Thanks for reminding me to follow up here. I emailed with one of your support staff and solved this.
For anyone who happens upon this the root issue is that the role names are case sensitive. This was confusing because the docs listed the Retool groups as lower case, while you'll see them as "start case" in the Retool UI.
The documentation has now been updated and specifies both that the roles are case sensitive and that the internal roles are lower case.