Could you potentially categorize these expenses differently? Instead of withdrawing from your HSA, could you give your girlfriend the money personally, and then she pays for the medical expenses? That way they're being paid by the person who claims the child as a dependent. I realize it's more steps, but might avoid any potential HSA compliance issues.

Thanks everyone for the detailed responses! This has been really helpful in understanding the complexity of HSA rules for non-traditional families. Based on what I'm reading, it sounds like I have a few options to consider: 1. Keep the current arrangement where my girlfriend claims her son, and I just give her the money to pay medical expenses directly (thanks @Annabel Kimball for that suggestion) 2. Explore the "local parent" option that @PaulineW mentioned, since I do provide more than half his support when you include housing, insurance, and daily expenses 3. Get official clarification from the IRS using one of the services mentioned here I think I'm leaning toward option 1 for now since it's the simplest and avoids any potential compliance issues. The $1,200 medical bill isn't worth risking penalties over. But for future planning, I might look into whether it makes sense for us to switch who claims him as a dependent. We'd need to run the numbers on both scenarios to see what works better for our household overall. Really appreciate everyone taking the time to explain these rules - HSA dependency requirements are way more complicated than I realized!

Jackson Hewitt is having delays this year. I work at a bank and we're seeing a pattern with tax prep services. Most DIY filers (TurboTax, FreeTaxUSA) are getting processed in 2-3 weeks. Professional preparation services like JH and H&R Block are taking 3-5 weeks right now. IRS is prioritizing simple returns first. If you're newly married with any credits or deductions, that puts you in a more complex category.

I filed through Jackson Hewitt on February 20th and I'm in the exact same situation! Also newly married and filing jointly for the first time. My WMR has been stuck on "processing" for weeks now. After reading through all these responses, it sounds like JH has definitely had some system issues this year, especially with more complex returns like ours. I'm going to check my transcript like Connor suggested - didn't even know that was a thing! It's somewhat reassuring to know we're not alone in this delay, though I wish JH had been more upfront about the processing issues they were having.

dont forget to make copies before you send it anywhere! learned that one the hard way lol

Just want to add - if you're worried about identity theft or someone requesting this without your permission, you can always call that 800-829-1040 number to verify. They can tell you who made the request and when. Better safe than sorry, especially with all the tax scams going around these days. But sounds like you needed it for FAFSA anyway so you're all set! 👍

Another thing to consider - if your mom owns her home, she might be eligible for property tax relief or homestead credits in many states. These often require filing a state tax return even when federal filing isn't required. Also, has she been paying estimated taxes during these unfiled years? If not, and she does end up owing, you might want to look into the IRS Fresh Start program which can help with penalties.

I'm going through something very similar with my grandmother right now, so I completely understand the stress and worry you're feeling! One thing that really helped us was getting organized first before diving into the actual filing process. Here's what we did: First, we gathered all her income documents for each year (SSA-1099s, 1099-Rs, 1099-INTs, etc.) and made separate folders for 2021, 2022, and 2023. Then we collected all those IRS notices and sorted them by date to see what they were actually asking for. The biggest relief was discovering that many of the "scary" notices were just automated reminders, not actual threats. Some were even for years she didn't need to file at all! Since your mom's income situation sounds relatively straightforward (Social Security + pension + small interest), this might be manageable to tackle together. But honestly, given that she's been getting IRS correspondence for a while, it might be worth the peace of mind to consult with a tax professional who specializes in unfiled returns. They can quickly determine which years actually require filing and help navigate any correspondence with the IRS. The most important thing is that you're helping her address this now - ignoring it only makes things more complicated. You're being a great child by stepping in to help sort this out!

I made a mistake with my S Corp election timing and had to file for late election relief. Here's what worked: File Form 2553 ASAP and attach a statement explaining why you missed the deadline (be specific about the reasonable cause - like confusion about when the deadline applied, lack of knowledge about the requirement, reliance on incorrect advice, etc.) The IRS is actually pretty lenient with new business owners who have reasonable cause. Just make sure everyone who owns stock signs the form and you check the box for late election.

Gabriel, based on your situation, you might still be within your filing window! Since you incorporated on 1/15/24 but haven't mentioned actually conducting business activities yet, the 2 month and 15 day period may not have even started. The key is when you first conducted business, acquired assets, or issued stock - not just when your Articles were filed. If all you have are the Articles and EIN with no actual business activity (no bank account opened, no transactions, no stock issued), then your deadline clock hasn't started ticking yet. When you do start your first business activities, you'll have until 2 months and 15 days from that date to file Form 2553. This gives you much more flexibility than the March 15th deadline you were worried about. Just make sure to document exactly when you begin business operations so you have a clear record of your deadline. And file Form 2553 promptly once you do start - don't wait until the last minute!