As someone who just went through this exact situation last year, I can confirm that FreeTaxUSA handles 1099 income really well. The key thing to remember is that you're looking for the "Self-Employment Income" or "1099-NEC" section under Income, not the old 1099-MISC section. Even if you never receive the official 1099-NEC form from your client, you absolutely must report that $4,875. Keep records of all payments - bank deposits, PayPal transfers, checks, whatever you have. The IRS cares about the income you earned, not whether you got the paperwork. One thing that caught me off guard my first year: make sure you understand that you'll owe self-employment tax (about 15.3%) on top of regular income tax. FreeTaxUSA calculates this automatically, but it can be a shock if you're not expecting it. For next year, consider making quarterly estimated payments to avoid a big tax bill. Also, start tracking every business expense now! Software subscriptions, art supplies, computer equipment, even a portion of your phone bill if you use it for work calls. These deductions can really add up for graphic designers.

Just wanted to share my experience since I went through this exact same confusion last year! The terminology around W9 vs 1099 forms trips up so many new freelancers. Here's the simple breakdown: You filled out a W9 FOR the company (giving them your tax info), and they should send YOU a 1099-NEC showing what they paid you. If they're calling what they gave you a "W9 with earnings," they're probably just confused about the terminology too. In FreeTaxUSA, go to Income → Self-Employment/1099-NEC and enter your $4,875 there. The system will automatically calculate your self-employment tax (which is about 15.3% on top of regular income tax - this was the biggest surprise for me!). Don't panic about not having the official 1099-NEC form yet. You're legally required to report that income whether you get the form or not. Just keep good records of all payments you received. Pro tip: Start a simple spreadsheet now to track every payment and business expense for next year. As a graphic designer, you can probably deduct software subscriptions, computer equipment, art supplies, and even part of your home internet if you work from home. These deductions saved me hundreds of dollars! The self-employment tax hit is real though - definitely start setting aside 25-30% of future freelance income for taxes. You might also want to look into quarterly estimated payments if you plan to keep freelancing.

I just want to echo what others have said - that CPA's advice is seriously concerning and could get you into real trouble with the IRS. The fundamental principle is that ALL income is taxable when received, regardless of whether you get a 1099 or any other tax document. The $600 threshold people keep mentioning is purely about *reporting requirements* for the companies paying you - it has absolutely nothing to do with whether that income is taxable to you. Even if you earned $1 from AdSense, it's technically taxable income that should be reported. For your specific situations, the referral bonuses from Rakuten and Chase are definitely taxable since you're essentially being compensated for marketing services. The AdSense income, even under $600, needs to be reported as self-employment income on Schedule C. The credit card welcome bonus is the only one that might not be taxable, and only if it was structured as a spending rebate rather than just a signup bonus. I'd strongly recommend getting a second opinion from a different CPA, because following the advice you received could result in significant penalties and interest if the IRS ever discovers the unreported income. The risk just isn't worth it, especially when the amounts you're talking about wouldn't result in huge tax bills anyway.

I want to add some perspective as someone who went through an IRS audit last year. While everyone here is absolutely correct that all income is technically taxable regardless of 1099s, I learned firsthand how these situations actually play out in practice. During my audit (which was triggered by a completely unrelated issue with my business expenses), the IRS agent specifically asked about "other income sources" and requested bank statements. They found several unreported items including PayPal payments, cash app transfers, and yes - credit card referral bonuses that I had forgotten about. Even though these were relatively small amounts ($300-800 each), I ended up paying penalties and interest that totaled more than the original tax owed. The agent explained that once you're in an audit, they look at EVERYTHING with a fine-tooth comb. Those small unreported income streams that seem insignificant suddenly become evidence of a pattern of non-compliance. What started as a simple business expense question turned into a much larger issue because of unreported income. My advice: report everything, even the small stuff. The tax you'll pay on these amounts is minimal compared to the potential consequences if you're ever audited. And definitely find a new CPA - the advice you received could seriously damage your relationship with the IRS if you follow it.

This thread has been incredibly helpful! I just want to add one more practical tip for anyone using TurboTax specifically. When you're entering the accrued market discount as interest income, make sure to enter it in the "Other Interest Income" section rather than trying to add it to any existing 1099-INT entries you might have. In TurboTax, go to Federal Taxes > Wages & Income > Interest and Dividends, then scroll down to the "Other Interest Income" section. Enter the $437 (or whatever your amount is) there and label it clearly as "Accrued Market Discount - T-Bill" in the description field. This keeps it separate from your regular interest income and makes it easier to track if you ever need to reference it later. The investment sales portion (for the proceeds and cost basis from your 1099B) should be entered separately in the Investment Income section under "Stocks, Mutual Funds, Bonds, Other." TurboTax will automatically calculate any capital gain/loss from that information. I learned this the hard way after initially trying to modify my 1099-INT entries and creating a mess that took forever to untangle. Keeping the market discount separate as "other interest income" is definitely the cleaner approach!

Thank you all for this incredibly detailed discussion! As someone who's been hesitant to trade T-Bills because of the tax complexity, this thread has been a goldmine of practical information. I especially appreciate how you've covered everything from the basic tax treatment (market discount as interest income on Schedule B) to the more advanced strategies like the de minimis election and constant yield method. The step-by-step TurboTax instructions are particularly valuable. One thing I'm curious about - for those of you who are actively trading T-Bills, do you find it's still worth it after factoring in all this additional tax complexity? I'm wondering if the potential returns justify the extra record-keeping and form preparation time, especially for smaller position sizes. Also, has anyone run into issues during an IRS audit related to T-Bill market discount reporting? I'm always nervous about these more complex tax situations and whether having all the right documentation would be sufficient if questions ever came up.

Great detective work everyone! This is exactly the kind of real-world payroll scenario that trips people up. Dylan's case is a perfect example of why it's so important to look at ALL compensation, not just your regular salary. For anyone else dealing with confusing YTD calculations, here are the key things to check: 1. **All forms of compensation** - bonuses, commissions, overtime, reimbursements that might be taxable 2. **Gross-ups** - when companies pay extra to cover the tax burden on bonuses or benefits 3. **Pay period vs. pay date** - YTD is typically based on when money was earned, not when the check was cut 4. **Mid-year benefit changes** - 401k enrollments, insurance changes, etc. can affect different YTD categories differently 5. **System errors** - unfortunately, payroll software glitches do happen The fact that Dylan's numbers worked out to exactly 5 paycheck equivalents was the smoking gun that there was additional compensation beyond the 4 regular paychecks. Always look for that kind of mathematical precision when troubleshooting YTD discrepancies!

This is such a helpful thread! I work in HR and see this confusion about YTD calculations all the time. Dylan's situation is actually really common - the gross-up on sign-on bonuses catches a lot of people off guard because they don't realize the company is essentially paying extra to cover the tax impact. One thing I'd add to the great advice here: if you're ever unsure about your YTD calculations, don't hesitate to reach out to your HR or payroll department early in the year. It's much easier to catch and correct discrepancies when there are fewer pay periods to review rather than waiting until you're halfway through the year. Also, keep all your paystubs! Even in this digital age, I recommend downloading PDFs or keeping physical copies. You'd be surprised how often employees need to reference old paystubs for things like loan applications, tax preparation, or resolving payroll discrepancies months later. Great job everyone helping Dylan solve this puzzle - this is exactly the kind of collaborative problem-solving that makes these forums so valuable!

I've been in a similar situation with multiple jobs and want to emphasize something important that hasn't been mentioned yet - make sure you're tracking your income throughout the year, especially with those variable bartending shifts. Since you mentioned you might only work the restaurant 1-2 times per month for around $150 per shift, that could still add up to $1,800-3,600 annually depending on tips. The unpredictable nature of service industry income makes it tricky for any withholding calculator. My recommendation would be to take a middle-ground approach: Use your full-time job's W-4 to handle the heavy lifting by checking the multiple jobs box and adding about $35 per paycheck on line 4c. This should cover your base tax liability from all sources. Then, set aside about 20-25% of your bartending earnings in a separate savings account as you go. If you end up owing a little at tax time, you'll have that cushion. If you don't need it, great - you've got some extra savings! This strategy has saved me from both overwithholding stress and tax-time surprises. Also consider doing a mid-year check-in around July to see how your actual income is tracking against your estimates. You can always submit a new W-4 to adjust if needed.

Just want to add another perspective here - I'm a tax preparer and see this exact situation all the time. Your income level of around $40k puts you in the 12% tax bracket, but the tricky part with multiple jobs is that each employer withholds as if that's your only income, which usually results in underwithholding. For your specific situation, I'd recommend using the IRS Tax Withholding Estimator first to get a baseline, then add a small buffer since your bartending income is unpredictable. The conservative approach others mentioned (adding $35-40 extra on your full-time job's W-4) is solid advice. One thing to keep in mind - if you do end up owing more than $1,000 when you file, you could face underpayment penalties even if you get a refund from overwithholding at one job. The IRS wants to see steady payments throughout the year, not a big catch-up at filing time. Also, don't forget that your bartending tips should be reported as income too. Many people overlook this, but cash tips count toward your total tax liability. Since you mentioned $22/hr plus tips, those tips could add a significant amount to your annual income depending on the restaurant's volume. Better to slightly overwithhold and get a refund than deal with penalties and a big tax bill next spring!