It sounds like Blue Cross of Oregon assumed that your employer would be sending payment directly to them for your insurance premium. If your employer compensates you a set amount to get your own health insurance, and you make payment directly to Blue Cross, they should not have an issue with this. Some states allow employers to pay for the Individuals premiums of employees and make payments directly to the insurance company under what is called a list bill. This allows the employer to make the deduction for the epense using pre-ta dollars. This is probably what they are referring to, since Oregon does not require insurance companies to accept list billing from employers who want to compensate employees who purchase their own health insurance. If your employer offers you a monthly bonus, and pays that bonus directly to you, and then you purchase your own health insurance and pay Blue Cross directly, there should be no issues with that. We suggest re-calling Regence Blue Cross Blue Shield and eplaining it to them this way, and see if they have an issue with it. Make sure they understand that you will be responsible for sending them the payment, not your employer. We would guess that the issue is with making your employer responsible for paying the premium directly to them. We could be mistaken on this one, but it sounds more like an issue with how the question was posed to Blue Cross. As far as other options, is your employer willing to shop for a Small Business policy and compare the rates and coverage to his current individual plan? Perhaps by establishing a group health plan, he can obtain better coverage for himself while also insuring you. This would also allow him to use pre-ta dollars to pay for the total insurance premium, thus reducing his payroll ta liabilities.