Money Moves for CRNAs

Can the IRS really deny a legitimate deduction? Yes—and it happens more than you think.

In this episode of Money Moves for CRNAs, we break down a real 2025 Tax Court case where a taxpayer lost a $6,700 charitable deduction… not because it wasn’t valid—but because the documentation didn’t meet IRS standards.

And here’s the problem: Most 1099 CRNAs are making the exact same mistake.

We cover:
  • Why the IRS denied the entire deduction (not just part of it)
  • The critical documentation rules most people miss
  • What Form 8283 actually requires
  • Why Goodwill receipts often aren’t enough
  • How to properly document donations before filing your return
If you’re a 1099 CRNA trying to maximize deductions while staying audit-proof, this episode will show you exactly where the risks are—and how to fix them.

Key takeaway: Good intentions don’t protect deductions. Documentation does.

Chapters:
00:30 – The $6,700 deduction the IRS denied
01:20 – What the taxpayer did wrong (critical mistake)
02:00 – IRS substantiation rules explained
02:30  – The Goodwill receipt trap
03:00 – Why you can’t fix documentation later
03:42 – What 1099 CRNAs should do instead
04:35 – Final takeaway: documentation vs intention

Music licensed from PremiumBeat.com under License #7394047

What is Money Moves for CRNAs?

Twice a month, get clear, smart tips to help you keep more money, build wealth, and make taxes easier for 1099 CRNAs.

Bill White:
Welcome to Money Moves for CRNAs—the podcast created specifically for 1099 CRNAs who want clarity, confidence, and control over their money.

This podcast is for educational purposes only, and is not personalized tax or financial advice.
Here’s your host, Randy Larkin, with Atlanta Tax Planner…

Randy Larkin:
Alright—

Let me give you a quick story from a recent Tax Court case that came out July 2025…and frankly, this has been widely misunderstood during this past tax season.

A taxpayer donated about $6,700 worth of clothing and household items to charity. Pretty normal, right?

Dropped it off… got a receipt… claimed the deduction.

And the IRS denied the entire thing.

Not part of it— all of it.

Now here’s what’s important…

The IRS didn’t say the donation wasn’t real. They didn’t argue about the value. They denied it purely over documentation.

That’s it. So what went wrong?

The taxpayer filed Form 8283, listed the charities, included general descriptions— but missed some key details: No donation dates. No values listed.

And the receipts from the charities didn’t describe the actual items.

So when the IRS reviewed it, they said: not good enough.

He tried to fix it later— basically, reconstructing records after the fact.

And the court said something very clear: Too late.

And denied the full deduction.

Now here’s where this matters for you as a 1099 CRNA…

There are very specific substantiation rules for charitable contributions, and they get stricter as the dollar amount goes up.

Over $250—you need a contemporaneous written acknowledgment
Over $500—you need detailed records: how you got the items, what they cost
Over $5,000—you may need a qualified appraisal

But here’s the part most people miss…

That Goodwill receipt you get? The one that says “miscellaneous household items”?

That’s usually not enough.

And this is the trap.

Because most people think: “I donated it, I got a receipt, I’m covered.”

But the IRS says no— you need itemized documentation, and it has to be done before you file your return.

You don’t get to fix it later.

Not during an audit. Not after the fact.

Once that window closes, the deduction is gone.

And this is exactly why we spend time staying on top of recent Tax Court cases like this.

Because these aren’t theoretical rules— they’re real decisions that show how the IRS is enforcing things right now.

Most CRNAs don’t have time to read Tax Court opinions… and you shouldn’t have to.
We do that, we track these cases, interpret them, and translate them into what actually matters for your situation.

So what should you do instead?

Keep it simple— but be proactive: Create a detailed list of what you’re donating— descriptions, estimated values, and ideally original cost.

Take photos, especially for higher-value items.

Give that list to the charity at the time of donation.

And have them sign off on it.

And keep everything together with your tax records.

Because at the end of the day, the responsibility falls on you— not the charity.

And this is something we go deeper on inside our CRNA Learning Center, we break down strategies and real-world cases, specifically for 1099 CRNAs.

Because applying generic tax advice to a CRNA income model doesn’t work very well.

So the takeaway is simple:

Even legitimate deductions can be denied if the documentation isn’t right.

And the IRS is not flexible on this.

Good intentions don’t save deductions.

Documentation does.

Bill White:
Thanks for listening to Money Moves for CRNAs. New episodes drop twice a month. See you soon.