FYI - I went through an IRS review last year for unreported income that was paid through various apps. Even though I didn't receive any official tax forms, the IRS still had records of large regular payments coming into my accounts. They can access way more info than people realize! If you're getting paid through Zelle from a business account, definitely report it properly. Calculate all your business expenses too - track mileage, home office, equipment, etc. The WORST thing is getting hit with taxes on the full amount when you could have reduced it with legitimate deductions.

I was in almost exactly this situation two years ago - getting paid through Zelle from an LLC with no paperwork. Here's what I learned the hard way: report it ALL as self-employment income on Schedule C, even without a 1099. The key things that helped me: 1. Export your bank statements showing all Zelle payments from their LLC 2. Calculate your total annual income from this work 3. Track ALL business-related expenses (gas, phone, supplies, etc.) to offset the income 4. Set aside about 25-30% of your earnings for taxes since you'll owe both income tax and self-employment tax I initially thought about not reporting it since there were no forms, but my accountant scared me straight - the IRS can see bank deposits and regular payments from business accounts are red flags. Better to be proactive and honest than deal with penalties and interest later. Also, start making quarterly estimated tax payments for next year if this income will continue. Trust me, owing a huge lump sum at tax time is brutal!

I found that the "Where's My Refund" tool on IRS.gov sometimes shows a message about offsets when they occur. It's worth checking there too. The IRS2Go app sometimes shows this info as well. I was shocked at how many different places I had to check to piece together what happened to my refund last year! The system definitely isn't designed to make this easy to understand.

As a military family going through PCS, I'd strongly recommend checking the Treasury Offset Program immediately at 800-304-3107 rather than waiting. Military moves have tight timelines and you need to know exactly what funds you'll have available. Also, since you mentioned you're military, be aware that the Servicemembers Civil Relief Act (SCRA) provides some protections against certain types of debt collection, though it doesn't prevent all offsets. Your base legal assistance office can clarify which debts might still be subject to offset even with SCRA protections. Better to know now than discover a surprise offset when you need those funds for your move!

Just to throw another option out there - could you hire your friend as a consultant or for some administrative work they could do remotely? Then it becomes a legitimate business expense, and they get income they can use for medical bills. You'd need to make sure they actually provide services and you document everything well, but it might be more straightforward than setting up a charity.

I really appreciate everyone's thoughtful responses here. As someone new to this community, I'm dealing with a similar situation where my small business wants to help a family member with medical expenses. From reading through all the comments, it seems like the key takeaway is that direct donations to individuals aren't deductible no matter how you label them, but there are some legitimate alternatives worth exploring. The suggestions about QSEHRAs and Medical Expense Reimbursement Plans caught my attention, especially if there's genuine work that could be performed. I'm also intrigued by the 501(c)(3) option, though the 5-month timeline might be challenging if the need is urgent. The fiscal sponsorship approach while waiting for approval sounds promising. One question I have - for those who've successfully implemented any of these strategies, what kind of documentation did you find most important to maintain? I want to make sure everything is completely above board from day one. @Beatrice Marshall - your situation sounds really tough, and it's clear you genuinely want to help while being responsible about taxes. Whatever approach you choose, it sounds like getting official IRS guidance might be worth the investment given the amounts involved.

I just want to add that if you don't want to deal with the hassle of the ITIN application this year, you could file as "married filing separately" for now. Yes, you'll probably pay more in taxes, but it might be worth it if you need your return processed quickly. Then next year when you have more time, you can file jointly once your spouse has an ITIN or SSN. Just make sure you understand the limitations of MFS status - you lose several credits and deductions.

I went through this exact situation two years ago when I married my husband from the Philippines. Here's what worked for us: 1. Your spouse absolutely can get an ITIN - the W-7 form is still valid for spouses filing jointly. You'll need to check exception 1(d) on the form and write "Spouse of U.S. citizen/resident filing joint return" in the explanation section. 2. The tricky part is the documentation. You'll need either original documents (passport, birth certificate) or certified copies from the issuing agency (like the Philippine embassy in our case). Regular notarized copies won't work. 3. We attached the W-7 to our joint tax return and mailed everything together. The IRS processed the ITIN application first, then our return. Total time was about 10 weeks. 4. Pro tip: Double-check that your spouse qualifies as either a resident or non-resident alien for tax purposes, as this affects which exception category you select on the W-7. The IRS publication 519 has a good flowchart for this. The process is definitely still available despite what some outdated sources say. We successfully filed jointly and got our refund, just took patience with the timing. Good luck!

Has anyone actually been audited when using personal cards for business? All this advice sounds good in theory but I'm wondering about real experiences.

I've been using a personal card for my freelance business expenses for over two years now, and I can confirm what others have said - the IRS really doesn't care about the card type. During my recent interaction with a tax professional, they emphasized that the key is maintaining clear separation in your accounting records. What I've found helpful is using a dedicated personal card ONLY for business expenses, even though it's technically a personal card. This makes reconciliation much easier in QuickBooks and gives you a clear paper trail. I also keep a simple spreadsheet with business purpose notes for each transaction, which takes maybe 5 minutes per week but gives me peace of mind. The audit risk doesn't increase just because you're using a personal card - it increases if your expense patterns look unusual for your industry or if you can't properly document business purposes. As long as you're disciplined about record-keeping and only deducting legitimate business expenses, you should be fine regardless of card type.