Can someone explain how charitable donations tax write-offs work with standard deduction?

Does this mean there's literally no tax benefit at all for charitable giving unless you're rich enough to have deductions over the standard amount? That seems to discourage normal people from donating. Are there any strategies around this?

There are a few strategies that might help. One approach is "bunching" your donations - instead of giving annually, you could concentrate two or more years' worth of donations into a single tax year to exceed the standard deduction, then take the standard deduction in other years. Another option is a Donor-Advised Fund (DAF), which allows you to contribute a larger amount in one year for the tax deduction, then distribute those funds to charities over multiple years. Some people also explore Qualified Charitable Distributions (QCDs) from IRAs if they're over 70½, which can reduce taxable income directly. These strategies can help "regular people" still get tax benefits from charitable giving with some planning.

Does it work with non-cash donations too? Like I donate a lot of clothes and household items to Goodwill and always get those little receipts, but never know if I'm tracking them right or if it's even worth bothering.

I'm skeptical about these tax tools - how does it actually work? Does it just tell you things a regular tax preparer would, or does it actually do something special with charitable donations that H&R Block or TurboTax wouldn't?

It absolutely handles non-cash donations - that's actually one of its best features. You upload photos of your donation receipts and it helps value and categorize them properly, which is way more accurate than my manual guessing. It even flags when you might be undervaluing your non-cash donations, which is common. For your question about how it compares to other tax software - the main difference is it's focused specifically on planning rather than just filing. It analyzes multiple tax years together and shows you how strategies like donation bunching would change your actual bottom line across those years. Regular tax software mostly just processes the current year in isolation.

Wait, so this service just gets you through to an actual IRS person? How does that even work? I thought the whole problem was that the IRS doesn't have enough staff to answer calls...

Yeah right. Nothing gets you through to the IRS faster. I've tried calling them like 20 times about my refund and always get disconnected after waiting forever. Sounds like an ad to me.

It uses technology to navigate the IRS phone trees and waits on hold for you. When an agent actually picks up, it calls your phone and connects you directly to that live agent. It basically does the waiting for you so you don't have to sit there listening to hold music for hours. And about your skepticism - I totally get it. I was suspicious too, but I was desperate after trying to reach someone about my QCD question for weeks. The service really did connect me in about 12 minutes when I had previously waited over 2 hours before giving up. The IRS agent was surprised when I mentioned how I got through, but she still answered all my questions about charitable giving strategies.

How exactly does this work? Do you just transfer shares directly to the charity somehow? And do all charities accept stock donations or just the bigger ones?

You transfer the shares directly to the charity's brokerage account - most medium and large charities have a process for this. You'll need to contact their donation department for their specific instructions. They'll usually provide their broker info and account number. Many smaller charities can accept stock donations too, but some might not have the infrastructure. In those cases, there are donor-advised funds like at Fidelity or Schwab where you can donate the stock to the fund (getting the tax deduction immediately), then grant the money to any charity from there. The best part is you completely avoid the capital gains tax you would've paid if you sold the stock yourself, plus you still get the full market value as a deduction.

Technically those are deductible but practically not worth the hassle. You'd need receipts for everything, and most stores don't automatically provide them for these small donations. Plus, if you're taking the standard deduction anyway, they won't help your tax situation at all.