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.

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.

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!

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!

Just wanted to confirm what others have said - you're definitely in the clear with accounts under $2000! I had a similar situation with freelance income from abroad and was worried I'd missed something important. One thing that helped me was creating a simple spreadsheet to track my foreign account balances monthly. Even though I knew I was well under the thresholds, it gave me peace of mind and would be useful documentation if I ever needed it. I included the account name, currency, local balance, USD equivalent using year-end exchange rates, and any income generated. The key takeaway from my research and experience: income reporting (which you've done correctly on Schedule C) is completely separate from account reporting requirements. Since you're under both the FBAR $10,000 threshold and the much higher Form 8938 thresholds, you only need to worry about that Schedule B checkbox if you had any interest income from the accounts. Keep doing what you're doing - you've handled this correctly!

I've been in a very similar situation and can confirm you're handling this correctly! With foreign accounts totaling under $2000, you're well below both the FBAR $10,000 threshold and the much higher Form 8938 thresholds. One thing I learned from my tax advisor that might help: even though you don't need to file FBAR or Form 8938, make sure to document your maximum account balances throughout the year (not just year-end balances). This is helpful in case your financial situation changes in future years and you approach the reporting thresholds. Also, don't forget about Schedule B Part III - if your foreign accounts generated any interest income (even just a few dollars), you'll need to report that interest income and check "Yes" for having foreign accounts on Schedule B, separate from the FBAR requirements. You've already done the most important part by properly reporting the freelance income on Schedule C. The account reporting requirements are completely separate from income reporting, and with your low balances, you're in the clear on the account side. Keep good records and you'll be fine!