Qualifying for a charitable deduction is, in some respects, a matter of form over substance. The IRS could disallow a deduction, even if it’s otherwise legitimate, if you fail to follow the substantiation requirements to the letter. Here’s a quick summary of the rules.

Cash gifts

Generally, you can substantiate gifts of less than $250 with a canceled check, written receipt or other reliable record (such as credit card statements) that indicates the name of the charity and the amount and date of your gift. Separate gifts of less than $250 generally are treated separately for these purposes, unless they’re made on the same day. For example, if you write a $200 check to your favorite charity once a week, each check is treated as a separate gift under the $250 threshold. But if you write two checks on the same day, they will be treated as a $400 gift subject to the substantiation requirements discussed below.

If you donate more than $75 in exchange for goods or services other than intangible religious benefits (such as admission to religious ceremonies), the charity must provide you with a statement that 1) advises you that your deduction is limited to the amount by which your gift exceeds the value of those goods and services, and 2) provides a good-faith estimate of that value.

Gifts of $250 or more require a “contemporaneous” written acknowledgment from the charity that includes the amount and date of your gift, the estimated value of any goods or services you received, and any intangible religious benefits provided. An e-mail will suffice.

To satisfy the contemporaneous requirement, you must have the acknowledgment in your possession before you file your income tax return or, if earlier, before the extended due date of your return.

Noncash gifts

If you make noncash gifts totaling more than $500 for the year, you must file Form 8283, “Noncash Charitable Contributions,” with your federal income tax return. And for gifts of property valued at more than $5,000 ($10,000 for closely held stock) you’ll need to obtain a “qualified appraisal” by a “qualified appraiser” and have the appraiser sign Sec. B, Part III, “Declaration of Appraiser.” If property is valued at more than $500,000, you’re required to attach a copy of the appraisal report to your return. No appraisal is required for publicly traded securities, regardless of value.

A qualified appraiser is a professional who meets certain education, experience and accreditation requirements. A qualified appraisal must 1) be prepared, signed and dated by a qualified appraiser other than the taxpayer or donee, 2) be conducted within 60 days of the gift, 3) provide certain information about the property, the appraiser and the valuation methods used, and 4) not involve fees based on a percentage of the appraised value or deduction amount.

There are special rules for gifts of art, clothing, household items and used cars.

The cost of noncompliance

A recent U.S. Tax Court case demonstrates the importance of compliance with IRS substantiation rules, particularly the qualified appraisal requirement. In Ben Alli v. Commissioner (T.C. Memo. 2014-15), the court disallowed a nearly $500,000 charitable deduction because the two appraisals obtained by the taxpayer failed to meet the requirements for a qualified appraisal.

The taxpayer donated an apartment building to a charity and claimed a $499,000 charitable deduction based on two appraisals. The Tax Court found both appraisals to be deficient. The first appraisal was conducted 10 years before the contribution, not within 60 days, as required. In addition, it failed to apply any of the commonly recognized valuation methods.

The second appraisal was conducted five months before the contribution, so it too was untimely. But, more significant, it was based on a “hypothetical, fully renovated version of the contributed property,” when in fact the building was in poor condition.

Don’t leave it to chance

If you’ve made substantial charitable donations, their deductibility depends on compliance with IRS substantiation rules. When in doubt, consult your tax advisor to be sure you’ve dotted all the i’s and crossed all the t’s.