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.

Has anyone had experience with the taxable portion of fellowships and scholarships? My program gave me a "fellowship" but didn't withhold any taxes, and now I'm freaking out about possibly owing a bunch.

This is such a common situation for grad students! Just want to add that even if you don't technically need to file, it might still be worth doing if you had any federal taxes withheld from work-study jobs or other campus employment. You'd get those taxes refunded even with zero income. Also, regarding the Lifetime Learning Credit - the key thing to remember is that whoever claims you as a dependent gets to claim the credit for expenses they paid. So if your parents are claiming you as a dependent AND they paid your tuition directly (not through loans in your name), they should definitely look into claiming that $18,500 in qualified expenses. The LLC can be worth up to $2,000 per year, so that's potentially significant savings for your family. One last tip: keep detailed records of all your education expenses, even if you don't file this year. You might need them for future tax years or if your situation changes!

Make sure to check your state's website for the CORRECT MAILING ADDRESS for amended returns! I sent mine to the regular processing address and it took 5 months to get processed because it was in the wrong department.

Great advice everyone! Just wanted to add that you should also check if your state allows you to track amended returns online. Some states have portals where you can enter your SSN and amended return info to see the status, which is super helpful especially if you're anxious about whether it was received and processed. Also, if you're getting a refund from your amendment, it typically takes longer to process than regular returns - sometimes 12-16 weeks instead of the usual 4-6 weeks. So don't panic if it seems to be taking forever! The certified mail receipt will be your proof that you filed on time if there are any questions later. One last tip: take photos of all your documents before sealing the envelope, including the completed certified mail form. Digital backup never hurts when dealing with tax stuff!