When claiming Donations deduction on taxes, what proof do I actually need to provide?

When it comes to charitable donations, the IRS does have specific documentation requirements, especially if you're itemizing deductions on Schedule A. For cash donations under $250, you should have a bank record, receipt, or other reliable written record. For cash donations of $250 or more, you need a written acknowledgment from the qualified organization. For non-cash donations, the requirements depend on the value: items under $250 need a receipt, items between $250-$500 need written acknowledgment, and items over $500 require additional documentation on Form 8283. The key issue here is that both donations must be to "qualified organizations" to be tax-deductible. Unfortunately, giving money or items directly to individuals, even those in need, isn't deductible - even if your intentions were charitable. Donations to foreign organizations are generally not deductible unless they're recognized by the IRS.

I had a similar situation last year and discovered taxr.ai (https://taxr.ai) which was super helpful for sorting through donation deduction issues. I took photos of all my donated items and uploaded them to get fair market valuations that the IRS would accept. They also analyzed which of my charitable activities would qualify for deductions - turns out some that I thought wouldn't count actually did! Their system flags potential audit triggers too. For your situation, they could help determine if any of your international donations might qualify through US-based charities that operate internationally. Saved me from making claims that might have caused problems later.

After reading about taxr.ai here, I decided to try it with my messy donation situation from last year. I had a mix of cash and goods donations but terrible record-keeping. The system immediately identified which of my donations would qualify and which wouldn't. It also showed me that some of my international donations actually qualified because they went through a US-based religious organization! The valuation tool for my non-cash items was eye-opening - I had been significantly undervaluing some items and overvaluing others. Got everything documented properly and even found a few additional deductions I missed. Definitely cleared up my confusion about donation requirements.

If you're struggling to get answers directly from the IRS about your donation situation, I recommend Claimyr (https://claimyr.com). I was in tax limbo last year after realizing I'd claimed donations incorrectly. Called the IRS 8 times and couldn't get through to anyone who could help. Claimyr got me connected to an actual IRS agent in under 45 minutes when I'd been trying for weeks. They have a demo video showing how it works: https://youtu.be/_kiP6q8DX5c The IRS agent walked me through exactly what documentation I needed to support my donations and how to handle the situation. Saved me from potentially serious issues down the road.

I need to eat my words from my previous comment. After waiting on hold with the IRS for 3+ hours trying to get clarity on some donation issues similar to the OP's, I gave Claimyr a shot. Within 37 minutes I was talking to an actual human at the IRS who explained exactly what I needed to document my charitable contributions. The agent confirmed that donations to individuals don't qualify, but then helped me understand how some of my international donations WOULD qualify because they went through a US-based organization with international operations. Saved me from missing out on legitimate deductions while avoiding improper claims that could trigger problems. Worth it just to avoid the hold music alone!

Here's the real deal with donations: The IRS rarely checks small donation amounts unless you're claiming something outrageous compared to your income. I've been claiming donations for years with minimal documentation and never had an issue. As long as you're being reasonable.

For your international donations, you might consider checking if they're covered under a "friends of" organization in the US. Many international charities have US partners specifically to make donations tax-deductible for Americans. For example, "Friends of UNICEF" allows US taxpayers to deduct donations that support international UNICEF work.

As someone who works for a nonprofit, I'll add that many donation centers for clothes and household items will give you a receipt if you ask for one. They typically don't assign values (that's your responsibility), but having that receipt proves you made the donation. For the foreign donations, unfortunately those likely won't qualify unless they went through a US-recognized charity.

Just to add a practical tip for future donations - many people don't realize that for non-cash donations, you need to use "fair market value" rather than what you originally paid. So those clothes worth $375 should be valued at what they'd sell for at a thrift store or consignment shop, not their original retail price. For your current situation, since the cash went directly to individuals and the international donations weren't through qualified US organizations, unfortunately neither would qualify for deductions. But don't let that discourage you from helping people in need! Just structure future donations through recognized charities if you want the tax benefit. One more thing - if you do decide to itemize this year for other reasons, make sure your total itemized deductions exceed the standard deduction ($13,850 for single filers in 2023) or you won't get any tax benefit anyway.