Has anyone used tax software like QuickBooks or TaxAct for this? I have a similar situation with my S-Corp and wondering if the software handles these unrealized losses automatically or if I need to make manual adjustments.

I went through this exact same situation with my S-Corp last year and it was definitely confusing at first. The advice about Schedule M-1 line 5 is spot on - that's exactly where the unrealized loss goes. One thing I'd add is to make sure you document everything clearly in case of an audit. I kept a simple spreadsheet showing the original purchase price ($1,200), year-end fair market value ($550), and the calculation of the unrealized loss ($650). This helps if you ever need to explain the M-1 adjustment. Also, don't forget that when you eventually sell these stocks, you'll need to reverse this M-1 adjustment since the actual gain/loss will be recognized for tax purposes at that point. The unrealized loss adjustment is temporary - it just reconciles the timing difference between book and tax accounting. Your balance sheet approach sounds correct too - showing the securities at fair market value ($550) with the unrealized loss flowing through to reconcile your retained earnings. It all balances out once you get the M-1 schedule right.

Great question! I went through something very similar last year. You're absolutely right that you can deduct up to $3,000 of your capital losses against your ordinary income. Since you have $4,000 in losses and no gains to offset them, you can deduct $3,000 this year and carry the remaining $1,000 forward to next year. One thing to double-check though - make sure none of your sales triggered wash sale rules. If you sold any stocks at a loss and then bought the same or "substantially identical" securities within 30 days before or after the sale, the IRS disallows that loss deduction. This is a common trap that catches a lot of people. You'll report these losses on Schedule D of your tax return, and the net capital loss will flow to line 7 of your Form 1040. If you're in a decent tax bracket, that $3,000 deduction could save you several hundred dollars in taxes - not a huge consolation for the losses, but at least Uncle Sam shares in your pain a little bit! Keep good records of that $1,000 carryover for next year's filing. Most tax software handles this automatically, but if you're doing it manually you'll want to make note of it.

I've been through this exact situation and can confirm what others have said - yes, you can absolutely deduct up to $3,000 of your capital losses against your ordinary income! Since you lost $4,000 and have no capital gains to offset, you'll be able to deduct $3,000 this year and carry forward the remaining $1,000 to next year. Just make sure you didn't accidentally trigger any wash sales by repurchasing the same stocks within 30 days of selling them at a loss. That's a common mistake that can disallow your deduction. The silver lining here is that your $3,000 deduction could save you anywhere from $360-$1,110 in federal taxes depending on your tax bracket (12% to 37%). You'll report this on Schedule D and it flows through to reduce your adjusted gross income on Form 1040. Keep good records of your trades and that $1,000 carryover amount for next year. At least we can get some tax relief from our investing mistakes - it's one of the few times the tax code actually works in favor of the little guy who's had a rough year in the markets!

Andre, you've gotten some fantastic advice here! As someone who works in tax preparation, I can confirm everything everyone has said - absolutely no penalties for filing late when you're owed a refund. The IRS only penalizes late filing when you owe them money. One thing I'd add that might help ease your mind: even at 4 months late, you're not even close to being "really late" in IRS terms. I regularly help clients who are filing 1-2 years late for refunds, and they face no issues whatsoever as long as they're within that 3-year window. Since you mentioned over-withholding and having a child, you're likely looking at a decent refund between your regular withholdings and the Child Tax Credit. Don't let the complexity of the move and new job intimidate you - most tax software handles multi-state situations pretty well these days. My advice? Set aside a weekend, gather your documents, and just get it done. The relief you'll feel having it off your plate (plus getting your refund money) will be totally worth the effort. And next year, consider setting a calendar reminder for yourself in February to start gathering documents early - it'll save you this stress! You've got this! The hardest part is just starting.

Andre, I'm new to this community but your situation really resonates with me! I went through almost the exact same thing when I relocated for work - completely overwhelmed with the move and let taxes slip through the cracks. Everyone here has given you excellent advice confirming there are no penalties when you're owed a refund. What really helped me when I was paralyzed by the complexity was breaking it down into smaller steps. Start by just gathering your documents - W-2s, any 1099s, receipts from the move and job search. Don't worry about filing yet, just get organized. Given your situation (new job, cross-country move, child), you're likely looking at a substantial refund between over-withholding and the Child Tax Credit. I ended up getting back way more than expected because of similar circumstances - moving expenses may be limited now, but there are often other deductible costs from job transitions that add up. The peace of mind you'll get from finally tackling this will be huge. Plus, with a little one, that refund money could probably really help right now! Set aside a weekend, get your documents together, and just dive in. You've got this!

Has anyone else noticed that tax software companies seem to move more forms to their paid tiers every year? I swear H&R Block included Schedule B in their free version back in 2022.

This is exactly the kind of predatory practice that makes tax season so frustrating for regular people. You're absolutely right that Schedule B isn't required for $4 in dividends - the IRS threshold is $1,500, and tax software companies know this but deliberately create confusion to drive upgrades. I've seen this same issue with multiple tax prep companies. They detect any dividend income and immediately flag you for their premium service, even when it's completely unnecessary. It's particularly frustrating because they market their "free" versions heavily but then hit you with these surprise charges right when you're trying to file. Since you've already invested time in H&R Block, I'd suggest trying the workaround that Fatima mentioned - temporarily removing the dividend entry to get past their upgrade checkpoint, then adding it back on the main 1040 form where it belongs. If that doesn't work, FreeTaxUSA and IRS Free File are solid alternatives that won't nickel and dime you for basic forms. The fact that your situation is identical to last year but suddenly requires an "upgrade" tells you everything you need to know about their business model. Don't let them bully you into paying for something you don't legally need.

Just FYI as a tax preparer, bring ALL your medical receipts to your appointment, not just COBRA. Many people forget about mileage to medical appointments (17 cents per mile for 2024), prescription costs, dental expenses, eye care, medical equipment, etc. Every dollar helps get you closer to that 7.5% threshold.

Great question about COBRA and taxes! Just wanted to add one important point that might help you save money - if you have any self-employment income from your freelance work, you might qualify for the self-employed health insurance deduction for your COBRA premiums. This is WAY better than the itemized medical expense deduction because it's an above-the-line deduction (meaning it reduces your AGI directly) and you can still take the standard deduction. Since you mentioned having 1099 income, definitely ask your tax preparer about this. The self-employed health insurance deduction lets you deduct health insurance premiums (including COBRA) as long as you have net self-employment income and you're not eligible for coverage through your spouse's employer plan. Given that you're both on COBRA, this could be a huge tax saver. For documentation, bring your 1099s showing the freelance income and all your COBRA payment records. The preparer can determine if this applies to your situation - it could potentially save you way more than trying to meet that 7.5% AGI threshold for itemized medical expenses!