I completely understand your anxiety about this! As someone who's been through the S-Corp extension process multiple times, I can tell you that the lack of confirmation in your client portal is actually pretty normal - many firms don't automatically upload extension confirmations. Here's what I'd recommend for immediate peace of mind: Email your accounting firm and specifically ask for the "electronic filing acknowledgment receipt" or "e-file confirmation" from their tax software. This should include a timestamp and confirmation number proving the extension was transmitted. Any reputable firm that filed electronically should be able to provide this within minutes. If you want to verify independently, the IRS Business Tax line (800-829-4933) can confirm if an extension is on file, but I'd suggest calling right when they open at 7 AM for the shortest wait times. Have your EIN ready. One thing that might ease your worry: if there had been an issue with the electronic filing, you typically would have received a rejection notice by now. The IRS processes electronic extensions pretty quickly and sends rejection notifications within a few days if there are problems. Don't feel bad about following up with your accountant - this is a completely reasonable request and getting that documentation will give you the peace of mind you need to focus on your business instead of worrying about compliance issues!

I went through this exact anxiety last year with my first S-Corp filing! Here's what finally gave me peace of mind: The fastest way to verify is actually through the IRS Business Online Account if you can get it working (try different browsers - Edge worked better for me than Chrome). If that's not working, calling the Business Tax line at 800-829-4933 first thing in the morning (7 AM sharp) usually gets you through faster. But honestly, the quickest solution is to just email your accounting firm and ask for the "electronic filing acknowledgment" from when they submitted Form 7004. This isn't an official IRS document, but it's the receipt from their tax software showing the extension was successfully transmitted with a confirmation number and timestamp. They should be able to send this to you within minutes if they filed electronically. If they can't produce that acknowledgment immediately, that would be concerning. But if they can show you the e-file receipt, you'll have instant proof it went through. One thing that helped calm my nerves: the IRS sends rejection notices pretty quickly for electronic filings (usually within 2-3 days), so if you haven't received any rejection notices, that's actually a good sign. Don't feel awkward about asking - this is your business and you absolutely have the right to documentation that critical tax deadlines are being met!

Just to add another wrinkle - if your $4000 withdrawal included any dividends from those stocks (not just capital gains from selling), those are taxed differently. Qualified dividends get favorable tax rates similar to long-term capital gains, while non-qualified dividends are taxed at your ordinary income rate. Your 1099-DIV from the brokerage should break this down for you. Just something else to be aware of!

This is all really helpful information! I'm in a similar boat as Sophia - first time dealing with investment taxes and feeling pretty overwhelmed. One thing I'm still confused about is the timeline. Since I sold stocks earlier this year, do I need to pay estimated quarterly taxes on those gains, or can I just wait until I file my regular tax return next year? I keep hearing conflicting things about whether you need to make estimated payments if you have capital gains, especially if it's your first time having investment income. Don't want to get hit with penalties if I'm supposed to be paying something now!

Just a heads up for anyone preparing 2022 returns with NOLs carried forward from 2018-2020 - remember those aren't subject to the 80% limitation due to the CARES Act provisions. Only NOLs from 2021 forward have the 80% limitation. I've seen several colleagues mistakenly apply the 80% limitation to all NOLs.

This is exactly the kind of complex scenario that highlights why NOL calculations can be so tricky! I've dealt with similar situations and want to add a few practical tips that have helped me: First, when you're doing the iterative calculations that others mentioned, I found it helpful to set up a simple Excel worksheet with columns for: Iteration #, AGI before NOL, Social Security taxable amount, Taxable income before NOL, 80% limitation amount, and Final taxable income after NOL. This makes it easy to see the convergence pattern and provides documentation for your files. Second, I've noticed that the circular calculation usually stabilizes within 3-4 iterations, but occasionally with very specific income ranges near the Social Security benefit thresholds, it can take 5-6 iterations. Don't panic if the first few rounds seem off - just keep going until the numbers stop changing. One thing I haven't seen mentioned yet is to double-check your state return if applicable. Some states don't conform to the federal 80% limitation or have their own NOL rules that could create additional complications. California, for example, has suspended NOL deductions entirely for certain tax years. Great discussion everyone - this is exactly the kind of real-world problem-solving that makes this community so valuable!

When I bought my company car, HR gave me a fancy official bill of sale that had a separate line for sales tax. Make sure u get something like that!! Some states also have special forms for this situation. In my state they had a specific form (MV-82B I think?) that showed the tax was already paid. Without it I woulda been charged again at DMV for sure lol!

This is actually pretty standard practice when buying from a business entity, including your employer. I went through this same process when I bought a company vehicle a few years ago and was initially confused too. The key difference is that businesses are registered tax collectors with the state, so they're required to collect and remit sales tax on vehicle sales just like a dealership would. When you buy from a private party, neither you nor the seller is a registered tax collector, so you handle it at the DMV. Make sure you get a detailed bill of sale that clearly itemizes the sales tax amount, includes the vehicle VIN, and shows your company's tax ID number. This documentation will be crucial when you register the vehicle - it proves the tax was already collected and prevents double taxation. Most states have systems where this gets reported electronically, so the DMV should already know the tax was paid when you show up to register. Your $1,320 in sales tax on a $16,500 purchase sounds about right for most states (around 8% rate). Just make sure all the paperwork is properly documented and you should be good to go!

Have you considered just taking a distribution from your other business to pay for this, rather than reducing your estimated tax payments? Underpaying your estimated taxes could result in penalties and interest if you end up owing more than you paid in quarterly payments.

Before you reduce your estimated tax payments, make sure you understand the penalty implications. The IRS generally requires you to pay either 90% of the current year's tax liability or 100% of last year's tax (110% if your prior year AGI exceeded $150,000) through withholding and estimated payments to avoid underpayment penalties. If you're planning to pay $26.5k instead of $33k this quarter, you need to verify that your total payments for the year will still meet the safe harbor requirements. The underpayment penalty is calculated quarterly and can be substantial - currently around 8% annually. A safer approach might be to take a proper distribution from your other business to fund the website expense, then handle it as a capital contribution to the partnership as others have suggested. This keeps your estimated tax payments on track while still allowing you to personally fund the website expense.