My view is that if the individual's status is not clearly within the 4 corners of the policy (fully insured group or stop loss, which will wrap the SPD), you have a potential for claims to be denied if they are large, and for employer to be stuck in the middle, having promised something to the "employee" that an insurer won't pay for. Usually I tell client that they need to disclose in a letter to the insurer how they are interpreting "employee" to include this person.