This is a really common situation and you're smart to catch it now! With your combined income of $85,000 ($42k + $28k + $15k), you're definitely going to be underwithheld since each employer is treating their portion as if it's your only income. Here's what I'd recommend: Focus on your highest-paying job ($42k) for the adjustment. Use the IRS withholding calculator or add extra withholding on line 4(c) of that W-4. A rough estimate would be to withhold an additional $150-200 per paycheck from that job to cover the shortfall. The key issue is that your $15k weekend job is probably being withheld at around 12%, but when combined with your other income, those dollars are actually being taxed at 22%. That gap across all your jobs is what's creating the problem. Don't wait - the sooner you adjust, the less you'll need to withhold per paycheck to catch up by year-end. If you're already past mid-year, you might need to withhold even more per check or consider quarterly estimated payments as someone else mentioned.

One thing I'd add that hasn't been mentioned much - make sure you're also considering state taxes in your calculations! I made the mistake of only focusing on federal withholding when I had multiple jobs last year and got hit with a surprise state tax bill too. Each state employer was also treating their portion as my only income for state withholding purposes. In my case (California), the state tax brackets made this an even bigger issue than the federal shortfall. If you're using any of the tools mentioned here like the IRS calculator or taxr.ai, make sure they're accounting for your state taxes too. Some states have much steeper progressive tax rates than others, so the underwithholding problem can be amplified at the state level. Also, with your weekend gig bringing in $15k, double-check that your employer is actually withholding taxes from those paychecks. Some smaller employers or gig work might be treating you as a contractor (1099) rather than an employee (W-2), which would mean no withholding at all and you'd need to make estimated payments for that income.

9 To add something practical - if you do decide to issue a corrected 1099, you don't need to file a new 1096. You would just submit the corrected 1099 marked as "CORRECTED" and the IRS will match it to your original submission. You can order more 1099 forms online from the IRS website or get them at office supply stores. But honestly, for just an address change, I wouldn't bother with a correction. The TIN matching is what matters for tax compliance.

As someone who's been handling 1099s for contractors for over a decade, I can confirm what others have said - address errors alone don't require corrected filings with the IRS. The matching system relies on TIN and income amounts, not mailing addresses. However, I'd suggest a middle-ground approach: reach out to your contractor and explain that while the IRS doesn't require a correction for address-only changes, you're happy to issue a corrected form if they have a specific business need for it (like mortgage applications or business loan requirements). This shows good customer service while also educating them about the actual tax implications. For your internal processes, definitely update their address in your system now so next year's forms are correct. And keep a record of their request - it shows you're maintaining good documentation practices even when corrections aren't legally required.

Don't forget to also look into how this might affect financial aid! When my kid got a tuition benefit from my university job, it counted as a resource in financial aid calculations and reduced her eligibility for other university scholarships and grants. In our case, the tuition benefit wasn't taxable, but it did mean she couldn't get need-based aid from the university that she might have otherwise qualified for. We ended up slightly better off financially, but not as much as we initially thought. Also, if your daughter is applying early decision, make absolutely sure you understand how the benefit works beforehand. Once you commit through early decision, you're obligated to attend regardless of the financial package.

As someone who went through this exact situation three years ago, I can confirm that the Section 117(d) qualified tuition reduction for undergraduate education is indeed tax-free with no dollar limit. My daughter's tuition was around $75K and we didn't pay a penny in taxes on that benefit. The key thing that helped me was getting everything in writing from HR before my daughter committed. I asked specifically for documentation that confirmed our benefit was structured as a "qualified tuition reduction under IRC Section 117(d)" rather than taxable compensation. This documentation was crucial when I filed our taxes - my tax preparer needed it to properly exclude the benefit from our income. One tip: ask your HR department for the specific tax code they use when reporting (or not reporting) this benefit. If they're treating it correctly as a Section 117(d) benefit, they shouldn't be issuing you any tax forms for it at all. If they mention Forms 1098-T or W-2 reporting, that might indicate they're treating it as taxable income, which would be wrong for undergraduate tuition benefits for employees' dependents. The early decision timeline does add pressure, but getting this clarity upfront will give you peace of mind. In my experience, most university HR departments understand these rules well once you use the specific tax code language - it's just that they're cautious about giving tax advice.

after 5 months of my transcript being blank and the as of date changing multiple times, i finally broke down and spent money on claimyr.com to actually talk to a human at the IRS. turns out they flagged my return because my 2022 return hadn't fully processed yet due to a clerical error on their end. the agent fixed it right away and I got both refunds within 2 weeks. sometimes you just need to talk to a real person to fix these issues.

I'm going through almost the exact same thing! Filed in March 2023 and my transcript has been blank forever. Just like you, I've had to verify my identity multiple times (twice online and once by phone). My "as of" date also recently changed to a future date in 2025. It's so frustrating because you feel completely in the dark about what's happening. I've been checking my transcript obsessively too, hoping to see some kind of update or code that would give me a clue about the status. From what I'm reading in the other comments, it sounds like the date change might actually be a positive sign that things are moving forward. I really hope that's the case for both of us! Let me know if you see any other updates on your transcript.

Speaking from experience (3 years running a US-based online marketing business while traveling), the technical/practical aspects were actually harder than the legal/tax aspects. Time zone challenges when clients expect meetings during US business hours but you're in Asia was brutal. Internet reliability is another huge factor - I learned to always have backup internet options (local SIM with hotspot capability + regular wifi). Also recommend setting up a good VoIP phone service that lets you maintain a US number. I use Google Voice which lets me make/receive US calls from anywhere. Clients never knew I was responding from a beach in Bali at 11pm my time.

One thing I haven't seen mentioned yet is visa requirements and how they might affect your tax situation. While you can absolutely run your US business from abroad, some countries have strict rules about working on tourist visas, even if it's remote work for a US company. Countries like Thailand, Vietnam, and several European nations are cracking down on "digital nomads" working on tourist visas. Getting caught could result in deportation and future visa denials. Consider looking into digital nomad visas that several countries now offer - Portugal, Estonia, and Barbados have legitimate remote work visas. Also, be aware that spending too much time in certain countries (usually 183+ days) can trigger tax residency there, which could complicate your US tax situation even with the FEIE. Each country has different thresholds and rules. I'd strongly recommend consulting with both a US international tax attorney AND researching the work visa requirements for each country you plan to visit. The $500-1000 you spend on proper legal advice upfront could save you from major legal and tax headaches down the road.