Thanks for this thorough response. I have added the total amount of premiums paid by the company to the paystub and looked at the W-2 which shows the wages + premiums paid of $15K in box 1 and a corresponding $15K in Box 14. With this being said it shows a credit in the PL for the withholding from the shareholder which is strange since I put the total gross amount of premiums on the paycheck. 

I also do this shareholders personal return so the amount that is in box 14 it will be entered from the W-2 into Health Insurance paid so it is very strange as this is the first year payroll withholding was recorded. Something just does not feel right about this treatment.