Can you reach out to any other family members who might be able to help as a go-between? Sometimes having a neutral third party can help in these situations. Otherwise Form 4852 is exactly what it's designed for - situations where you can't get a W-2 but need to file your taxes.

I'm dealing with a similar family business situation right now, so I really feel for you. One thing that might help is checking if your family's business uses any payroll service like ADP, Paychex, or QuickBooks Payroll. Sometimes you can get your W-2 directly from the payroll company's website even if you can't contact your employer directly. Also, if you have any old login credentials for a payroll portal or employee self-service site, those might still work. I was able to download my W-2 from our family business's ADP portal even after leaving because they never deactivated my account. If those options don't work, Form 4852 really is your best bet. The IRS designed it specifically for situations like yours where getting the W-2 isn't realistic. Just be as accurate as possible with your estimates and keep any documentation you have (paystubs, bank deposits, etc.) in case they ask questions later.

Thanks for all the helpful responses everyone! Just wanted to give a quick update - I went ahead and used my husband's SSN (primary taxpayer) in Direct Pay and the payment went through smoothly. Got a confirmation number and everything. I really appreciate everyone clarifying that even though I'm the one earning the freelance income, the IRS system only recognizes the primary taxpayer's info for joint filers. That makes total sense now that I understand how their computer systems work. I'm definitely going to look into some of the tools mentioned here (like taxr.ai) to help me calculate the right amounts for future quarters. I've been kind of winging it with estimated payments and want to make sure I'm not underpaying and getting hit with penalties. One last question - should I be making these payments every quarter even if my freelance income varies a lot month to month? Sometimes I have big projects and sometimes barely anything. Is it better to estimate conservatively and potentially overpay, or try to match the actual income more precisely each quarter?

One thing I'd add to the safe harbor discussion - you can also use the "annualized income installment method" if your freelance income is really sporadic throughout the year. This lets you calculate each quarterly payment based on your actual income for that specific period, rather than spreading an annual estimate evenly across four quarters. It's more paperwork (you'll need to file Form 2210 with your return), but it can save you money if most of your income comes in just one or two quarters. For example, if you have a huge project in Q3 but barely any income in Q1 and Q2, you could make smaller payments early in the year and a larger payment in Q3 when you actually earned the money. The downside is it's more complex to calculate and track. For most people with moderately variable income, the safe harbor approach that Mateo mentioned is much simpler and still protects you from penalties. But if your income swings are really dramatic (like making 80% of your annual freelance income in one quarter), the annualized method might be worth looking into.

This has been such an incredibly thorough and educational discussion! As someone who's been dealing with NOL carryforwards from a business that didn't work out as planned, I really appreciate how comprehensively everyone has covered the NOL and capital gains intersection. The key takeaways I'm getting are: 1) Yes, NOLs can offset capital gains including from real estate sales, 2) There's an 80% limitation for post-2020 NOLs, 3) State tax rules may differ significantly from federal rules, and 4) The optimization requires looking at multiple years, not just the current tax year. What really strikes me is how this discussion evolved from a basic question about NOL rules into a masterclass on integrated tax planning. The interactions with NIIT, depreciation recapture, suspended passive losses, Roth conversions, and even broader investment strategy considerations show just how interconnected tax planning really is. I'm definitely going to follow the advice about getting comprehensive multi-year tax projections rather than just a consultation. Given all the variables discussed here, it's clear that optimizing NOL usage properly requires professional modeling that accounts for federal taxes, state taxes, timing strategies, and your broader financial goals simultaneously. Thanks to everyone who shared such detailed expertise - this is exactly the kind of collaborative knowledge-sharing that makes complex tax decisions much more manageable!

This has been an absolutely phenomenal discussion that's covered virtually every angle of NOL and capital gains planning! As someone who works in tax preparation during the busy season, I wanted to add a few practical insights that might help others in similar situations. One thing that hasn't been fully emphasized is the importance of timing your NOL usage with your overall income pattern. If you expect to be in a higher tax bracket in future years (due to business recovery, spouse returning to work, etc.), it might make sense to preserve some NOLs for those higher-income years, even with the 80% limitation. Also, for those dealing with multiple types of carryforwards (NOLs, capital loss carryforwards, charitable contribution carryforwards), the order of application matters and can affect your optimization strategy. NOLs are generally applied after most other deductions, which can create some interesting planning opportunities. Finally, I'd strongly recommend documenting your NOL planning decisions and rationale. The IRS has been increasing scrutiny of NOL claims in recent years, especially for taxpayers with significant carryforward amounts. Having clear documentation of your planning process and professional advice can be invaluable if questions arise later. The collaborative expertise shared in this thread has created an incredibly valuable resource for anyone dealing with NOL complexities. This is exactly why professional communities like this are so important for navigating our ever-changing tax landscape!

I'm in the same boat but decided to go ahead and file without the donations this year. My donations only add up to about $750 in value, so it's only changing my refund by like $90. Not worth waiting weeks for that small amount when I'm getting back $3400 otherwise.

I've been dealing with this exact same frustration! After reading through all these comments, I ended up trying a hybrid approach. I used taxr.ai to organize all my donation receipts (which was honestly a lifesaver - had boxes of stuff from multiple charities), and then called the IRS using Claimyr to get an actual timeline. The IRS agent confirmed that Form 8283 should be available by January 28th, but she also mentioned something important - they're implementing new validation rules this year that might flag certain donations for review. She suggested keeping really detailed records of item conditions and fair market value calculations, especially for anything over $500. For anyone on the fence about waiting vs filing now, I'd say it depends on your donation amounts. I have about $2800 in donations which translates to roughly $400 in tax savings, so I'm waiting the extra week. But if you're only looking at $50-100 in tax benefits, probably not worth the hassle.

Ok so now I'm thoroughly confused! I have an LLC taxed as an S-corp... on the W-9, do I check LLC and write S, or do I just check S-Corp box??

This is such a common source of confusion! As someone who went through this exact same struggle when I first set up my LLC with S-Corp election, I totally understand the frustration. To clarify what others have said: if you formed an LLC (filed Articles of Organization with your state) and then elected S-Corporation tax treatment with the IRS (Form 2553), you are still legally an LLC. The S-Corp election only changes how the IRS taxes your business income - it doesn't change your actual business entity type. So on the W-9, you should: 1. Check the "Limited Liability Company" box 2. Write "S" on the line that asks for tax classification The "S-Corporation" checkbox is for businesses that were actually incorporated as corporations (filed Articles of Incorporation) and then elected S-Corp status. That's a different legal structure entirely. One tip: I always include a brief note on my W-9s that says something like "LLC electing S-Corp tax treatment per Form 2553" just to be extra clear. It helps avoid confusion with clients who might not understand the distinction and ensures the 1099s come back correctly.