I’m reading through Carmen Ebner’s PhD thesis one more time (defense coming up soon!), and it strikes me in my own writings, too, every time – the red squiggles under prescriptivism, as in the header to this post. It makes me terribly insecure: is the second r in place? What is wrong with the word, why don’t they like it, over at Microsoft?
Bridging the Unbridgeable 
Microsoft thinks about what they put in their dictionary? There is a whole pile of words in Merriam-Webster’s that Microsoft claims is wrong and vice versa. Why is there no option to load a legitimate dictionary? Probaby the same reason that all of Word’s other longstanding problems aren’t fixed.
I added it to my Word dictionary long ago for just this reason.