@Abigail Patel - I was in a similar situation when I started with gig work! Here's what I wish someone had told me right away: Since you're earning around $800 so far and expect to make $2500-3000 total, you'll definitely need to pay self-employment tax (15.3%) plus regular income tax. The good news is you have some time before the September 15th deadline. My advice: Start tracking your mileage RIGHT NOW if you haven't already. Every mile you drive while working (including driving to your first delivery and between orders) is deductible at $0.67 per mile. This can significantly reduce what you owe. For a rough estimate, take your gross earnings, subtract your mileage deduction, then set aside about 25-30% of what's left for taxes. You can use Form 1040-ES to calculate your exact quarterly payment. Don't stress too much - as a new gig worker, there are safe harbor rules that can help you avoid penalties even if you underpay slightly. The most important thing is to start tracking everything now and make your best estimate for the September payment. Also keep receipts for any work-related expenses like phone bills, hot bags, car maintenance, etc. - these are all deductible!

@Abigail Patel - Since you're just starting out with Doordash, here's a simple action plan for your situation: **Immediate steps:** 1. Download a mileage tracking app TODAY (Stride is free and works great) 2. Start tracking every mile while you're dashing - this will be your biggest tax deduction 3. Set aside 25-30% of your earnings in a separate savings account for taxes **For the September 15th deadline:** Since you've only made $800 so far, you likely won't owe a huge amount for this quarter. You can use the IRS Form 1040-ES worksheet to calculate your exact payment, but don't panic if you can't pay the full amount - there are penalty safe harbors for new self-employed workers. **Key deductions to track:** - Mileage (67¢ per mile in 2024) - Phone bill percentage used for work - Any supplies like hot bags, phone mounts, etc. **The 1099 situation:** You're right that Doordash will send you a 1099-NEC if you earn over $600, but it won't come until January 2025. Don't wait for it - you need to track your own earnings and make quarterly payments based on what you know you've earned. Since this is your first year, focus on getting into good tracking habits now rather than stressing about perfect calculations. The most important thing is starting that paper trail!

This is such a helpful thread! I'm also a veteran dealing with the same HSA eligibility questions. One thing I wanted to add that might help others - if you're unsure about whether your VA appointments count as service-connected or not, you can actually request a detailed breakdown from the VA. I called and asked for a summary of my benefits usage that specifically categorizes each appointment/service by whether it was for a service-connected disability or general VA healthcare. This documentation was crucial when my employer's HSA administrator questioned my eligibility. Also, for those considering the financial trade-offs that PrinceJoe mentioned - don't forget that HSA funds can be used for dental and vision expenses too, which often aren't fully covered by VA benefits. Plus things like over-the-counter medications, medical equipment, and even some alternative treatments can be HSA-eligible expenses. The deadline pressure is real, but it's better to take the time to get it right than to deal with IRS penalties later. Good luck with your decision!

This thread has been incredibly helpful! As another veteran navigating this same situation, I wanted to share a resource that helped me understand the complexities: the IRS Publication 969 specifically addresses HSAs and has a section on "Other Health Coverage" that details how VA benefits interact with HSA eligibility. One thing I learned that wasn't mentioned yet - if you have a spouse or dependents, their use of VA benefits (like CHAMPVA) can also affect your HSA eligibility in some cases. The "other coverage" rules can get tricky when you have family members with their own VA-related benefits. Also, regarding the testing period rule that StarSeeker mentioned - this is HUGE and often overlooked. I almost got caught by this when I had an unexpected VA appointment in December that would have triggered the penalty for the entire year's contributions. For those still on the fence about the financial benefits: remember that unused HSA funds roll over indefinitely (unlike FSAs), and after age 65, you can use them for any purpose without penalty. It's essentially a stealth retirement account with better tax treatment than a 401k if used for medical expenses. Given your tight deadline, I'd recommend calling your employer's benefits line AND the HSA administrator (if they're different companies) to confirm exactly what documentation they'll need. Some require the VA paperwork upfront, others are more flexible. Don't let the deadline pass while waiting for perfect clarity - you can always adjust contributions later if needed.

This is such a helpful thread! I've been dealing with the same confusion about meals vs entertainment deductions for my freelance consulting business. One thing I learned from my tax preparer last year is to also keep notes about the business purpose and topics discussed during each meal - not just the receipt. The IRS wants to see that there was a legitimate business discussion, so I now keep a simple log on my phone noting who I met with, what business matters we discussed, and any follow-up actions. For example, instead of just keeping a receipt that says "Dinner at Mario's - $85", I'll note "Dinner with potential client Sarah Johnson to discuss Q2 marketing strategy for her startup. Discussed budget parameters and timeline. Follow-up: send proposal by Friday." This documentation has been invaluable when my accountant prepares my Schedule C, and it gives me confidence that I can substantiate these deductions if ever questioned. The business purpose requirement is just as important as getting the meal vs entertainment categorization right!

As someone who's been through multiple IRS audits for my small business, I can't stress enough how important proper documentation is for meal deductions. The IRS absolutely will scrutinize these expenses during an audit. Here's what I've learned works best for staying compliant: 1. **The "contemporaneous" rule**: Document the business purpose immediately, not weeks later when you're doing your taxes. The IRS considers notes made at or near the time of the expense much more credible. 2. **The 50% rule has exceptions**: Some business meals can actually be 100% deductible in specific situations (like meals provided to employees for the employer's convenience, or certain travel meals). Don't assume everything is automatically 50%. 3. **"Directly related" vs "associated" test**: For any borderline cases, ask yourself - was business the primary purpose of the expense, or was it primarily social with some business discussion? This distinction matters for deductibility. For your $7,200 in expenses, I'd recommend going through each receipt and applying the IRS's own tests. When in doubt, err on the side of caution - it's better to miss out on some deductions than to face penalties and interest later. The documentation standards are strict, but they're there to protect legitimate business expenses from being disallowed.

The babysitter is 100% trying to avoid paying taxes. I used to babysit and nanny through college and definitely didn't report anything because it was all cash. BUT if someone had asked for my SSN for their taxes, I would've given it because that's fair - they're entitled to their credit. Just make sure you have her LEGAL first and last name and correct address. The IRS will almost certainly follow up with her, not you. When I filed with a missing provider tax ID, I got my full credit and never heard anything about it. My guess is they went after the provider instead.

I went through this exact situation two years ago with my daycare provider. Here's what worked for me: 1. Send one final formal request via text AND email (if you have it) specifically stating: "I need your SSN or EIN to complete Form 2441 for the Child and Dependent Care Credit on my tax return. This is required by the IRS for the $3,100 I paid you for childcare services in 2024." 2. When she doesn't respond, file your return anyway. Complete Form 2441 with her full legal name and address, leave the SSN field blank, and attach a statement explaining your reasonable efforts to obtain the information. 3. Your statement should include: dates you requested the SSN, method of contact (texts/calls), copies of your payment records (Zelle transactions), and mention that she provides childcare services to multiple families. The IRS accepted my claim without any issues. They likely flagged her for not reporting the income rather than penalizing me for missing information I genuinely tried to obtain. You've done nothing wrong by claiming a legitimate tax credit you're entitled to. Don't let her tax evasion cost you $650!

16 Does anyone know if I'm supposed to report my student loan payments anywhere on the tax return? I took out loans to pay the tuition that's shown on my 1098-T.

Just want to add something important that hasn't been mentioned yet - if your scholarships/grants exceed your qualified tuition and fees, the excess amount might be taxable income that you need to report on your tax return. In your case, you have $12,372.25 in qualified expenses and $8,670.50 in scholarships, so you're fine. But if it were the other way around, that excess would generally need to be reported as income on Line 1 of your 1040. Also, make sure you understand the difference between "qualified expenses" for tax purposes versus what your school considers qualified expenses. For education credits, qualified expenses are generally limited to tuition, required fees, and required course materials - things like room and board typically don't count even if they're part of your school bill. This is definitely one of those areas where it's worth double-checking everything or getting professional help if you're unsure, since mistakes can trigger IRS notices later.