Accelerating alimony to get deductions earlier

I pay $36k/year in alimony that is deductible to me. I have 29 more payments of $3k/month to go for a total of $87k. I am going to have some large stock option gains this year. Am I allowed to prepay some of my alimony payments from future years and take the deduction this year to offset some of those gains?

posted

In general, no. Alimony must be required by a court order, divorce order, and so on, and extra payments would be viewed as voluntary, and therefore not considered deductible alimony. I suppose that if you and your ex agreed to accelerate the payments, and got the court to sign off on the plan, then it would be an allowable deduction.