Have you considered filing for an extension? If you're running up against the deadline and aren't sure about the signature requirements, you could buy yourself some additional time to either get a proper wet signature or research alternative filing methods. Just a thought!

Just wanted to share what worked for me in a similar situation last month. I had a client who couldn't come in due to mobility issues, and after researching extensively, I found that the IRS does offer some flexibility for situations like this. You can actually have your client sign a Power of Attorney (Form 2848) electronically, which allows you to sign Form 1096 on their behalf. The POA can be obtained through secure email with proper authentication. This is completely legitimate and I've used it successfully for several clients who couldn't provide wet signatures. Alternatively, if the client can manage it, you could do a video call while they sign the form at home, then have them mail it back to you in a prepaid envelope. This ensures you get the original wet signature the IRS requires while accommodating their health concerns. Both approaches have worked well for me and kept everything compliant with IRS requirements. Hope this helps with your deadline!

My company did this to me last year. Turned out they had me listed as living in Nevada (no state income tax) when I actually live in California (big state income tax). Had to pay almost $3k at tax time. Make sure u check ur address on file with HR!!

This is definitely stressful but you're not alone - this happens more often than you'd think! The empty state tax box does mean no state taxes were withheld all year. First thing I'd do is check your final paystub from 2024 to confirm the year-to-date state withholding shows $0.00. A few things to consider: 1) Double-check that your employer has your correct home address on file - sometimes they withhold for the wrong state or no state if there's an address mix-up, 2) Look into whether your state offers any payment plan options if the amount is large, 3) Definitely get this fixed with payroll ASAP for 2025 so you don't face this again. Also worth noting - if this was your employer's error and not something you requested, you might be able to avoid underpayment penalties by explaining the situation to your state tax department. Document everything in case you need to appeal any penalties later!

Quick question - has anyone dealt with selling shares that are held in an LLC taxed as an S-Corp? I'm getting conflicting advice on whether the installment method can be used in that scenario.

This is a great question that many people don't realize until they're in the middle of it! One important thing to add to the excellent advice already given - make sure you keep detailed records of ALL payments as they come in throughout the year. Create a simple spreadsheet tracking each payment date, amount, and which milestone it corresponds to. Also, consider setting aside 25-30% of each payment for taxes (depending on your tax bracket). Since you're receiving money throughout the year, it's easy to spend it and then get hit with a big tax bill. I learned this the hard way with my first installment sale - ended up scrambling to find cash for quarterly estimated payments. One more tip: if any of your original shares qualify for QSBS (Qualified Small Business Stock), you could potentially exclude up to $10 million or 10x your basis from federal taxes. Definitely worth checking if your company was a C-Corp with gross assets under $50 million when the stock was issued.

Military spouse here! Step 1: Calculate your taxes both ways before deciding. We did MFS last year because my husband was deployed to a combat zone (tax-free income) while I had regular taxable income. Step 2: Document who paid what - we keep separate accounts for this reason. Step 3: If using MFS, each claim your portion of mortgage interest on Schedule A. Step 4: File before the April 15th deadline - it's coming up fast! The mortgage interest split was actually straightforward on our tax software. Just had to enter the 1098 information and then specify what percentage each person paid.

Great question! As a military family myself, I can confirm you absolutely can file separately with a joint mortgage. The key is documenting who actually paid the mortgage interest. Since you're both on the loan, you'll split the 1098 interest based on actual payments made. If paying from a joint account, it's typically 50/50 unless you can prove otherwise with bank records. For military families, MFS can make sense in several scenarios: different state residency situations during PCS moves, combat pay exclusions, income-based student loan repayments, or when one spouse has significant miscellaneous deductions. However, remember both spouses must choose the same deduction method (both standard or both itemize). I'd strongly recommend calculating both MFJ and MFS scenarios before deciding. Military-specific tax software like FreeTaxUSA Military or TurboTax Military can help you compare both filing statuses easily. Also consider consulting with a tax professional who understands military tax situations - many bases offer free tax prep services that are familiar with these complexities.

Be careful about calculating your exact gain! I made a huge mistake when selling my house last year. Your gain isn't just (selling price - purchase price). The actual formula is: Selling price - Selling expenses (realtor fees, etc.) - Purchase price - Purchase expenses (closing costs you paid when buying) - Capital improvements during ownership = Your actual gain I initially thought I had a $280k gain after the exclusion, but after properly accounting for $12k in selling costs, $8k in purchase costs, and about $65k in documented improvements, my taxable gain was only $195k. That saved me thousands in both capital gains tax and NIIT!

Thank you everyone for this incredibly detailed discussion! As someone who's been stressing about this exact situation, this thread has been a goldmine of information. I want to emphasize something that Miguel mentioned about calculating your actual gain - I see so many people (including myself initially) making the mistake of thinking it's just selling price minus what you paid. The reality is that your basis includes not just your original purchase price, but also: - Closing costs when you bought - Major capital improvements (kitchen remodels, new roofs, HVAC systems, etc.) - Selling expenses (realtor commissions, title fees, etc.) I've been keeping a spreadsheet of all my home improvements over the years, but after reading this thread I realized I forgot about my original closing costs from 9 years ago. Just found those documents and it's another $7,200 I can add to my basis! For anyone in a similar situation, I'd strongly recommend gathering ALL your documentation before panicking about the tax implications. Between the $250k/$500k exclusion and properly calculating your actual basis, your taxable gain might be much lower than you initially think. Also planning to try that taxr.ai tool that Giovanni and Dylan mentioned - seems like it could help me organize all this information properly before I meet with my tax preparer.