Please help. Ups will not

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He who laughs last didn't get it.
My son has worked for UPS pre loading for 4 years. He recently took a drivers position and passed his 30 day test period. He is an official Driver I guess, but still often pre loads when needed. My question is should he still have health insurance? Right now he has none and has been trying to get answers at work but everyone there just blows him off and are useless!!! They give him a number to call and every time he calls it’s not the correct department. How the hell can he get any answers if his boss is clueless? Please help as he has medications he needs and he can get an answer from anyone. I would assume someone there should have talked to him about his health insurance when he changed positions. Or does he just loose his insurance for a few months when he becomes a driver?
Your son will never be a RPCD