Timing of expenses in self-funded insurance welfare plan

[bzorc]

I have a client who maintains a self-funded insurance plan. The plan year is a June 1 to May 31. The corporations taxable year is the calendar year. The partner that I work for has, for other clients, had the client prepay 30-35% of the next year's premium during the current year, and treat that payment as an expense on the current year corporate tax return. However, he is unsure as to whether or not this practice would work if the corporate year and plan year do not coincide.

I have no idea if this question makes any sense, but if it does to someone, your comments would be appreicated. Thanks.