ody Q: I lost my job in October and my employer agreed to pay COBRA benefits until Jan 1st. I will have health coverage with my new employer on Feb 1st. I’m wondering if I can avoid paying COBRA coverage for Jan, yet still have the option to pay Jan if I have a large medical expense? So my question is about timing. My past employer pays COBRA until Jan 1st. When must I Pay COBRA for the Month of Jan? If I don’t pay anything an we have an accident on Jan 31st can I pay COBRA on Feb 1st and have retro coverage?