Deductions & credits

My spouse has delayed medicare and social security while working. We understand that. The issue is that even if you delay it until the month after you quit, there is still a 6-month look-back for medicare which can cost you penalties with the IRS if you don't deal with the HSA properly. We just keep getting the run around and keep getting referred back to other people. I've called the IRS. They won't talk about anything at all having to do with healthcare or penalties. Period. I followed every phone tree I could, and it always ended telling me they won't talk to us about it and to see their website. I finally pulled a trick and got to a live person in another department, and they were annoyed and said they can't talk to me about it and to call medicare. When I called medicare, they said talk to the IRS. When I called the HSA Administrator, they didn't even know they had a pdf on their website about the topic. I tried to get clarification on the pdf, and they referred me to the employers HR or a tax advisor. I emailed HR, and they referred me back to the HSA administrator. The only person I haven't called is a tax advisor - because we use TurboTax! It is all insane, which is actually what the pdf said. See this quote:

"Medicare and HSA eligibility

Many individuals are confused at the intersection of health
savings accounts (HSAs) and Medicare. Two different federal
agencies have primary responsibility for these programs — the
Department of Health and Human Services, for Medicare,
and the Department of the Treasury, for HSAs. Each agency
issues rules related to its products without consideration of the
interaction with the other product, leaving Americans confused.
This paper is designed to help you navigate this confusion so
that you remain in compliance with HSA rules."

So, I read the "paper" and am still confused. The employer responded by saying they think we can just put our entire year's worth of contribution into the HSA in the first couple months, and keep it in there if we don't put any in within the 6 months prior to getting on Medicare. But, they were not sure, and I can't trust them to know. They also seem to think we can keep the employer contribution even if it is put in there in the previous 6 months, but, again, they are just guessing. It is very frustrating.