Yep: as my screenshots show, the Tesla app is running (both foreground and background tested) with all of the dependencies set. I have now accepted the fact the phone needs to be present for the popup or any calendar even if it is downloaded: as a design choice, this protects the privacy of the phone holder (presumably if you have the phone you have access to the calendar and contacts, screen lock/Touch ID notwithstanding).
Looks like others are indeed having this issue, yet others are not with similar configs. Could it be VIN related? Mine is #16225, Canadian MS.