Has anyone mentioned the whole DBA situation? If his W9 is for an e-card company "doing business as" a video company, are you sure you're even paying the right entity? This sounds super sketchy, and I'd want to verify that the EIN on the W9 actually belongs to a legitimate S-Corp before worrying about the 1099 issue.

You absolutely did make an error sending the 1099 to an S-Corp - they're generally exempt from receiving 1099s since they handle their own tax reporting as a corporation. However, your contractor's reaction seems way over the top for what's honestly a pretty common mistake. Here's what you need to do: File a corrected 1099-NEC (Form 1099-C) showing $0 for the payment amount. This officially cancels out the original form with the IRS. You should do this reasonably soon, but it's not an emergency situation that's going to "destroy their taxes" as they're claiming. That said, I'm more concerned about the sketchy business setup you described. An e-card company DBA as a video production company raises some red flags. Before you do anything else, I'd verify their S-Corp status through your state's Secretary of State business lookup and make sure the EIN on their W9 actually matches a legitimate registered S-Corporation. If something doesn't add up there, you might have bigger issues than just sending the wrong tax form. The whole situation sounds like the contractor is deflecting attention from their questionable business structure by making you feel guilty about a routine paperwork error.

Just a heads up from someone who filed an amended return recently - the IRS is SUPER backed up with processing these. My amended return for 2020 took over 14 months to process. If you're still within your window to amend, file ASAP and expect a long wait. The "Where's My Amended Return" tool on the IRS website didn't update for months even though they had received my paperwork. The good news is that if you're owed a refund, they'll pay interest on it!

Based on what everyone's shared here, it sounds like you're unfortunately past the deadline since you filed your original return on April 15, 2019. The 3-year window closed on April 15, 2022, regardless of the extension you filed but didn't use. However, a few things worth double-checking: 1. Emily mentioned the substantial omission rule - if you're adding income that's more than 25% of what you originally reported, you might have more time 2. Check if you made any tax payments after filing your return - the 2-year rule from payment date might apply 3. If your amendment results in owing MORE tax (not claiming a refund), the IRS will generally accept it at any time I'd strongly recommend getting professional tax advice for your specific situation rather than relying on forum posts. Given the complexity and potential penalties involved, it's worth paying for a consultation with a tax professional or CPA who can review your actual documents and give you definitive guidance. Don't give up just yet - there might be options depending on the specifics of what you're trying to amend!

This is such a helpful thread! I'm dealing with a similar situation where I want to gift some Nvidia shares to my grandson for his college fund. Based on what everyone's shared here, it sounds like I should definitely use specific identification to choose which shares to transfer rather than just defaulting to FIFO. One question though - does the timing of when I actually execute the gift matter for tax purposes? Like if I set up the transfer in December but it doesn't complete until January, which year does it count for gift tax purposes? And does that affect which tax year my grandson would report any gains if he sells them relatively quickly? Also really appreciate the mentions of taxr.ai and Claimyr - going to check both out since my broker (Schwab) has been just as unhelpful as Vanguard was for the OP!

Just wanted to add something that might help with your Vanguard situation - I had a similar experience where customer service wouldn't explain the tax implications, but I found their online resource center actually has some decent explanations about cost basis methods for gifts and transfers. The key thing to understand is that when you gift shares, you're essentially passing along your "tax history" with those shares to your niece. The cost basis method you select determines exactly which shares (with their specific purchase dates and prices) get transferred. Since you've held these tech stocks for 7 years, you probably have multiple "tax lots" purchased at different times and prices. FIFO (which you selected) means you're giving away your oldest shares first. This could be good or bad depending on whether those early purchases were at higher or lower prices than your more recent ones. If the stock price has generally gone up over those 7 years, FIFO would transfer your lowest-cost-basis shares, meaning higher potential capital gains for your niece when she sells. For future reference, "specific identification" gives you the most control - you can literally pick and choose which exact shares to transfer based on what's most tax-advantageous for your niece's situation. But since you already completed the transfer, don't stress too much about it. The main thing is that you documented everything properly for both your records and hers.

Tax professional here. The confusion stems from misinterpretation of TurboTax's marketing. Under IRC §6402 and Treasury Regulation §301.6402-2(e), the IRS maintains sole authority over refund disbursement timing. The Direct Deposit Date (DDD) on your transcript represents the official date when the Treasury will initiate the ACH transfer to your financial institution. TurboTax's expedited service primarily accelerates their internal review process prior to IRS submission, not the actual IRS processing timeline. For accurate financial planning, rely exclusively on the DDD shown on your transcript.

I went through this exact same situation with TurboTax two years ago and learned the hard way! I paid for their expedited service thinking I'd get my refund earlier, but it turns out the "expedited" part only applies to how quickly they process and submit your return to the IRS - not how fast the IRS processes it. The DDD (Direct Deposit Date) on your transcript is definitely the date to plan around. That's when the IRS will actually release your funds. Some banks might make the money available a day early, but that's bank-specific and not guaranteed. I'd recommend budgeting based on the DDD to be safe, especially with kids' activities coming up. Better to have the money earlier than expected than to be short when you need it!

Check your 2023 tax bracket. For married filing jointly: 10% - $0 to $22,000 12% - $22,001 to $89,450 22% - $89,451 to $190,750 24% - $190,751 to $364,200 Your combined income puts you partly in the 22% bracket and partly in the 24% bracket. The witholding tables don't handle two high incomes well. Try this: Multiply what you currently owe ($5,500) by 1.3 (to give a cushion), which is $7,150. Divide by the number of pay periods remaining in the year between both of you. Add that as "additional withholding" on line 4(c) of both your W-4 forms.

I completely understand your stress, especially with a baby coming so soon! Your tax calculation looks correct unfortunately - you're experiencing the "marriage penalty" that affects dual high-income households. The core issue is that you're both earning good incomes ($75K and $130K), putting your combined household income at $205,800. This pushes you into higher tax brackets (22% and touching 24%), but the W-4 withholding system assumes each job is the only household income when you both select "Married." Here's what I'd recommend for immediate action: 1. **Pay the $5,500 now** to avoid penalties and interest 2. **Both update your W-4s immediately** - select "Married but withhold at higher single rate" 3. **Add extra withholding** - roughly $200-250 per paycheck between both of you For peace of mind, use the IRS Tax Withholding Estimator at irs.gov - it's free and will give you exact numbers for your situation. The good news: Next year will be much better! With your new baby, you'll get: - $2,000 Child Tax Credit (fully refundable up to $1,500) - Potential Child and Dependent Care Credit if you use daycare - These credits alone could reduce your tax liability by $2,000+ Don't stress too much - this is a very common issue for dual-income households, and you have the savings to handle it. Focus on adjusting withholding now and enjoying your upcoming arrival!