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I have no experience with over employment. But I do have 15+ health insurance exp. Yes you can be the subscriber on two different health insurance policies. Also, losing coverage is a qualifying life event and would allow you to enroll outside the new hire window with your 2nd job. You just need a letter from the previous employer stating what kind of coverage you had (ex. medical) and when it ended. How you came about that coverage (ex. through a family member, a second job, govt program) is irrelevant.