Does the human-resources person have authority to decide such an expenditure without the approval of some other executive?
If the employment-law, business, and other risks beyond employee-benefits law and tax treatment don't deter the decision-maker, is it feasible to amend the health plan's documents to specify exactly who is eligible?
When the employer asks for its lawyers' advice, it might ask whether treating as eligible or covered persons who are not so entitled under the plan documents' provisions is a breach of a fiduciary's duties of obedience, loyalty, impartiality, or prudence?