[MortMan]

Actually - the tax status of the check is immaterial. No matter pre or post tax status, the employer giving money to defray health care costs is against the rule. At least, according to this article.

[fluffy]

Maybe I’m not understanding the problem here... couldn’t the employer just call it a raise and be done with it? Money is money, no need to explicitly say “this is for your health care” it’s just part of the salary.

[EVO X]

Actually - the tax status of the check is immaterial

I am not a tax expert, but I think you're wrong. Business's that give employees an end of year bonus would be penalized.

[IYAS9YAS]

No matter pre or post tax status, the employer giving money to defray health care costs is against the rule. At least, according to this article.

Easy way around it. If you're cutting a separate check, then stop. Bump their pay that amount. Yes, it will be taxable, but it will certainly help with the additional costs.