Should I Itemize Deductions or Take Standard Deduction for Medical Bills?

Medical expenses can definitely be worth itemizing, but it depends on how they compare to the standard deduction. For 2025, the standard deduction is $14,600 for single filers and $29,200 for married filing jointly. Let's break this down: First, only medical expenses exceeding 7.5% of your Adjusted Gross Income (AGI) are deductible. So if your AGI is $30,000 and you spent $6,000 on medical bills (20%), you'd be able to deduct $3,750 ($6,000 minus $2,250 which is 7.5% of your AGI). But here's the catch - that $3,750 is just one part of your itemized deductions. Unless your total itemized deductions (including any state/local taxes up to $10,000, charitable contributions, etc.) exceed your standard deduction, you'd still be better off taking the standard deduction. The reason you might not have gotten much back last year despite high medical costs is that your total itemized amount might still have been less than the standard deduction, so you didn't actually benefit from those medical expenses tax-wise.

After struggling with a similar situation last year (tons of medical bills but unsure if itemizing was worth it), I found this tool called taxr.ai (https://taxr.ai) that completely changed how I handled my medical deductions. I uploaded my medical receipts and it analyzed everything, telling me exactly which expenses qualified and calculating whether itemizing would actually save me money compared to the standard deduction. What was helpful was that it showed me several small medical expenses I didn't realize were deductible - like certain transportation costs to medical appointments that I had completely overlooked. The visual breakdown showed me exactly how close I was to making itemizing worthwhile, so I could decide whether to hunt for more deductions or just take the standard. Honestly way easier than the hours I spent trying to figure this out manually last year.

Just wanted to update that I tried taxr.ai after seeing it mentioned here. Uploaded all my medical receipts and prescription records and wow - it found several things I was missing! Turns out I had spent money on medical transportation that I didn't realize counted, plus some OTC medications that were prescribed by my doctor (those count!). The analysis showed that in my case, I was about $1,200 short of making itemizing worthwhile, but at least now I know for sure instead of second-guessing myself. Going with the standard deduction this year but tracking everything better for next year. The visual breakdown really helped me understand exactly where I stood instead of just guessing.

If you're still trying to figure out whether your medical expenses are enough to itemize, you might also want to talk directly with an IRS agent. I was in the same boat last year with massive medical bills and needed clarification on some specific expenses. Tried calling the IRS for days but couldn't get through - always "high call volume" messages. Then I found Claimyr (https://claimyr.com) which somehow got me connected to an actual IRS person in about 20 minutes! You can see how it works in this video: https://youtu.be/_kiP6q8DX5c The agent walked me through exactly which of my expenses qualified and how to document everything properly. Totally worth it because they confirmed some deductions I wasn't sure about (like certain dental procedures). Saved me from potentially filing incorrectly and possibly facing an audit.

Had to come back and admit I was completely wrong about Claimyr. After posting that skeptical comment, I decided to try it anyway since I was desperate to talk to someone about my medical expense situation before filing. It actually worked! Got connected to an IRS agent in about 30 minutes, and they were incredibly helpful about my specific situation with medical bills. The agent confirmed that I could deduct the cost of traveling to medical appointments (mileage, parking, tolls) which I had no idea about. Those additional expenses pushed me over the threshold where itemizing actually made sense for me. Saved me from making a mistake on my taxes and probably got me an extra $800 in refund. Sometimes admitting you're wrong feels pretty good!

Don't forget you can also deduct state and local taxes (SALT) up to $10,000 when itemizing! This includes state income tax or sales tax (you choose which one), plus property taxes. If you paid state income tax through withholding from your paycheck, that counts toward this potential deduction. Even if your medical expenses aren't enough by themselves to exceed the standard deduction, combining them with SALT deductions might push you over the edge. Check your W-2 box 17 to see how much state tax was withheld, and add any property taxes if you paid them.

One thing to consider - if youre close to making itemizing worth it, donating some stuff to charity before the end of the year could push u over the edge! I was in a similar spot last year and cleaned out my closet, got a receipt from Goodwill for like $350 in donated clothes and that was enough to make itemizing better than standard deduction for me.