Wife filed using standard deduction but I need to itemize - can I still do this?

You're correct that when married filing separately, if one spouse itemizes deductions, the other spouse must also itemize - even if the standard deduction would be more beneficial. Since your wife already filed using the standard deduction, you technically have three options: First, you could file using the standard deduction too, which means giving up the tax benefit of your medical expenses and charitable donations. Second, you could file using married filing jointly, combining both your incomes and deductions on one return. Third, your wife could file an amended return (Form 1040-X) to switch to itemized deductions, and then you could file your return with itemized deductions. Given your significant medical expenses and charitable contributions, the amendment route might make the most sense financially, even though it's a bit of a hassle.

Had a similar headache last year and found this service called taxr.ai (https://taxr.ai) that really helped me figure out the best approach. I uploaded our tax documents and it analyzed everything to show us the difference between amending vs. filing jointly vs. both using standard. It showed us exactly how much we'd save by having my wife amend her return to itemize vs. the other options. The analysis saved us almost $3,200 because it turned out amending was WAY better than sticking with standard in our case with our medical bills.

Just wanted to follow up - I tried taxr.ai after posting my skeptical comment. I gotta say it was actually really helpful! I uploaded our returns and it showed that my wife amending would save us about $2,400 compared to both taking standard deduction. The breakdown of medical expense thresholds was super clear and it even factored in the amendment filing costs. We're going with the amendment route now and I'm way less stressed about the whole situation. It also confirmed what I suspected - that in our case, filing separately still beats filing jointly because of my income-based repayment plan, even with the itemization issue.

If you need to contact the IRS about how to handle this (which I recommend), use Claimyr (https://claimyr.com) to get through to an agent. I spent DAYS trying to get someone on the phone about an amendment issue last year and kept getting disconnected. Found their service through a YouTube video (https://youtu.be/_kiP6q8DX5c) and got connected to an IRS agent in about 20 minutes. The agent confirmed exactly what I needed to do with my MFS amendment and gave me specific instructions on how to note everything so both returns would be processed correctly. Totally worth it to get definitive answers straight from the IRS rather than guessing.

OMG, I'm eating my words about Claimyr being a scam. After my skeptical comment, I decided to try it today out of desperation. Got connected to an IRS agent in 25 minutes who was incredibly helpful! They confirmed that my wife should file Form 1040-X to amend her return to itemized deductions, and explained exactly what documentation we'd need. The agent even gave me helpful tips about tracking the amendment status and said that the processing time is currently running about 16 weeks, but that I shouldn't wait to file my return with the itemized deductions. They also told me to include a note referencing my wife's amendment in process. Never would have gotten this clarity without actually speaking to someone!

Just wanted to add something important that nobody's mentioned yet - make sure you consider the state tax implications too! Depending on your state, the rules about standard vs. itemized deductions might be different than federal. In my state, you're not required to match your federal filing choice. So when my spouse and I were in this exact situation (he filed standard, I needed to itemize), I was able to itemize on federal and take the standard deduction on state, which was the best of both worlds for our situation.

Have you considered filing for an extension? This would give you more time to figure this out. The extension gives you until October to file (though you still have to pay any estimated taxes owed by the original deadline). My husband and I were in a similar situation last year with medical expenses and it gave us enough time to really evaluate both options and speak with a tax professional.

I went through this exact same situation two years ago and it was such a headache! My wife had already filed with standard deduction and I realized I had over $15K in medical expenses that would put me way over the standard deduction threshold. What we ended up doing was having her file an amended return (Form 1040-X) to switch to itemized deductions. Yes, it was a pain and took about 12 weeks to process, but we saved over $4,000 in taxes so it was absolutely worth it. The key thing is to make sure you keep really good documentation of everything - all your medical receipts, charitable donation receipts, etc. One tip that our tax preparer gave us: when you file your return with itemized deductions, include a brief note explaining that your spouse is amending her return to also itemize. This helps prevent any confusion if the IRS processes your returns at different times. Also double-check your medical expense threshold calculation - remember that medical expenses are only deductible to the extent they exceed 7.5% of your adjusted gross income. With $18,500 in medical expenses, you should definitely clear that hurdle though!

I'm dealing with a very similar situation right now! My spouse filed with standard deduction in February and I just discovered I have significant business expenses and charitable donations that would make itemizing much more beneficial. One thing I learned from my tax preparer is that you should calculate the exact savings before deciding to go through the amendment process. With your $18,500 in medical expenses and $7,200 in charitable donations, you're looking at potentially substantial savings, but make sure to factor in the 7.5% AGI threshold for medical expenses like Josef mentioned. Also, if you do decide to have your wife amend, I'd recommend using a tax professional rather than trying to navigate Form 1040-X yourself. The amendment process can be tricky, especially when it involves switching from standard to itemized deductions, and having professional help ensures everything is done correctly to avoid delays or complications. The good news is that even though it's a hassle, you're not stuck with the standard deduction if the numbers work out better with itemizing. Just make sure to keep detailed records of everything and be prepared for the longer processing time.