Alimony treatment depends on one date: December 31, 2018. Payments under an agreement entered on or before that day keep the classic paired treatment — deductible by the payer, includable by the recipient — unless a post-2018 change expressly provides the receipts are excluded. Payments under an agreement entered after that day get neither half: no deduction, no inclusion. The adviser's first question is therefore always the execution date of the instrument.
The second question is what the payments are. Even under a grandfathered agreement, five categories never count: child support, noncash property settlements, the spouse's share of community income, upkeep of the payer's own property, and use of the payer's property. A payer covering the mortgage on his own home where his spouse lives rent-free deducts nothing — the mortgage and the home are his. Property division itself travels a separate track: transfers incident to divorce (within 1 year after the marriage ends, or related to its end) carry nonrecognition — no gain or loss on the first transfer — rather than alimony treatment.
A grandfathered agreement has one more rule. When alimony payments decrease or end during the first 3 calendar years, the recapture rule can pull previously deducted amounts back: in the third year the payer includes part of the alimony previously deducted in income, and the recipient deducts part of the alimony previously included. Recapture applies when third-year alimony drops by more than $15,000 from the second year, or second- plus third-year alimony drops significantly from the first year. Both spouses figure the amount on Worksheet 1, which applies $15,000 floors and excludes temporary support orders, fixed income-share payments, and decreases caused by death or remarriage.
Worked example
Rex pays $24,000 a year under a 2016 agreement, never modified: $18,000 labeled alimony plus $6,000 labeled child support. The $18,000 is deductible by Rex and includable by his ex-wife under the pre-2019 rule; the $6,000 is excluded from alimony by category. Had the same agreement been executed in 2021, the entire $24,000 would have no alimony treatment — Rex deducts nothing and his ex-wife includes nothing — while the $6,000 child support stays excluded from alimony either way.