When does Microsoft’s health insurance start? Is it the first day of employee start date or 1st of the month?

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Don’t know why Microsoft would do it differently. Typically you sign up for a plan within first couple of weeks after joining but coverage is backdated to your first day of joining the company. That is, if you need to avail any medical service before you get your medical insurance number, you can do that and it’ll run through your insurance later. However, for the ease of processing etc I would avoid elective procedures / visits until you have an active insurance (an insurance ID) - just makes dealing with billing easier on the provider side.

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