I'm dealing with a somewhat similar timing issue right now! My partner and I are planning to get married in late December, and after reading through all these responses, I'm now paranoid we're going to mess up the paperwork timing too. Can someone clarify - if we get our marriage license in early December and have our ceremony before December 31st, we should be good to file jointly for 2023, right? The key is making sure both the license AND the ceremony/signing happen before the end of the tax year? Also, @Carmen Diaz, I know this probably wasn't the answer you were hoping for, but at least you found out before filing! Better to deal with the disappointment now than potential IRS issues later. And honestly, reading through everyone's advice here, it sounds like there might be some silver linings to filing separately that you hadn't considered yet.

I'm a CPA and wanted to add some clarification to help with your situation. While everyone is correct that you'll need to file separately for 2023, there's one potential silver lining worth exploring - the "marriage penalty" vs "marriage bonus" calculation. For many couples, especially those with similar incomes, filing separately can actually result in lower combined taxes than filing jointly would have. This is because the married filing jointly brackets aren't exactly double the single brackets, and certain deductions have different phase-out limits. I'd recommend running the numbers both ways (what you'll pay filing separately vs what you would have paid filing jointly) using tax software. You might be surprised to find that the difference isn't as significant as you expected, or in some cases, you might even come out ahead. Also, make sure you're both maximizing your 401(k) contributions for 2023 if you haven't already - the individual limits are the same whether you're married or single, but your ability to fully deduct traditional IRA contributions might be different based on your separate AGIs rather than combined. The timing is frustrating, but don't let it overshadow your celebration. Congratulations on your marriage!

Pro tip for anyone who's cutting it close to deadline: Take a picture of yourself physically handing over your tax documents to the FedEx/UPS employee along with a photo of the receipt showing the date and time. I've had the IRS question my timely filing before, and having those photos saved me from a penalty.

Something that helped me understand the private delivery service rules better was realizing that the IRS treats these services differently than USPS because they don't have "postmarks" in the traditional sense. With USPS, the postmark date is what matters, but with FedEx/UPS, it's the actual date you hand over the package that counts as your filing date. I always make sure to drop off my tax documents during business hours so there's a clear timestamp on my receipt. If you use a drop box after hours, technically that might be considered the next business day, which could be problematic if you're cutting it close to the deadline. Also worth noting - if you're filing an extension (Form 4868), the same rules apply. The private delivery service has to be on the IRS approved list, and you need that receipt as proof of timely filing.

If you're using TurboTax, be super careful with how you enter this! I had a similar situation and TurboTax completely messed up my self-employed health insurance deduction. It put it on the wrong form and I ended up getting a nasty letter from the IRS.

I'm dealing with a very similar situation right now! I have W-2 income with employer health insurance for myself, but my spouse is on a separate marketplace plan because adding them to my employer plan would cost way more than their individual coverage. I also have an LLC (elected S-Corp) from freelance work. From what I've researched, the key issue is whether your employer coverage "could have" covered your family members, regardless of cost. This is where it gets tricky - technically your employer offers family coverage, even though it's unreasonably expensive at $950/month. Some tax professionals argue that if the employer coverage is prohibitively expensive compared to marketplace alternatives, you can still claim the self-employed health insurance deduction. Others take a more conservative approach and say any availability of employer family coverage disqualifies you. I'd definitely recommend getting professional advice on this specific situation since the IRS guidance isn't crystal clear on what constitutes "reasonably available" employer coverage. The potential tax savings are significant, but you want to make sure you're on solid ground if questioned.

Don't forget about local transportation costs! If you rent a car for both the business and personal parts of the trip, you need to allocate those costs too. Only the days you used the car for business are deductible. Same goes for taxis/Ubers during your trip - only the ones related to business activities count. Like getting from your hotel to the conference venue is deductible, but taking an Uber to go sightseeing isn't.

Great question! I dealt with this exact scenario last year when I had a conference in Denver and decided to stay an extra 10 days to visit friends and ski. Since you're attending the conference August 2-5 and arriving August 1st for business purposes, those 5 days would be considered your business portion. The key thing the IRS looks at is whether your PRIMARY purpose for the trip was business - which it sounds like it was, since you're planning the vacation around an existing business conference. For domestic travel (assuming this is within the US), you should be able to deduct the entire airfare even with the extended personal stay, as long as business was your primary purpose. However, you can only deduct lodging and meals for August 1-5. Everything from August 6th onward would be personal expenses. Make sure to keep detailed records: conference registration, agendas, any business meetings or networking events you attend, receipts clearly marked with dates, etc. I also recommend keeping a simple day-by-day log noting which activities were business vs personal. One tip: if you're doing any business-related activities during your extended stay (like meeting with potential clients or visiting business contacts), those days might also qualify as business days, which could help your allocation if this were international travel.

Quick tip if you're preparing Form 8919 - make sure you enter code G in box c since you've filed the SS-8 but haven't received a determination. Also, you'll need to fill out the employer information in boxes d through f (name, EIN, and address). The other thing people often miss is that the amount from the 1099-NEC goes in column d (Total wages) of Form 8919, and then that same amount needs to be reported on Schedule 1 as "other income" with a note that it's also being reported on Form 8919. This prevents duplicate taxation while ensuring it's properly reported. If the software doesn't seem to be handling this correctly, try entering your 1099-NEC information, but then go back and look for a section about "Forms" or "Miscellaneous Forms" and specifically add Form 8919.

Just wanted to share my experience since I went through this exact situation about 8 months ago. The key thing that helped me was understanding that Form 8919 needs to be treated as a separate form in your tax software, not just an adjustment to your 1099-NEC. In FreeTaxUSA specifically, after you enter your 1099-NEC information, go to the "Federal Taxes" section and look for "Less Common Income" or "Other Tax Situations." There should be an option for "Unreported Social Security and Medicare Tax" or something similar - that's where you'll find Form 8919. When you complete Form 8919, make sure you: 1. Use reason code G (you filed SS-8 but no determination yet) 2. Enter your employer's full information 3. Put the full amount from your 1099-NEC in the wages section The software should then automatically reduce your self-employment tax and only charge you the employee portion of FICA taxes. If it's still showing the full self-employment tax, double-check that the 1099-NEC amount isn't being counted twice in different sections. One last tip - print out your completed return before filing to verify the numbers look right. You should see Form 8919 attached and your total tax should be significantly lower than if you filed as self-employed.