I really appreciate everyone sharing their experiences - this has been incredibly helpful! I was feeling pretty overwhelmed about this whole situation, but seeing that others have successfully navigated similar circumstances gives me confidence. I think I'm going to start with the gentle conversation approach that several people mentioned. Framing it as "I need proper documentation for my taxes" seems like a good way to bring it up without being confrontational. If my boss is willing to switch to proper business payments going forward, that would make everything cleaner. But if not, at least I'll know where we stand. In the meantime, I'm definitely going to implement the record-keeping suggestions - screenshots of all Venmo payments, detailed spreadsheet with dates/amounts/work descriptions, and saving all my supply receipts. The 25-30% savings rule for taxes is something I'm starting immediately. I've been living paycheck to paycheck partly because I wasn't setting aside anything for taxes, which was obviously not smart. One follow-up question - for those who filed Schedule C in similar situations, did you face any issues or additional scrutiny from the IRS? I'm still a bit nervous about reporting income that doesn't have official 1099 documentation, even though I know it's the right thing to do. Thanks again for all the practical advice - this community has been a lifesaver!

I completely understand your situation and the stress you're feeling! The good news is that many people have successfully handled this exact scenario. Since your employer is paying through Venmo "friends and family," you're essentially being treated as an independent contractor, which means you'll report this income on Schedule C (Profit or Loss from Business) along with your Form 1040. The IRS doesn't care how you were paid - income is income and must be reported. Here's what you need to do: 1. Keep detailed records of every payment (screenshots, dates, amounts) 2. Document the work performed for each payment 3. Save receipts for all work-related expenses (supplies, transportation, equipment) 4. Set aside 25-30% of each payment for taxes since you'll owe both regular income tax and self-employment tax (15.3%) You might consider having a respectful conversation with your boss about switching to proper business payments by simply saying "I need proper documentation for my taxes." Some employers don't realize the implications and are willing to change. The most important thing is protecting yourself by reporting the income correctly, regardless of what your employer does. You've got this!

Giovanni, you're absolutely right to feel confused - this is honestly one of the most common questions from people getting their first "real" job with benefits! The difference between your Box 3 and total gross income is completely normal and actually shows that your benefits package is working in your favor. Here's what's happening: Your total gross income (shown in that Earnings Summary section) includes every single dollar you earned before any deductions. Box 3 (Social Security wages) shows what's left after certain pre-tax deductions are subtracted - things like health insurance premiums, 401(k) contributions, HSA contributions, dental/vision coverage, and other pre-tax benefits. The simple formula is: Total Gross Income - Pre-tax Deductions = Box 3 This difference is actually saving you money! Those pre-tax deductions mean you're paying Social Security taxes (6.2%) on a smaller amount while still getting the full benefit of your gross earnings. It's one of the key advantages of having good benefits. To verify everything is calculated correctly and put your mind at ease, grab your final December pay stub and look for "Social Security wages" in the year-to-date column - it should match your Box 3 exactly. If those numbers align (which they should), then your employer did everything right and you can stop worrying about potential errors. Welcome to the world of employee benefits - once you understand how these numbers work together, you'll really appreciate how much these pre-tax deductions are helping your overall financial picture!

Giovanni, you're definitely not overthinking this - your confusion is completely understandable and shared by pretty much everyone who gets their first W2 with benefits! Here's the simple explanation: Your total gross income (what you see in the Earnings Summary) is literally every dollar you earned throughout the year before ANY deductions. Box 3 (Social Security wages) is what remains after certain pre-tax deductions are removed - things like health insurance premiums, 401(k) contributions, HSA contributions, and other pre-tax benefits your employer offers. Think of it as: Total Gross Income - Pre-tax Deductions = Box 3 (Social Security wages) This difference is actually working in your favor! Those pre-tax deductions reduce the amount you pay Social Security taxes on (which saves you 6.2% on those dollars) while you still get the full value of your gross earnings through benefits and take-home pay. To double-check that everything was calculated correctly, grab your final pay stub from December and look for "Social Security wages" in the year-to-date section - it should match your Box 3 exactly. If it does, then your employer processed everything properly and you can relax! This is actually one of the great advantages of having a job with good benefits - you get tax savings that add up to real money while building your health coverage and retirement savings. Welcome to the world of employee benefits!

Does anyone know if you can claim the American Opportunity Tax Credit for previous years when filing late? I think that might help reduce what OP owes since it's worth up to $2,500 per year if you qualify.

I work at a tax preparation office and want to add a few important points that might help you feel less overwhelmed about this situation. First, the IRS has programs specifically for situations like yours. You may qualify for an "Offer in Compromise" if your financial situation makes it difficult to pay the full amount owed. As a college student with limited income and assets, this could significantly reduce what you owe. Also, don't forget about the Lifetime Learning Credit in addition to the American Opportunity Tax Credit mentioned earlier. If you've exhausted your 4 years of AOTC eligibility or don't qualify for it in certain years, the LLC can provide up to $2,000 per year in tax credits for qualified education expenses. One strategy that might help: since you mentioned having only $4,000 available, you could file all your returns first to see exactly what you owe after credits and deductions. The actual amount might be much lower than you think, especially with education credits. Then you can set up an installment agreement with the IRS for as little as $25-50 per month while you're still in school. The key is to file those returns as soon as possible to stop the failure-to-file penalties from continuing to accrue. The IRS is generally very understanding with students who made honest mistakes about scholarship taxation rules.

I've been handling trust returns for my elderly father's trust for the past three years and wanted to add another perspective. Since you mentioned being comfortable with TurboTax for personal returns, you might want to consider UltimateTax - it's designed for tax professionals but has a really intuitive interface that bridges the gap between consumer software and professional-grade tools. What I like about UltimateTax is that it costs around $200 for their package that includes 1041 filings, but it comes with unlimited e-filing and phone support during tax season. The support team actually knows trust taxation, which was huge for me when I had questions about depreciation on rental property held in the trust. The software does a great job explaining the "why" behind trust-specific calculations, especially around the compressed tax brackets that trusts face. It also has built-in warnings if you're missing common deductions or making errors that could trigger IRS scrutiny. One feature that really helped me was their document checklist - it tells you exactly what financial documents you need before starting, which prevents the stop-and-start process that can make trust filing feel overwhelming. They also provide sample completed returns so you can see what a properly filed trust return should look like.

Based on your situation, I'd strongly recommend starting with FreeTaxUSA's premium version that Madison mentioned - at $25 for trust returns, it's an incredibly low-risk way to test the waters. Since you're already comfortable with consumer tax software from your personal returns, this would be the most natural transition. If you find FreeTaxUSA too basic for your trust's needs, then consider stepping up to UltimateTax ($200) which Aurora described as having that sweet spot between consumer-friendly interface and professional-grade capabilities. The phone support with people who actually understand trust taxation could be invaluable for a first-time trust filer. I'd avoid the expensive professional software like Lacerte unless your trust has unusual complexity - sounds like overkill for your situation. And while the AI-powered solutions like taxr.ai are intriguing, I'd personally want to stick with more established software for something as important as trust tax filing. One additional tip: since your aunt's previous tax preparer retired, see if they kept copies of the last few years of trust returns. Having those as reference documents will help immensely regardless of which software you choose - you can see exactly how similar transactions were handled in the past.

I'm so sorry you're going through this ID.me nightmare! I had a similar issue earlier this year and it was absolutely maddening. Here's what I learned from my experience: The "I don't have access to my phone" option that several people mentioned is definitely your best first step - it's hidden in tiny text at the bottom of the login page, but it actually works. When I used it, I had to upload a clear photo of my driver's license and it took about 5 business days to get approved (a bit longer than some others experienced, but still way better than phone support). One tip that saved me: when uploading your ID photo, make sure you're in really bright, even lighting and the entire ID is perfectly flat and in focus. They rejected my first attempt because apparently one corner of my license was slightly shadowed. Also, use a plain background - I put my ID on a white piece of paper. While you're waiting for that to process, definitely submit Form 4506-T as your backup plan. It's free and you can mail it or fax it to the IRS directly. Takes longer (10-15 business days for me), but at least you know you'll get your transcript eventually. The whole ID.me system is such a mess - you'd think they'd have better processes for legitimate account holders who just changed phone numbers. It's a super common situation! Hopefully one of these options gets you sorted out quickly.

This ID.me situation is absolutely infuriating! I went through something very similar about 6 months ago when I had to change my phone number due to harassment calls. The system is definitely broken when legitimate taxpayers can't access their own information. Here's my experience: I tried the phone support route first (complete waste of time - 2+ hour holds just to get disconnected), then discovered the "I don't have access to my phone" link that others have mentioned. It's ridiculously small text at the bottom of the login page, but it does work. For the photo submission, I learned this the hard way: take the photo during daytime near a window for natural light, put your ID on a white sheet of paper, and make sure your phone camera is directly above the ID (not at an angle). My first two attempts got rejected for "poor image quality" until I figured out their very specific requirements. The whole process took about 4 business days for approval, which honestly felt like a miracle compared to their phone support disaster. I also submitted Form 4506-T the same day as backup insurance, which ended up arriving in the mail right around the same time my ID.me access got restored. It's ridiculous that we have to jump through so many hoops to access our own tax records, but at least there are workarounds that actually function. Hang in there - you'll get through this mess!