Turn Passcode Off grayed out Context

I have recently acquired a series 1 Apple Watch. When I first started setting it up, I added a passcode out of habit. Now I want to temporarily disable the passcode as I'm continuing to do a lot of setup off of my wrist and it's getting tedious having to enter the code over and over.

The Problem

The option to "Turn Passcode Off" is grayed out on both my iPhone (in the Watch app) and on the Apple Watch itself. How do I enable either button in order to disable the passcode?
Exchange mail and configuration profiles (generally installed by a workplace or school) can also enforce a passcode. To disable the passcode in this case you'll have to either remove the profile or the account.