22 Has anyone tried using the IRS Tax Withholding Estimator for this situation? The website says it works for multiple jobs but I'm finding it confusing af to use...

Great discussion here! I went through this exact same situation about 6 months ago when I started my corporate job while keeping my weekend Instacart deliveries. One thing I learned the hard way - don't underestimate your gig income when using any of these tools. I was conservative with my estimates and ended up owing about $800 at tax time. It's definitely better to overestimate and get a small refund than to owe money. Also, keep really good records of your gig work throughout the year. I use a simple spreadsheet to track weekly earnings from each platform, plus all my expenses (gas, car maintenance, phone mount, etc.). Makes everything so much easier when tax time comes around. The quarterly payment thing mentioned earlier is super important too. I set up automatic reminders in my phone for the due dates so I don't forget. Missing those can result in penalties even if you end up getting a refund when you file your return.

You can also file a complaint with your state's labor board. Most states take this pretty seriously.

This is so frustrating! I went through something similar and here's what worked for me: First, send your employer a certified letter requesting your W-2 - this creates a paper trail. Then call the IRS at 800-829-1040 like others mentioned. While you wait, gather ALL your pay stubs from 2024 to calculate your total wages and withholdings. If you don't have them, check if your employer has an online portal where you can download them. The IRS can issue a CP2000 notice to employers who don't comply, and they face penalties of $50-$280 per missing W-2. Don't let them push you around - you have rights!

One option nobody's mentioned is using an Employee Stock Ownership Plan (ESOP) to facilitate the transfer. This could potentially allow your dad to defer capital gains taxes if structured properly.

Consider exploring a Section 1202 qualified small business stock (QSBS) analysis as well. If your S Corp qualifies and your father has held his shares for at least 5 years, he might be eligible for significant capital gains exclusion (up to $10 million or 10x basis, whichever is greater). Also worth discussing with your advisors is the timing of any conversion strategies. Some families benefit from converting to a C Corp temporarily before the sale to take advantage of QSBS benefits, then converting back afterward, though this requires careful planning around the built-in gains tax rules. Another angle to explore is whether your father might benefit from charitable remainder trust (CRT) strategies if he has philanthropic goals. This could allow him to defer capital gains while providing income over time and eventual charitable benefits. The key is running the numbers on multiple scenarios before committing to any single approach. Each family's situation is unique based on the business value, personal tax situations, and long-term goals.

y'all remember to check your transcripts at midnight EST if ur cycle 05. thats when they usually update

Cycle codes are pretty consistent! I've been cycle 05 for the past 3 years and it hasn't changed. Just make sure you file from the same address and use the same SSN format. The IRS assigns you to a processing center based on your location and that usually stays put unless you have major life changes like moving states or getting married/divorced.

I went through this exact drama with my daughter last year! She worked at the mall and filed her taxes, then my husband freaked out thinking we couldn't claim her anymore. We actually brought all our paperwork to a tax preparer who laughed and said this happens all the time. Bottom line: a dependent filing their own tax return has NOTHING to do with whether the parent can claim them. They're completely separate things. As long as you're under 19, live at home, and your mom provides more than half your support, she can absolutely claim you AND get the child tax credit. Show your mom this thread!

Your brother is definitely wrong, and you're absolutely right! This is one of the most common tax misconceptions out there. Filing your own tax return does NOT disqualify you from being claimed as a dependent - these are two completely separate things. Since you're a minor who worked and earned income, you're actually REQUIRED to file your own return if you made over the filing threshold (usually around $400 for self-employment income or $12,950 for regular wages in 2024). But this has zero impact on your dependency status. Your mom can still claim you as a dependent as long as you meet the basic tests: you're under 19, lived with her more than half the year, and she provided more than half of your financial support. She'll also still be eligible for the $2,000 Child Tax Credit since you're under 17. The only thing that matters is that you checked the box on YOUR return indicating that someone else can claim you as a dependent. If you did that correctly (which it sounds like you did), then there's absolutely no conflict. You can show your family IRS Publication 501 which clearly states this, or even call the IRS directly to confirm. Don't let them stress you out over this - you did everything right!