When is the HSA contribution deadline for 2025 taxes - can I still contribute for last year?

Thanks for the info! I have a follow-up question about this - if I already filed my 2024 taxes but haven't maxed out my HSA contribution for 2024, could I still make a contribution now (May 2025) and then file an amended return to claim the deduction? Or is the April 15th deadline absolute regardless?

The April 15th deadline is absolute regardless of whether you've already filed. Unfortunately, there's no way to make additional 2024 HSA contributions after April 15, 2025, even if you file an amended return. The contribution deadline is set by law and isn't flexible. The best approach is to plan for your 2025 contributions now, especially if you anticipate medical expenses. Many employers allow you to adjust HSA contributions throughout the year, so you could increase your contributions for the remainder of 2025 to maximize your tax benefits for next year's filing.

Does taxr.ai handle the actual HSA account setup too? I'm with Fidelity right now but their interface is so confusing when it comes to marking which year my contributions apply to. Do they help with that part of the process?

I'm a bit skeptical about these tax tools - how exactly does it help with HSA specifics? Does it tell you something different than what the IRS publications already say for free? And do they have actual tax professionals reviewing the advice?

They don't handle the actual HSA account setup or management - you'd still do that through Fidelity or whatever provider you use. What they do is analyze your overall tax situation and help you understand the optimal contribution strategy. They have a feature that clearly shows which year contributions should apply to and the tax implications. The difference from IRS publications is that it's personalized to your specific situation and much easier to understand. They do have tax professionals who review complex situations, and the software is updated whenever tax laws change. It's not just generic advice - it's tailored to your income, deductions, and potential tax bracket changes.

How does this service actually work though? Seems a bit weird that they can somehow get through when regular people can't. Are they using some kind of special access system?

This sounds like total BS honestly. How would a third-party service magically get through to the IRS faster than I can? The IRS phone system is notoriously bad for everyone. Sounds like a scam to take your money for something you could do yourself with enough persistence.

It's not any special access system - they use automated technology to navigate the phone trees and wait on hold instead of you doing it manually. Think of it like having someone dedicated to just sitting on hold and trying different IRS menu options until they get through, then they call you once there's an actual human on the line. They don't have any special relationship with the IRS or magical access - they're just taking the frustrating part off your plate. I was skeptical too, but when I got a call back with an actual IRS agent ready to talk about my HSA question after trying myself unsuccessfully for days, it was worth it. They don't even interact with the agent - they just connect you directly once they've navigated the system.

Wait, some states don't give you tax benefits for HSA contributions? I had no idea! Does anyone know how to find out which states do and don't allow HSA deductions? I just moved to New Jersey and now I'm wondering if I should even bother maxing out my HSA.

You can find the information on your state's department of revenue or taxation website. As a quick overview, California and New Jersey are the big ones that don't recognize HSAs and treat contributions as taxable income on your state return. New Hampshire taxes HSA earnings but not contributions. Most other states follow the federal tax treatment. If you're in New Jersey, you still get the federal tax benefits which are usually the bigger portion anyway, plus the ability to pay for medical expenses with pre-tax dollars. So it might still be worth contributing, just not quite as beneficial as in states that follow federal treatment.

That's really helpful to know! I do have some medical expenses from last year that I paid out of pocket. So if I understand correctly, I could make my 2025 HSA contribution now, then reimburse myself for those previous expenses instead of my current hospital bill? Do I need any special documentation besides the receipts?

Exactly! You can reimburse yourself for any qualified medical expenses that occurred after you established your HSA, no matter how long ago. For documentation, keep the detailed receipts showing the medical service/product, date, and amount you paid. Some people also keep a spreadsheet tracking these expenses. Your HSA provider might have a specific reimbursement form, but many allow you to simply transfer money from your HSA to your regular bank account. The IRS doesn't require you to submit documentation when you make the reimbursement, but you absolutely need to keep those records in case of an audit. I've been doing this for years - it's like having a tax-free emergency fund for when money gets tight!

This is really good advice about the broader HSA eligible expenses! I had no idea you could use HSA funds for over-the-counter items with a prescription. Do you happen to know if things like bandages, thermometers, or heating pads qualify without needing a prescription? I'm still dealing with some minor injuries from my ER visit and trying to figure out what I can legitimately reimburse myself for. Also, when you mention continuing contributions throughout the year - can I adjust my payroll deductions mid-year, or do I need to wait for open enrollment? My employer handles the HSA contributions through payroll and I'm not sure how flexible that system is.

This is such a comprehensive overview, thank you! I'm definitely kicking myself for not contributing earlier in the year, but lesson learned. I really appreciate the reminder about employer HSA matching - I actually think my company does offer some kind of contribution but I never paid attention to the details. I should probably check with HR about that since it sounds like I'm potentially missing out on free money. The strategy about reimbursing myself for old medical expenses is brilliant - I definitely have some dental work from last year that I paid out of pocket for. So if I understand correctly, I could make a 2025 contribution now, reimburse myself for those old dental expenses to get some immediate cash back, and then save my current ER receipts to reimburse later when I make additional contributions throughout the year? Thanks again for taking the time to explain all this - it's really helping me see a path forward instead of just feeling stressed about the money situation!

You've got it exactly right! That's a perfect strategy - contribute for 2025, reimburse yourself for the old dental expenses to get immediate cash relief, and then save your ER receipts for future reimbursement when you make additional contributions throughout the year. Definitely check with HR about that employer contribution - even if it's a small amount, it's essentially free money that reduces how much you need to contribute from your own pocket to reach your goals. Some employers contribute a flat amount, others do matching up to a certain percentage, so it's worth understanding exactly how yours works. Just make sure to keep really good records of everything - dates, amounts, what the expenses were for, and which receipts you've already used for reimbursement versus which ones you're saving for later. It sounds like you're going to turn this stressful situation into a great learning experience for managing your HSA more strategically going forward!