I'm confused about what specific job expenses we're talking about. Does this include things like home office supplies if we're working remote? Or uniforms? What about professional licenses and continuing education?

I'm a CPA and wanted to clarify something important that might help with your $850 in unreimbursed expenses. While you're correct that most unreimbursed employee business expenses aren't deductible as itemized deductions from 2018-2025, there are still some options to explore. First, double-check if any of your expenses fall into categories that ARE still deductible - like educator expenses (if you're a teacher), certain moving expenses (for military), or impairment-related work expenses. Second, consider asking your employer about implementing an accountable plan as others mentioned. This is honestly your best bet for getting tax-free reimbursement going forward. Third, if any of your expenses relate to education or training that maintains or improves job skills, you might qualify for education tax credits instead of deductions - these can actually be more valuable than deductions anyway. Finally, keep detailed records of everything. If the TCJA provisions aren't extended past 2025, you'll want that documentation ready for potential future deductions. The political landscape around tax policy is always changing, so staying organized pays off long-term.

Have you checked if you made any payments to them via PayPal, Venmo, or any other payment apps? Sometimes you can find their info that way. Also check any invoices or emails they might have sent you. There's often contact info in email signatures or invoice headers.

I went through something very similar with a freelance graphic designer last year - paid them $1,800 and then they completely vanished when I needed their W-9 for tax filing. Here's what I learned from the experience: 1. File the 1099-NEC anyway with "UNKNOWN" in the address field and blank TIN/SSN as others mentioned. The IRS prefers incomplete filing over no filing. 2. Document EVERYTHING - save screenshots of any old emails, text messages, or calls you made trying to reach them. This becomes crucial if you need to request penalty abatement later. 3. Check your bank records for any additional contact info. Sometimes contractors include business names or phone numbers in payment descriptions that might help you track them down. 4. The $280 penalty isn't automatic - you can request reasonable cause relief when you receive the notice. I successfully got mine waived by showing I made good faith efforts to obtain the information. 5. For the contractor's side - they're still legally required to report that income even without receiving a 1099. The IRS has ways of matching unreported income, so this will likely catch up with them eventually. Don't panic too much - this happens more often than you'd think with small businesses. Just make sure to implement the W-9 requirement before payment going forward!

This is exactly the situation I found myself in last year! The 400% FPL cliff is brutal when you're self-employed because income can be so unpredictable. One thing that helped me was making a last-minute SEP-IRA contribution before the tax deadline. Since you can contribute up to 25% of your net self-employment income (or about 20% of your Schedule C profit after the SE tax deduction), this can significantly reduce your MAGI. I was able to contribute about $15,000 which brought me well under the 400% threshold. Also, don't forget about the SE tax deduction itself - half of your self-employment tax reduces your MAGI for PTC purposes. And if you have a spouse, you might want to run the numbers on married filing separately vs. jointly, as this can sometimes help with PTC optimization. The key is to think holistically about all your above-the-line deductions, not just the health insurance piece. Sometimes it's better to maximize retirement contributions and take a smaller health insurance deduction rather than the other way around.

This is such a well-documented example of why the ACA's subsidy structure can be so punitive for self-employed individuals. You're absolutely correct that strategically limiting your SE health insurance deduction to stay under 400% FPL is often the optimal approach, even though it feels counterintuitive. One additional consideration I'd mention: if you're planning ahead for next year, you might want to look into income smoothing strategies. Since you know about this cliff now, you could potentially time certain business expenses or income recognition to avoid getting caught at the threshold again. Also, keep detailed records of your actual health insurance premiums paid versus what you deduct. The IRS has been increasing scrutiny on SE health insurance deductions, and having clear documentation of why you chose a specific deduction amount (PTC optimization) rather than the full premium amount can be helpful if questioned. The fact that a $100 difference in deduction can result in an $8,800 swing in tax liability really highlights how broken this particular part of the tax code is. You're making the right financial choice, even if the system seems designed to trip people up.

I've been through this exact situation and wanted to share what really helped me get through it without the stress and uncertainty that I see you're experiencing. When I made the same Head of Household vs Single mistake on my W4, I was panicking about how much I might owe and whether I was calculating everything correctly. After spending way too much time trying to figure out the math myself, I decided to use a professional tax analysis service. I ended up using TaxAct's withholding analysis tool, which connected me with a tax professional who reviewed my paystubs and calculated exactly how much I was underwithholding each pay period. They also helped me determine the right amount to add on line 4(c) of my corrected W4 to catch up over the remaining months. What I really appreciated was having an expert walk me through the numbers instead of trying to guess based on online calculators. The peace of mind was worth every penny - I knew exactly where I stood and had a clear plan to fix it. Plus, they helped me understand the safe harbor rules so I knew I wouldn't face any penalties. The whole process took about 30 minutes, and I walked away feeling completely confident about my tax situation instead of constantly worrying about it. Sometimes it's worth investing in professional guidance when you want to make sure you're handling something correctly the first time.

I made this exact same mistake when I started my current job last year! The feeling of panic when you first realize it is totally normal, but I can assure you this is much more manageable than it seems. Here's what I learned: at your income level ($65k), you're probably looking at roughly $35-45 less being withheld per paycheck. Since you caught this in April, you've likely had maybe $300-500 total underwithholding so far - definitely not the thousands you might be imagining. My recommendation is to take a two-step approach: 1. Get a new W4 to HR this week with the correct Single filing status 2. Use the IRS withholding calculator to determine if you need extra withholding on line 4(c) to catch up The beauty of catching this now is that you have 8+ months to correct course. When I was in your shoes, I added about $50 extra per paycheck on line 4(c) and ended up getting a small refund instead of owing money. Don't let the anxiety eat at you - this happens to more people than you'd think, and your HR department has seen it countless times. They'll process the correction without any drama. You're being responsible by addressing it promptly, and that's exactly the right approach!

As a newcomer to this community, I've been following this discussion with great interest since I'm facing the exact same decision! This thread has been incredibly enlightening - it's clear that the choice really comes down to personal preferences and specific needs rather than one version being objectively superior. What I find most helpful is how everyone emphasized that both versions will calculate your taxes correctly using the same engine. I've been getting caught up in comparing every little feature when what really matters is choosing the approach that fits my comfort level and workflow. Based on all the experiences shared here, I'm leaning heavily toward TurboTax Online for my first serious comparison. The automatic document imports, live chat support with screen sharing, and device flexibility all sound like they'd significantly reduce the stress I typically feel during tax season. The fact that it's more forgiving for beginners is exactly what I need right now. The advice about trying the free version first is brilliant - I can actually experience the interface rather than trying to predict what I'll prefer. Sometimes analysis paralysis is worse than just picking a reasonable option and moving forward! Thank you all for creating such a valuable resource. This peer-to-peer advice based on real experiences is far more useful than any comparison chart I've found online. It's refreshing to see a community where people take the time to share practical insights that genuinely help newcomers navigate these decisions.

As another newcomer to this community, I've been reading through this entire discussion with fascination! It's incredible how what started as a simple question about TurboTax versions turned into such a comprehensive resource for people facing this decision. What really stands out to me is how consistently everyone emphasized that both versions will produce the same accurate tax results - it's really just about your preferred way of working. I think I was getting too caught up in trying to find the "objectively best" option when it's more about finding what works best for my specific situation and comfort level. The consensus around TurboTax Online being more beginner-friendly really resonates with me. The live chat support with screen sharing, automatic document imports, and device flexibility all sound like they'd make tax season significantly less stressful. Plus, the ability to easily get help when I inevitably have questions seems invaluable. I'm definitely going to take the advice about trying the free version first - it makes so much more sense to experience the interface rather than trying to imagine it from descriptions. And knowing I can always switch to Desktop next year if I want more control takes the pressure off making the "perfect" choice right now. Thank you all for sharing such detailed, practical experiences. This kind of peer advice from people who've actually been through this decision is exactly what I needed to stop overthinking and just move forward!