First, thank you all for considering my question and offering your replies. I work in MA at a very small <10 employees firm. They have been offering $X per month in pretax gross-up of our income when we show them an insurance bill. So, in effect, we have company-paid coverage, but all staff must get their own policies. One of our staff has asked that the our company pay him the difference between one person covered versus two covered in his spouse's company insurance plan. (Make sense? If her coverage were $500, and both are $800 -- he is asking for $300 per month.) From my days of owning a company and offering benefits (well before the days of ObamaCare and newer laws) I would have thought this was not legal to in essence, pay your employee not to take coverage, and pay them to get coverage elsewhere. I would not care much about this, except that one of the reasons that our company will not just go out and get a group plan that we could either take or leave is that this employee wants to get the payout, and that would not happen if we did offer a group plan. Any thoughts on this? Is it legal? My boss needs some guidance and frankly is not too bright about this sort of thing. I would love to be able to offer counsel -- and if possible links to further reading. Again, thank you!