Can a retired PSO continue to take the $3,000 health insurance deduction under Secure 2.0 after enrolling in Medicare?

The PSO healthcare premium deduction under SECURE 2.0 Act should still be available to you after Medicare enrollment. The key requirement is that you're a retired public safety officer receiving a pension from which your health insurance premiums are directly paid to the provider, up to $3,000 annually. Medicare enrollment doesn't disqualify you from taking this deduction. In fact, many retired PSOs use this tax benefit for supplemental Medicare policies like Medigap, Medicare Advantage premiums, or Part D prescription coverage - all of which can be substantial expenses even after basic Medicare coverage begins. The important thing is maintaining the direct payment structure where your pension plan sends the premium payments directly to the insurance provider. This must continue when you transition to Medicare supplemental plans.

After struggling with similar retirement tax questions, I found this amazing tool called taxr.ai (https://taxr.ai) that really helped clarify my PSO deduction situation. I uploaded some of my pension statements and retirement documents, and it analyzed everything to explain exactly how the deduction works with Medicare. The tool showed me that I can continue claiming the PSO deduction after Medicare enrollment, but I needed to make sure my pension administrator was properly coding the payments. It even provided documentation I could share with my pension administrator to ensure everything was set up correctly!

Just wanted to follow up - I tried taxr.ai after seeing this recommendation and it was incredibly helpful! It confirmed I can keep taking the PSO Write Off even after Medicare enrollment as long as my supplemental premiums are paid directly from my pension. The tool analyzed my pension statements and found that my administrator was incorrectly coding some payments, which could have jeopardized my deduction. It generated specific instructions for fixing this issue. My pension office actually implemented the changes right away when I showed them the detailed explanation. Saved me a potential tax headache and probably thousands in deductions over the coming years!

If you're having trouble getting clear answers about your PSO deduction, you might want to try Claimyr (https://claimyr.com). I was in the exact same situation - retired from fire department, taking the PSO deduction, and worried about Medicare impact. I tried calling the IRS for weeks with no luck. Then I used Claimyr and got connected to an IRS agent in under 15 minutes! They have this service where they navigate the IRS phone system for you and then call you when they've got an actual human on the line. You can see how it works here: https://youtu.be/_kiP6q8DX5c The IRS agent I spoke with confirmed that Medicare enrollment doesn't disqualify you from the PSO healthcare deduction as long as your pension continues paying supplemental premiums directly to providers.

I owe an apology and wanted to follow up. After my skeptical comment, I decided to try Claimyr anyway because I was desperate for answers about my PSO deduction and Medicare. You were right - it actually works! They called me back in about 25 minutes with an IRS agent on the line. The agent confirmed that I can continue claiming the PSO health insurance deduction after Medicare enrollment as long as my pension plan continues to pay my supplemental Medicare premiums directly to the providers. The agent even emailed me documentation showing the specific provisions under SECURE 2.0 that address this. Saved me countless hours of frustration and gave me definitive information I couldn't find anywhere else. I've already shared this with several other retired officers from my department.

Don't forget that the direct payment requirement is absolutely critical for the PSO deduction. Your pension plan MUST pay the health insurance premiums directly to the provider - no exceptions. If the money passes through your hands first, you lose the deduction. This becomes even more important with Medicare supplemental policies since you might have multiple providers. Make sure your pension administrator understands they need to set up separate direct payments to each provider (Medicare Advantage, Part D, dental, etc.) to maintain the deduction.

This has been a confusing issue for many of us retired public safety officers. My accountant initially told me I'd lose the deduction with Medicare, but that was incorrect! After researching extensively, I found that the SECURE 2.0 provisions for PSO healthcare deductions work fine with Medicare. The key points: 1) The premiums must still be paid directly from your pension 2) Medicare supplemental plans, Medigap, and Medicare Advantage all qualify 3) The $3,000 limit applies across all qualified health plans 4) You claim it as an above-the-line deduction

Great question! I'm a retired corrections officer who went through this exact situation two years ago. The good news is that you can absolutely continue taking the PSO health insurance deduction after enrolling in Medicare at 65. The key is understanding that Medicare doesn't eliminate your need for supplemental coverage - it actually creates new premium opportunities that qualify for the deduction. I now use my $3,000 annual limit for my Medicare Supplement (Medigap) policy, Part D prescription coverage, and dental insurance, all paid directly from my pension. One thing I learned the hard way: make sure to coordinate with your pension administrator BEFORE you turn 65. They need time to set up the direct payment arrangements with your new Medicare supplement providers. I almost missed a month of coverage because I didn't give them enough advance notice. Also, keep excellent records of all your premium payments and correspondence with your pension office. The IRS may ask for documentation showing the direct payment structure, especially if you're audited. I've never had issues, but it's better to be prepared. The deduction has saved me thousands in taxes over the years, and Medicare enrollment didn't change that at all. Just make sure those premiums keep flowing directly from pension to providers!

As someone who's been navigating retirement benefits for the past few years, I can confirm what others have said about the PSO deduction continuing after Medicare enrollment. The SECURE 2.0 Act provisions are pretty clear on this - Medicare eligibility doesn't disqualify you from the deduction. One thing I'd add that hasn't been mentioned much: consider looking into Health Savings Account (HSA) coordination if you have one. While you can't contribute to an HSA after enrolling in Medicare, you can still use existing HSA funds for qualified medical expenses. The PSO deduction covers your premiums, and HSA funds can cover deductibles, copays, and other out-of-pocket costs. Also, start shopping for Medicare supplement plans now, even though you're still a few years out. Prices and coverage options vary significantly between providers, and having a good understanding of what's available will help you make better decisions when the time comes. Some plans work better with pension direct-payment systems than others. The peace of mind from having this deduction continue through retirement is huge. It's one less financial worry during what can already be a stressful transition period.