@RBCopland
ArcGIS Pro cannot automatically check for an update when using a checked out license (offline mode). Suggest check: ArcGIS Pro > Project > Licensing > Settings. If Authorized to work offline, return checked out license and run ArcGIS Pro with the appropriate licensing portal. You may need to consult your co-worker or the GIS administrator.
Ayan Palit | Principal Consultant Esri