I'm so confused with the "Upgrade" example. Why does it lose the title case and why does it end up phrased as "upgrade to" instead of "Upgrade"?
So it isn’t randomly translating “upgrade" as "upgrade to." The context tells you that "upgrade” means "move to a different plan," rather than "update the software."
You're right about the random capitalization though - it wasn't intentional and we'll edit that bit to avoid confusion.