This is exactly the kind of confusion that trips up so many people! Based on everything you've described, it sounds like your employer is providing what's essentially a taxable health stipend but calling it an "HRA" - which is causing all the confusion. The fact that it's showing up in your regular paycheck and included in your W-2 taxable income is the dead giveaway. A legitimate HRA would be administered separately from payroll, require you to submit receipts for reimbursement, and wouldn't appear as taxable income on your W-2. Since you're remote and their regular plan doesn't work for your location, what they're doing makes sense from a practical standpoint - they're trying to help you out. But from a tax perspective, they've structured it as additional compensation rather than a qualified health benefit. I'd suggest having a conversation with HR to clarify whether they intended this to be a formal HRA (in which case they need to restructure it) or if they're comfortable with it being taxable supplemental pay to help with your healthcare costs. Either approach is fine, but the tax treatment should match the actual structure. Don't feel bad about being confused - the terminology around health benefits is genuinely confusing, and many employers use these terms loosely without understanding the specific legal requirements behind them.

Great question and you're definitely not an idiot! This is one of the most misunderstood areas of employee benefits. What you're describing sounds like a taxable health stipend rather than a true HRA. The key red flags are: - Money comes through regular payroll - Shows up as taxable income on your W-2 - No requirement to submit receipts or documentation A compliant HRA requires your employer to establish a formal written plan document, have you submit qualified medical expense receipts, and reimburse you outside of payroll (with no W-2 inclusion). Many well-intentioned employers call their health stipends "HRAs" without realizing there are strict IRS requirements. Your employer is trying to help, but they've structured it as taxable compensation. I'd recommend asking HR for: 1. The formal HRA plan document 2. Claims submission procedures 3. Confirmation of how reimbursements are processed If they can't provide these, then you'll know it's actually taxable income (which is fine, just different from what they're calling it). You might want to suggest they either properly structure an HRA or simply call it what it is - a health insurance stipend to help with your remote work situation.

Thanks for all the detailed responses everyone! This is exactly the kind of insight I was hoping for. Based on what I'm hearing, it sounds like H&R Block would be the better choice for my situation. The software-based training seems more practical, and the advancement opportunities are appealing since I'm thinking about this as a potential career path rather than just seasonal work. @Sofia Peña and @Luca Esposito - your points about the franchise vs corporate structure really resonated with me. I hadn't considered how much that could affect the quality and consistency of the experience. I think I'm going to finish out my current Liberty Tax class (since I'm already halfway through) but then switch to H&R Block for actual employment. At least the foundational knowledge from Liberty's manual approach might give me a solid understanding of the concepts, and then I can learn the practical software skills at Block. Has anyone made a similar switch mid-season or between companies? Any tips for making that transition smooth? Really appreciate everyone taking the time to share their experiences!

I've been working in tax preparation for about 5 years now and wanted to add a perspective on the client experience side of things. One major difference I've noticed is that H&R Block clients tend to have higher expectations for service quality, which can be both good and bad. Good because it pushes you to really know your stuff and provide thorough explanations. Bad because you'll deal with more demanding clients who expect perfection. Liberty Tax clients are often more focused on speed and getting their refund quickly, so there's less pressure for detailed explanations but more emphasis on volume and efficiency. From a learning standpoint, I'd echo what others have said about Block being better for career development. They also offer more specialized training - like workshops for small business returns, rental property, etc. - which can really boost your skills and earning potential. The other thing to consider is office culture. This varies by location, but in my experience, H&R Block offices tend to be more professional environments, while Liberty can be more casual (sometimes too casual). If you're looking at this as a serious career move, the professional atmosphere at Block might serve you better for networking and building relationships in the industry. Also worth noting - Block typically has better resources for handling audits and IRS correspondence, which is something you'll definitely encounter as you gain more experience with complex returns.

I made the mistake of not dealing with this properly at my first nanny job and it was a NIGHTMARE come tax time. If your employer won't do a W-2, you'll have to file as self-employed using Schedule C and Schedule SE, and you'll pay BOTH portions of Social Security/Medicare taxes (15.3% instead of 7.65%). Plus, quarterly estimated tax payments are your responsibility if you go the self-employed route. Don't ignore this! The penalties add up.

As someone who's worked in tax compliance for years, I want to emphasize that getting this right from the start is crucial. You're absolutely correct to be concerned about this - many people get into trouble by treating nanny work as casual income. The key point everyone's made about you being a household employee (not an independent contractor) is spot-on. Since you'll be earning $14,400-18,000 annually, this definitely triggers the household employer tax requirements. Here's what I'd suggest for your conversation with the family: Be upfront that you want to handle taxes properly and ask how they plan to manage payroll taxes. You can mention that household employees earning over $2,400 annually require proper tax withholding and a W-2. If they seem hesitant, explain that it protects both of you - you from tax penalties and them from potential liability for unpaid employment taxes. The IRS takes household employment taxes seriously, and the penalties can be substantial for both parties. Document everything - keep records of all Zelle payments, your work schedule, and any agreements. Even if they handle taxes properly, good records are essential for your own tax filing.

This is a frustrating situation that many field workers face. While the tax deduction landscape changed significantly in 2018, there are still some important distinctions to understand about your specific situation. Since you mentioned you don't have a regular office and travel to different client sites daily, this could potentially change how your mileage should be classified. The IRS distinguishes between: 1. **Commuting** - travel from home to your regular workplace (not deductible) 2. **Business travel** - travel between work locations or to temporary work sites (should be reimbursable) If you're truly going to different temporary work locations each day rather than one fixed workplace, your employer's policy of treating the first 90 miles as "commuting" may not align with IRS guidelines. Here's what I'd recommend: - Document that you have no fixed office location - Keep records showing you visit different client sites - Research IRS Publication 463 which covers travel expenses - Present this information to your employer's HR/finance department While you can't currently deduct unreimbursed employee expenses on your personal taxes, you may have grounds to argue for better reimbursement from your employer based on the temporary work location rules. The key is demonstrating that your daily travel pattern doesn't fit the traditional "home to office" commute model.

I've been following this thread and want to add something important that might help your case. The IRS actually has a specific ruling about workers who have no fixed office location - it's called the "home office deduction" principle, but it also applies to travel reimbursement policies. If your home is your principal place of business (which sounds like it might be, since you get assignments there and have no fixed office), then travel from your home to temporary work locations should be considered business travel, not commuting. This is covered under IRS Revenue Ruling 99-7. The key factors the IRS considers are: - Do you perform administrative tasks at home? - Do you receive work assignments at home? - Is your home where you store work materials/tools? - Do you have no other fixed business location? If you can answer "yes" to these questions, you have a strong argument that your employer's 90-mile "commute" exclusion is incorrect. Your home should be treated as your business headquarters, making all travel to client sites reimbursable business travel. I'd suggest documenting these factors and presenting them to your employer along with Revenue Ruling 99-7. Even though you can't deduct unreimbursed expenses personally, this ruling could help you get proper reimbursement from your company.

One thing no one has mentioned - if you're gambling on sites that aren't legal in the US, reporting those winnings doesn't make the gambling itself legal. You still have to pay taxes on illegal income (IRS doesn't care where money comes from, they just want their cut), but reporting it doesn't protect you from other legal issues related to using those platforms. Most people don't run into problems, but just something to be aware of since you mentioned the platform isn't regulated in the US.

Great question! I went through something similar last year with about $8K in crypto gambling profits. Here's what I learned after consulting with a tax professional: The key thing is that you need to report the fair market value in USD at the time you received each winning, not when you eventually cash out. So if you won 0.5 ETH when ETH was $2,000, that's $1,000 of taxable gambling income even if ETH later drops to $1,500. For your situation with $13.5K in profits, you'll report this as "Other Income" on Form 1040 Schedule 1. Since you haven't converted to USD yet, you're not dealing with capital gains/losses on the crypto holdings themselves - that only comes into play when you sell. One practical tip: start documenting everything now while it's still relatively fresh in your memory. Create a spreadsheet with dates, amounts won in crypto, and the USD value at that time. You can use sites like CoinGecko or CoinMarketCap to get historical pricing data. The IRS expects you to use "reasonable methods" to determine fair market value, so using widely-accepted pricing sources should be fine. Also remember that if you have gambling losses, you can potentially deduct them against your winnings if you itemize deductions, but only up to the amount of your winnings.