Non-cash contributions ordered in 2025, shipped by vendor on several dates in 2026. Which year, and do I need to itemize each date?

[nystaxpayer12]

On 12/31/2025, I ordered several identical new items from a charity "wish list" to be shipped directly to the charity by the large, well-known online vendor. For some reason, the order for my relatively modest requested quantity went through and I was not told there was a supply issue, or I would have made different choices.  I just discovered that the vendor charged and shipped one or two items at a time on several dates in January and February.

Usually, I know that last-minute cash/credit card contributions are deductible in the year made and in past years, I have completed Form 8283 for gifts in kind like this with the assumption that if bought in one year and shipped reasonably promptly in early January, I could deduct in the year of purchase. Now I don't know. My order receipt with the total cost for all items is 2025, but I have all these small charges in 2026. Do I need to wait until next year for 2026 deductions, and do I need to itemize every date? There is not enough space on one Form 8283 if so. Thank you in advance.

[Opus 17]

For IRS purposes, the donation or purchase is made when the money leaves your control and is no longer cancellable or retrievable.  If the entire purchase was finalized on 12/31 and you could not have canceled the delayed items, then it would be a 2025 donation, even though the charity did not receive the items until 2026.  However, if parts of the order were cancelable by you (even if you didn't realize it), then those portions were not donated until 2026. 

[Mike9241]

2026 because the items weren't sent until that year. If $250-$500, the Charity should have sent a written acknowledgment. more stringent rules if  over $500 and even different rules if $5000 or more. 

12/31 is the worst date to do tax mitigation when a third-party is involved. Often something goes wrong. Usually, this happens when taxpayers try to take RMDs (sometimes even a few days earlier). The funds aren't transferred out until the next year, which means the taxpayer failed to take the RMD for that year. However, at least for RMDs, corrective action can be taken.

[Opus 17]

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@Mike9241 wrote:

2026 because the items weren't sent until that year. If $250-$500, the Charity should have sent a written acknowledgment. more stringent rules if  over $500 and even different rules if $5000 or more. 

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I have to respectfully disagree on the basis of the constructive receipt rule (and the inverse).

Publication 526 says 
Time of making contribution.
Usually, you make a contribution at the time of its unconditional delivery.
Checks.
A check you mail to a charity is considered delivered on the date you mail it.
Conditional gift.
If your contribution depends on a future act or event to become effective, you can’t take a deduction unless there is only a negligible chance the act or event won’t take place.
If your contribution could be undone by a later act or event, you can’t take a deduction unless there is only a negligible chance the act or event will take place.
 
There is a tension between "unconditional delivery" and some of the other terms, for example a check is deducted when it is mailed (assuming there are funds in the account), not when the check is delivered to the charity.  If you put clothes in a Goodwill dropbox on 12/31, that is unconditional delivery, even if a snowstorm prevents the charity from picking up from the drop box until January.
 
Or think about a business where the client mails a check on 12/31.  The client can report it as a past year expense while the business records it as next-year income. 
 
In the case of buying items for a charity from (let's say) their Amazon wish list, I would argue that the donation is made when the order is placed, assuming the contribution cannot "be undone by a later act or event", but if the contribution could be undone by a later act (i.e. canceling the order) then the contribution is not made until there "is only a negligible chance" of undoing the order.
 
I agree the taxpayer also needs (in addition to their proof of purchase) an acknowledgment from the charity of the gifts received, and in this case the acknowledgment will be dated 2026.  But that's the same kind of paperwork mis-match that occurs when a client pays a business on 12/31/2025 and issues a 2025 1099-NEC and the business does not report it as income until 2026.  This situation must happen all the time and I'm sure the IRS can deal with it (if audited, the taxpayer can show their purchase records to support why the acknowledgment is different.)