1. Who should I be asking to obtain the cash donation receipt if the cash donations are to random buckets at checkout stands, Ronald McDonald House at drive-thru, Good Will buckets, etc...
2. How "official" does the receipt have to be? On letterhead? Can it be handwritten?
The details are not clear as to what exactly is needed for cash donations. I understand if it's a church or school, that's easy to get, but some cash donations are not that simple.
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You will likely lose those donations if audited, there is not much way around it. The alternative is not to put loose cash into a counter-top cash box at Mcdonalds, for example, but to mail a check to the RM house or make an electronic donation online.
For all donations you are required to have a bank record. This can be a credit card statement or canceled check. The recipient is only required to issue a receipt if the donation is more than $250, or more than $75 if the transaction is partly a donation and partly for a service. (Like tickets to a charity dinner where you have to account for the value of the dinner).
The receipt has to be from the recipient organization. That would normally require an authorized person. That doesn't have to be a high official -- the kid at the back door of Goodwill issues receipts when you bring in your old household stuff, so is probably authorized. But I doubt that counter employees of one company who have custody of a cash box or donation bucket for a third party organization would be authorized to issue a receipt if you asked, and I doubt it would be accepted as valid. (The kid at McDonalds is not a representative of RM House and probably can't issue a legal receipt in their name.)
If this is a problem you can simply change your pattern of donation, make online gifts with electronic records instead of cash gifts into anonymous cash boxes.
Also, since the standard deduction is doubled with tax reform, many fewer taxpayers will have enough deductions to be worth itemizing.
The regulation says "record" not "receipt" for small amounts. The regulation further defines what needs to be part of that "record." (Who, amount, date, etc...) In fact, I made a call to the IRS myself about "money you put in a bucket at Salvation Army." If I know the EXACT amount of the change, and I make an entry into Quicken (or some type of computer software), would it be accepted? The agent hemmed and hawed.... and then said, "Depends whether or not you p*** off the Auditor...."
Bottom line, small amounts (under $250) do NOT require a "Receipt," just a "record." Make sure you have some type of "record" even if it's just a spreadsheet.
Page 17 bottom middle column (of the 2017 version of Pub 526at the bottom says, "you must keep RECORDS...." The kinds of records to keep depends on the amount of the contribution.
Then it goes on to define "cash" contributions and says "generally... you can't deduct a cash contribution regardless of the amount unless you have... (blah blah blah.....). This conflicts with the "you must keep records" part.
As long as you have a carefully kept "record" of some sort of your cash contributions showing the amount, date, who, and what purpose, for SMALL amounts, you MIGHT be able to pass muster. I do it all the time, but I'm an accounting nerd.
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