, definitely call their customer service line to check on the status. They're usually pretty helpful about giving you an update on where things stand.

I just went through the Jackson Hewitt refund advance process this past week and wanted to share my timeline to help anyone else waiting! Applied on Monday afternoon, got my approval text Wednesday evening around 6 PM - so right around that 48-hour mark everyone's been mentioning. The whole experience was pretty smooth once I got the approval. They sent me a link to activate the prepaid card online, which took maybe 5 minutes, and the funds were available within an hour. The card works just like a regular debit card and I was able to use it for purchases and ATM withdrawals right away. One tip I'd add is to make sure you have all your ID and banking documents ready when you apply - they verify everything during the appointment process and having it all organized seemed to help things move faster. Also, like others mentioned, definitely download their app to track your application status instead of just waiting around anxiously! The advance amount they approved was about 75% of my expected refund, which seemed fair given the circumstances. Overall, Jackson Hewitt's process was much more straightforward than I expected. Hope this helps anyone else going through the waiting period!

Just to add another wrinkle - are you sure your FSA isn't already a "limited purpose" FSA? Some employers offer these specifically for people with HSAs. If it is, then you CAN contribute to both at the same time because a limited purpose FSA only covers dental and vision. Check your benefits documentation carefully. Sometimes these are called "LPFSA" or might be automatically converted to limited purpose if you enroll in an HDHP.

One thing to keep in mind is that even though you have to wait until January to start HSA contributions, you can still maximize your HSA for 2025. The annual contribution limit for 2025 is $4,300 for individual coverage or $8,550 for family coverage, and you can contribute the full amount as long as you're HSA-eligible on December 1st of the tax year (this is called the "last month rule"). So even though you're missing out on October, November, and December 2024 contributions, you won't lose out on the full 2025 contribution opportunity. Just make sure to use up that remaining $1,100 in your FSA before the end of the year - stock up on eligible medical supplies, prescription medications, or even things like contact lenses and reading glasses if your plan allows it. Also, double-check if your FSA has a grace period that extends into 2025. Some plans give you until March 15th to use the previous year's funds, which would extend your HSA ineligibility period even further. Better to know now than be surprised later!

This thread has been incredibly helpful! I'm also self-employed with COBRA coverage and was making this way more complicated than it needed to be. Just to summarize what I'm understanding from everyone's advice: - My COBRA coverage gets reported on 1095-B (which I don't even need to file) - As self-employed, I should use the self-employed health insurance deduction on Schedule 1, Line 17 - This is much better than trying to itemize medical expenses since there's no 7.5% threshold - The deduction is limited to my self-employment profit One thing I'm still unclear on - do I need to wait for my 1095-B to arrive before I can file, or can I go ahead and file my return with just my COBRA payment records? My insurance company is always slow sending these forms out.

I went through this exact same confusion last year! As a fellow self-employed person with COBRA, I can confirm what everyone else is saying - you want the self-employed health insurance deduction, not the itemized medical expenses route. The key thing that helped me understand this: the 1095-B from your COBRA coverage is just proof you had insurance. You don't submit it with your taxes. What matters for the deduction is how much YOU paid in premiums (not what your former employer contributed). In TurboTax, I found the self-employed health insurance section under "Business Income and Expenses" then "Business Expenses." It asks for the total amount you paid for health insurance premiums during the year. Just enter your total COBRA payments and you're done. One heads up - make sure you calculate this correctly if you had any employment income during the year too. The deduction can get limited if you were eligible for employer coverage during part of the year, but since you mentioned you've been contracting all year, you should be fine to deduct the full amount (up to your self-employment profit). Good luck with your return!