How to properly claim medical expenses on taxes for maximum deduction?

Thanks for the detailed info. Quick question - can I include the premiums I pay for my health insurance through my employer as part of these medical expenses? Or is that handled differently because it comes out pre-tax from my paycheck? Also, if I paid for some alternative treatments like acupuncture for my chronic pain, can those count too?

Health insurance premiums paid through your employer with pre-tax dollars cannot be included in your medical expense deduction since you've already received a tax benefit. However, if you pay any portion of your premiums with after-tax dollars, that amount would be eligible. Acupuncture is absolutely deductible as a medical expense! The IRS recognizes acupuncture as a legitimate medical treatment. Other alternative treatments may also qualify if they're prescribed by a physician to treat a specific medical condition. Just make sure you keep documentation from your healthcare provider showing these were medically necessary treatments rather than simply for general wellness.

Does it integrate directly with TurboTax or do you have to manually enter the totals it gives you? I've got like a million receipts and EOBs from my insurance and honestly don't even know where to start.

How does it handle prescription medications? I have a ton of those expenses but some were covered partially by insurance and I'm confused about whether I claim the full amount or just what I paid out of pocket.

It doesn't directly integrate with TurboTax yet, but it gives you a complete summary report with all your deductible amounts organized exactly how you need to enter them in TurboTax. It seriously saved me hours of sorting through paperwork - you just snap pictures of everything or upload PDFs and it does the organizing for you. For prescription medications, it handles that perfectly - you only claim what you actually paid out of pocket after insurance. The system can even read your insurance EOBs and prescription receipts to determine the correct amounts automatically. It separates what insurance paid versus your actual expenses, which is exactly what you need for tax purposes.

Wait, I'm confused. Are you saying there's a service that can get you through to the IRS faster? How does that even work? I thought everyone has to wait in the same phone queue.

I'm extremely skeptical about this. Sounds like a scam to me. The IRS phone system is notoriously backed up - how could some random service possibly get you through faster than everyone else? What are they doing, paying off IRS agents? I'll stick with waiting on hold like everyone else.

It's not a separate line or anything shady like that. From what I understand, their system automatically navigates the IRS phone tree for you and stays on hold in your place. When a representative finally answers, you get an immediate call connecting you to that agent. So you're still using the normal IRS phone system, but you don't personally have to sit through hours of hold music. I was definitely skeptical too! But when I needed answers about some complicated medical expense questions for my mom's taxes, I was desperate. Was pleasantly surprised when it actually worked exactly as advertised. Not suggesting anyone needs to use it, just sharing what worked for me when I needed specific clarification on medical deductions.

Thanks for bringing this up! I'm in Minnesota and had no idea states might have different rules. Does anyone know if Minnesota has any special provisions for medical expenses? I'll look it up too, but thought someone here might know off-hand.

Minnesota does allow medical expense deductions, but they generally follow the federal rules. However, Minnesota has some specific provisions for certain care expenses that might help in your situation. If you're paying for long-term care services or have significant prescription drug costs, there are some additional state tax benefits you might qualify for. I'd definitely recommend looking at the Minnesota Department of Revenue website for details, as state tax provisions can change year to year. But in general, if you're itemizing medically on your federal return, those same deductions will carry over to your Minnesota return.

I switched from TurboTax to FreeTaxUSA last year and found it much better for handling my medical expenses. It's more straightforward about categorizing different types of medical costs, and I found their interview process more thorough for catching deductions TurboTax seemed to miss. Plus it's WAY cheaper. I was paying like $120 for TurboTax Deluxe plus state, and FreeTaxUSA was only about $15 for state (federal is free). Might be worth trying if you're not locked into the TurboTax ecosystem.

I've used H&R Block's software for the past three years, and it handles medical expenses pretty well. Their interface for entering medical expenses lets you categorize everything by type (doctor visits, hospital stays, prescriptions, etc.) which makes it easier to organize. One thing I really like is their audit risk assessment that gives you a heads-up if your medical deductions seem high compared to your income level. That helped me make sure I had all the proper documentation ready just in case.