I went through this exact situation two years ago at 24, and I completely understand the confusion around handling the penalty timing. Here's what I learned from experience: The key thing to remember is that the 10% penalty is calculated on your tax return using Form 5329, but you need to plan for the cash flow impact NOW. I chose to have extra withholding taken out on my W-4R to cover both the regular income tax AND the 10% penalty, and I'm so glad I did. Here's why: when you withdraw early, that money gets added to your regular income for the year, which could potentially bump you into a higher tax bracket. Plus, if you don't have enough total tax withheld throughout the year (including covering that 10% penalty), you might face underpayment penalties on top of everything else. My advice? Calculate 10% of your withdrawal amount, add it to your estimated regular income tax on that money, and have it all withheld. Yes, you're giving the government an interest-free loan for a few months, but the peace of mind is worth it. I sleep much better knowing I won't get hit with a surprise tax bill next April! Also, definitely double-check if you qualify for any penalty exceptions - medical expenses, first-time home purchase, higher education costs, etc. could save you that entire 10%.

I went through this exact situation when I was 22 and had to make an early withdrawal for emergency expenses. Here's what I wish someone had told me upfront: The IRS doesn't require you to prepay the 10% penalty, but here's the catch - if you don't plan for it properly, you could end up owing estimated tax penalties under Section 6654. I learned this the hard way! What worked for me was using the IRS withholding calculator on their website along with my withdrawal amount to figure out exactly how much extra to withhold. I had my plan administrator withhold about 32% total (22% for income tax + 10% penalty) rather than their default 20%. One thing that really helped me was calling my 401k plan administrator directly. They walked me through exactly how to adjust the withholding on my distribution request. Most people don't realize you can usually specify the exact withholding percentage when you request the withdrawal. Also, definitely keep all your paperwork! You'll need the 1099-R when you file, and if you qualify for any exceptions (like the ones Emily mentioned - medical expenses, education, first-time home purchase), you'll want documentation ready. The math is straightforward, but getting the withholding right upfront saved me from a stressful tax season. Better to have them hold a bit extra now than scramble to come up with cash next April!

Anyone know if using the truck for business will affect insurance? My personal auto policy threatened to cancel me when they found out I was using my truck for business deliveries.

Just wanted to chime in as someone who went through this exact situation with my contracting business. You're absolutely on the right track - the title being in your personal name won't prevent you from claiming Section 179 on your Tundra. One thing I'd add to the great advice already given: make sure you're also tracking your financing costs correctly. Since you financed $29,000 of the purchase, you can deduct the business portion of the interest payments as well. With 80% business use, that's 80% of your monthly interest that becomes deductible. Also, start that mileage log immediately if you haven't already! The IRS wants to see contemporaneous records, so retroactively creating a log for the whole year can raise red flags during an audit. Even a simple app like the basic smartphone mileage tracker works fine - just be consistent with logging every trip. The $28,200 limit mentioned earlier is spot on for 2025, and with your $33,600 business portion, you'll hit that cap and save a significant amount on your taxes. This is one of the best deductions available to small business owners with heavy vehicles!

Another tip - make sure you're looking at the correct tax year's forms. Sometimes 1099-Bs include transactions from previous December if they settled in January of the reporting year. Also check if your company provides a supplemental tax document specifically for equity compensation - many do!

Great advice from everyone here! I went through this exact same confusion last year with my company's RSUs. One thing that really helped me understand the discrepancy was getting a detailed breakdown from my brokerage. Most brokerages have a "tax center" or "tax documents" section on their website where they provide supplemental information that explains how your 1099-B relates to your equity compensation. For example, my brokerage (Schwab) had a separate document that showed: - Each vesting event and the FMV on that date - Which shares were sold to cover taxes vs. sold voluntarily - How the cost basis was calculated for each transaction This made it crystal clear why my W2 (showing total vesting value) was different from my 1099-B (showing only actual sales). The key insight was that some of my "sales" weren't actually me selling - they were automatic tax withholding sales that happened at vesting. Definitely check your brokerage's tax center before panicking! And yes, as others mentioned, you'll report both the W2 income AND the 1099-B transactions - they serve different purposes in the tax calculation.

Have you checked both Account Transcript and Return Transcript? Sometimes one appears before the other. What about checking transcript for prior years - are those available? Could be an account access issue rather than processing delay. Did you receive an acceptance confirmation from your software after filing? What's your current WMR status?

I'm currently on day 12 since filing electronically and still seeing "N/A" on my transcript portal. Reading through everyone's experiences here is really helpful - it sounds like the 7-21 day range is pretty normal. I filed a relatively simple return (W-2 income only, standard deduction) on February 28th, so I'm hoping it shows up soon. The waiting is definitely stressful, especially when you're checking multiple times per day! Has anyone noticed if checking the portal too frequently affects anything, or is that just my anxiety talking?