Why can't I use "cut path" on this

[KeystoneChuck]

I've been trying to cut out simple sayings and I can not use the cut path feature to finish my saying. I outline the word then use the cut path to get rid of the unwanted material; but when it comes to cutting inside a letter the cut path command only works on some of the letters. I made a simple "M" letter to show you what I mean. I outlined the entire project. Used the cut path feature for the outside but when I try to use cut path for the inside of the "M" it is not avaliable to use. Any ideas?