That's super helpful! I didn't realize I could estimate and amend later. I do have most of my insurance EOBs and could probably get the pharmacy summaries easily. Would bank statements showing payments to medical providers be acceptable if I can't get the detailed receipts?

Bank statements can be supporting documentation, but they're not ideal on their own since they don't show what the payment was specifically for. The IRS wants to know that the expenses were medically necessary and not for something like cosmetic procedures. Your best approach is to use the EOBs from your insurance company - they typically show both what was covered and what you paid out of pocket. Most insurance providers have online portals where you can download a full year's worth of statements. Also contact your pharmacies for medication summaries, which they can usually provide immediately. Between those two sources, you might account for 80-90% of your expenses without much hassle.

I second this! I have a chronic condition too and didn't realize I could deduct all the travel to specialists (400 miles round trip several times a year). Also deducted my CPAP supplies, air filter for allergies (with doctor's note), and even the portion of my utilities for the medical equipment. Added about $3k to my deduction!

Can you explain this with an example? I'm not sure I understand how the math works out.

Sure! Let's say you bought stock for $1,000 several years ago, and now it's worth $2,500. If you sold it, you'd pay capital gains tax on the $1,500 profit - which might be $225 if you're in the 15% capital gains bracket. Instead, if you donate that stock directly to charity, two things happen: First, you get a deduction for the full $2,500 current value (if you itemize). Second, you completely avoid paying the $225 in capital gains tax you would have owed if you sold it. So compared to selling the stock and donating cash, you save an extra $225 in taxes.

Unfortunately, that special provision expired. During the pandemic, the CARES Act allowed people to deduct up to $300 ($600 for married couples) in charitable donations without itemizing. But that was temporary and is no longer available for current tax years. For 2025, you'll need to itemize deductions to get any tax benefit from charitable giving. That said, it's always worth checking for new tax laws as we get closer to filing season, as Congress occasionally introduces new provisions.

Where do you find old returns in FreeTaxUSA? I've been using them for years but never figured out how to see my past filings.

You need to log into your FreeTaxUSA account, and on the main dashboard there should be a section called "Prior Year Returns" or "Tax Return History." Click on that and you'll see all the years you've filed with them. Select 2019, and you can view or download the full PDF of that return. If you downloaded and saved your returns each year, you can also just open the PDF directly from your computer. The Schedule A is usually around page 11-13 of the complete return.

States are required to issue 1099-Gs for all refunds they send, but sometimes they don't if the amount is very small. $340 is actually right around the threshold where some states might not bother. Technically you're still supposed to report it if you itemized that year, but realistically the tax impact would be very minimal.

No penalty if the IRS owes YOU money! But your cousin only has 3 years to claim that refund or she loses it forever. So she has until April 2027 to file her 2023 return and get that money back. The IRS is totally happy to keep your refund if you don't ask for it back in time!

She did start college in fall 2023, so this is really good to know. We paid about $3,500 out of pocket after her scholarships. I'll make sure we look into that credit when filing her prior year tax return. Thank you!

That's really good advice. I think I have most of my contribution records in old emails, but should I also request official documentation from my financial institution to be safe?

Absolutely get official documentation if you can. Year-end statements are great because they often summarize annual contributions. Some institutions also provide specific tax forms or contribution confirmations. If they offer any kind of contribution history report, definitely request that. Email confirmations are good supplementary evidence, but official statements directly from the institution carry more weight if there's ever a question. The more documentation you have, the better, especially for older contributions that might be harder to verify years later.

I tried that with Vanguard last year and they refused to change the code. They said their policy is to use code 1 for all early distributions and it's up to the taxpayer to claim any exceptions on their tax return. Super annoying but apparently common practice.