I think you're right. I got a big promotion last year and our withholding never got adjusted. Is there a specific amount I should put for additional withholding on the W-4? And will I get penalized for having paid so little throughout the year?

You should use the IRS Tax Withholding Estimator on their website to calculate the exact amount for additional withholding. With your income level, you might consider putting an additional $500-700 per paycheck depending on your pay frequency. You might face an underpayment penalty if you didn't pay at least 90% of your tax liability during the year or 100% of last year's tax (110% if your income was over $150,000). The penalty isn't usually huge, but it's better to avoid it by making an estimated tax payment now if you can. You can make an estimated payment for 2025 using Form 1040-ES to help reduce any potential penalties.

I used H&R Block online and it was pretty straightforward. There's a specific section for unemployment compensation where you enter the 1099-G info. Make sure you're looking at box 1 on the form for the total unemployment amount and box 4 for any federal withholding.

I actually am taking some community college classes! Would that qualify me for education credits even though my income is low? Also, what's the income range for that Earned Income Tax Credit thing you mentioned? This makes me think I definitely should file even though the tax place told me not to.

Yes, education expenses could qualify you for the American Opportunity Credit or the Lifetime Learning Credit! The American Opportunity Credit is partially refundable, meaning you could get up to $1,000 back even if you don't owe taxes. You need Form 1098-T from your school which shows your tuition payments. For the Earned Income Tax Credit, a single person with no qualifying children needs to earn less than about $17,640 in 2025, and be at least 25 years old (with some exceptions). Since you're 19, you might not qualify for EITC yet unless you meet one of the exceptions, but the education credits are definitely worth looking into. This is exactly why general advice like "don't bother filing" can sometimes cause people to miss out on money they deserve!

Oh that makes sense why they were confused when I mentioned the I-9! I just knew it was some form with a letter and number lol. Is there a way I can check if my W-4 is filled out correctly before submitting a new one? I don't wanna mess it up again.

I checked my E*TRADE account and couldn't find anything like that. Is this something I need to specifically request from them or from my employer?

E*TRADE should have something similar, but it might be called something different like "Cost Basis Statement" or "Equity Awards Tax Information." Try looking in the Tax Documents section specifically. If you can't find it there, you might need to contact your company's stock admin team rather than E*TRADE directly. Sometimes the employer has to authorize the broker to provide that supplemental information. For anyone who can't find this document, an alternative is to look at your last December paystub or your W-2, find the total RSU income reported there, and match it to your vesting statements to calculate the proper basis yourself.

Did you have to pay penalties when you filed the amended return? I'm in the same boat and just realized I messed up last year's taxes.

Did you set up the LLC before or after buying the lot? I already own my lot personally, and I'm wondering if transferring it to an LLC would trigger any transfer taxes or other issues.

I already owned the lot personally before setting up the LLC. In my state (Colorado), I was able to transfer the property to my LLC using a quitclaim deed. I did have to pay a nominal recording fee, but there wasn't any transfer tax in my case since it was essentially transferring to myself. However, this varies significantly by state and locality. Some areas have substantial transfer taxes, and the transfer might also affect property tax assessments. There's also the question of how a lender might view the transfer if you have a mortgage or plan to get construction financing. I'd recommend checking with a local real estate attorney about the specific requirements in your area.

That's a good point about ongoing costs! In my state (Michigan) the annual fee is only $75, so it's much less of a consideration. Definitely shows how important location is for this decision.

12 Where exactly is this bulk entry option? I have over 100 transactions from Robinhood and I'm dreading entering them one by one.

3 When you're in the Sale of Stocks, Bonds, etc. section, after you've entered a transaction or two, look for a link that says something like "Enter multiple transactions at once" or "Bulk import" - it should be near the bottom of the screen. It lets you either paste in data from a spreadsheet or upload a file. If you have the Robinhood CSV or Excel download of your transactions, you may need to rearrange the columns to match FreeTaxUSA's expected format. They typically want: Description, Date Acquired, Date Sold, Proceeds, Cost Basis, in that order.

6 This is actually a common issue, especially with crypto or newer stocks. When you see "cost basis not reported to the IRS" on your 1099-B, you still need to enter your actual cost basis in FreeTaxUSA. The IRS requires you to report the correct information even if your broker didn't provide it to them. In FreeTaxUSA, when entering these transactions, there should be a checkbox or option to indicate "Basis not reported to the IRS." Make sure to check this and then enter your actual cost basis. You'll want to keep records of your purchase price in case of an audit.