# HSA loophole/strategy

**URL:** <https://discussion.mainstreetbusinesspodcast.com/t/hsa-loophole-strategy/636>\
**Category:** Tax Strategies\
**Created:** [November 11, 2025, 10:12pm UTC](https://discussion.mainstreetbusinesspodcast.com/t/hsa-loophole-strategy/636 "2025-11-11T22:12:54Z")\
**Posts on this page:** 1\
**Page:** 1

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**Author:** ![Benrhilton](https://avatars.discourse-cdn.com/v4/letter/b/e274bd/32.png) [@Benrhilton](https://discussion.mainstreetbusinesspodcast.com/u/Benrhilton)\
**Post date:** [November 11, 2025, 10:12pm UTC](https://discussion.mainstreetbusinesspodcast.com/t/hsa-loophole-strategy/636/1 "2025-11-11T22:12:54Z")

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Mark n Mat. No joke, instead of Metallica, I listen to you guys at the gym. Pumps me up.  
Quick question. I heard Mat talk about this loophole, I mean strategy, in 2024. I just need an HSA qualifying plan for the month of December and can still contribute for the whole year, correct? Just a little clarification if you wouldn’t mind. I usually choose my plan in December and set that up for the following year during open enrollment. I then cancel my HSA qualifying medical plan after January but still contribute the entire amount for that year. Am I doing this backwards? And if so, how can I have a qualifying plan for the month of December if I have to choose it The previous year? Hope that makes sense.