Can I still deduct Alimony/Spousal Support on taxes if divorced pre-2019 but had child support modified after 2019?

The good news is that you should still be able to deduct your alimony payments. The 2019 tax law change (Tax Cuts and Jobs Act) only affects divorce or separation agreements executed after December 31, 2018. Modifications to child support arrangements after that date don't impact the tax treatment of your alimony payments that were established in a pre-2019 divorce. What matters is when your divorce agreement that established the alimony was finalized. Since yours was finalized in 2018, the alimony remains deductible for you (and taxable income for your ex) even with later modifications to child support. The key is that the modification must be specifically for child support, not for the alimony/spousal support portion. If you modified the alimony terms after 2018, that could potentially change the tax treatment.

I went through something similar last year with my complicated divorce situation and found this amazing tool called taxr.ai (https://taxr.ai) that really helped me figure out my alimony deduction situation. I uploaded my divorce decree and modification documents, and it showed me exactly which parts would affect my taxes and which wouldn't. The tool analyzed my documents and explained that as long as the modification doesn't specifically alter the terms of the alimony payments themselves, the tax treatment remains unchanged. It saved me from making a costly mistake on my taxes because I was about to not claim the deduction thinking any modification would invalidate it.

I wanted to follow up about my experience with taxr.ai since I was skeptical at first. After our conversation, I decided to try it with my complex divorce and modification paperwork. Honestly, it was way more helpful than I expected. The system immediately identified that my 2023 modification only changed the custody schedule and child support calculation, leaving the alimony section untouched. It highlighted the specific language in my documents that kept me grandfathered under the pre-2019 rules, which was a huge relief since I can continue deducting about $30,000 annually. My accountant confirmed their analysis was correct. If you're dealing with complicated divorce tax questions, it's definitely worth checking out.

If you're still confused after getting document analysis, you might want to go straight to the source. I spent WEEKS trying to get through to the IRS about a similar alimony question last year. After 11 failed attempts and hours on hold, I found this service called Claimyr (https://claimyr.com) that actually got me through to a live IRS agent in about 15 minutes. You can see how it works here: https://youtu.be/_kiP6q8DX5c I was able to explain my specific divorce modification situation and get a definitive answer directly from the IRS. The agent confirmed that as long as the modification doesn't expressly alter the alimony terms established before 2019, the tax deductibility remains intact. They even documented the call in my account notes so I have something to reference if audited.

I have to publicly eat my words here. After being completely skeptical about Claimyr, I decided to try it for my own alimony tax question since I was getting nowhere with the IRS phone lines. Unbelievably, I got connected to an actual IRS agent in about 20 minutes, after spending literally 3+ hours on hold during my previous attempts. The agent confirmed that my 2022 custody modification didn't impact my grandfathered alimony tax status from my 2017 divorce. She even sent me documentation to keep with my tax records confirming this. For anyone dealing with complex alimony tax questions, especially with the pre/post 2019 rules, getting a direct answer from the IRS saved me from potentially making a very expensive mistake on my taxes.

Here's the specific language from the IRS that addresses your situation: "If you have a divorce or separation agreement executed before 2019, and it is modified after 2018, the modification will not change the tax treatment of the alimony payments unless the modification expressly provides that the alimony isn't deductible by the payer spouse or includible in the income of the receiving spouse." So unless your child support modification explicitly states something about changing the tax treatment of your alimony payments, you're still good to deduct them.

My situation was a little different but might be helpful. My 2017 divorce had both alimony and child support. In 2022, we modified BOTH the child support and alimony amounts because my income changed dramatically. My accountant warned me that because we modified the actual alimony amount after 2018, I lost the grandfather status and can no longer deduct it! So based on my experience, if your modification only touched child support and left alimony completely alone, you should be fine. But if you modified the alimony amount or terms at all, even in the same document as the child support changes, you might have lost the deduction.

This is exactly the kind of complex tax situation where the details really matter. Based on what you've described, since your 2023 modification was specifically for child support (due to your oldest graduating college and youngest changing schools) and your divorce was finalized in 2018, you should still be able to deduct your alimony payments. The key question is whether your modification document touched the alimony terms at all. If it only addressed the child support calculation and left the $2,250 monthly alimony amount and terms completely unchanged, then you maintain your grandfathered status under the pre-2019 rules. However, I'd strongly recommend getting a definitive answer before your quarterly payment deadline. You might want to review your modification paperwork carefully to see if it mentions alimony at all, or consider reaching out to the IRS directly for clarification on your specific situation. The peace of mind of knowing for certain is worth it when you're dealing with $27,000+ annually in deductions.