I just picked up a MY17 RR, and tried to update my InControl software which is currently 19B. From searching I understand that is the version that enabled OTA updates, with 22A being the latest? The software won't update however with a "Software up to date" message. Anyone encounter this?

The "Software up to date" message really means a much more ambiguous "no update found".

I've seen this before when the back-end servers were not responding to a request for an update. It may be that the back-end system needs a nudge from a dealer to initiate an over-air update. Worst case is that it will need to be updated manually via the dealer diagnostic system.