Currently I am living in an Assisted Living Program in New York State. I am on Medicaid. I just turned 59. I will have to start taking money from my 401k soon. My question is will I go into Medicaid spend down, or will I ''lose Medicaid '' until I get down to the 14,000.00 dollars (estimated) that Medicaid allows you to keep?

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If I understand what I’ve read on this forum you will need to spend any money you receive in one month so it doesn’t raise your monthly balance reported to an amount over that allowed.
It has to be spent on your care. It needs to arrive to your bank account at the right time of the month in order to have time to dispense it that same month. As an example perhaps you need extensive dental work done. You would need to be make sure the payment clears your bank account on time.
You could pay for your funeral or cremation. Things that are for you and allowed and can clear in one month.
I think I would see a certified elder attorney to make sure you are handling it correctly. The attorney fee would be acceptable. There are possibly other ways to manage your 401 to keep you from going out of compliance.
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