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!

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.

I've been following Jackson Hewitt processing times closely this season, and what you're experiencing is unfortunately very common right now. JH seems to have had significant backend issues with their submission process, particularly affecting returns with any complexity (marriage status changes, credits, etc.). From what I've observed, their March filings are taking 25-30 days on average versus the typical 21. The fact that you're newly married filing jointly adds another layer of IRS verification that can extend processing. I'd recommend checking your IRS transcript directly rather than relying solely on WMR - it often shows movement days before the Where's My Refund tool updates. If you're past the 21-day mark, you can also call the IRS practitioner hotline, though wait times are brutal right now. Don't panic yet - delays don't necessarily indicate problems, just volume and verification backlogs.

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!

Quick tip for anyone dealing with these verification letters - if you need multiple copies for different schools or applications, you can request additional copies through the IRS online account portal or by calling that 800 number. They'll send you official copies with the same tracking ID. Super helpful if you're applying to multiple schools or programs that each need their own copy! Also, these letters are typically valid for about 120 days from the issue date, so if you're planning to use it for next year's FAFSA or other applications, just keep that timeline in mind. The February 15th date on yours gives you plenty of time though! Hope this helps other folks who might be in similar situations 😊

Just wanted to chime in as someone who works in financial aid - this is totally normal! When students submit their FAFSA and indicate they won't be filing taxes (or haven't filed yet), we often automatically request these verification letters on their behalf. The Memphis processing center handles a ton of these requests, especially during FAFSA season (January-March). The fact that you got this in mid-February with that tracking ID suggests it was likely requested as part of your financial aid verification process. Schools need official documentation from the IRS to confirm non-filing status - it's a federal requirement. You're all set for your FAFSA! Just make sure to submit this letter to your school's financial aid office if they haven't received it directly. And like others mentioned, definitely keep copies for your records. These letters are gold for students who don't have tax returns to submit! 📚💰

Gabriel, I went through this exact same confusion when I formed my LLC and elected S Corp status! The good news is that based on what you've described, you're likely still within your filing window. The 2 month and 15 day period starts from the earliest of three events: when you begin conducting business, when you acquire assets, or when you issue stock. Simply having your Articles of Incorporation filed doesn't automatically start the clock - it's about when you actually start operating as a business. Since you mentioned you haven't opened business bank accounts or conducted any transactions yet, your deadline period may not have even begun. The key is documenting when you take your first actual business action (opening that business bank account, making your first purchase, issuing stock certificates, etc.). I'd recommend filing Form 2553 as soon as you do start business operations, rather than waiting until near the deadline. And definitely keep detailed records of when you begin each business activity - this documentation will be valuable if the IRS ever questions your timeline. Don't stress too much about this! The IRS understands that new business owners often face confusion about these deadlines, and they're generally reasonable about late election relief if needed. But it sounds like you may not even need that option.

Gabriel, you're getting great advice here! I want to add one important point that might help clarify your situation even further. The IRS specifically states that for new corporations, the election period begins when the corporation first has shareholders, acquires assets, or begins doing business - whichever occurs first. Just having your Articles of Incorporation filed is considered "existing" but not necessarily "doing business." Since you got your EIN on 2/28/24 but haven't mentioned opening business bank accounts, issuing stock certificates, or conducting any actual business transactions, you're likely still in a pre-operational phase. This means your 2 month and 15 day window hasn't started yet. One practical tip: when you do open your business bank account or take your first business action, immediately put a reminder in your calendar for 75 days later (2 months + 15 days) to ensure you don't miss your Form 2553 deadline. And consider filing the form within the first 30 days of starting operations rather than waiting until the deadline approaches. You're being smart to research this thoroughly upfront rather than discovering the deadline after it's passed. Many new business owners aren't even aware of the S Corp election option until it's too late!