Since "BandLab Cakewalk activation upd" likely refers to the (moving from a free, activation-key model to a paid subscription/ownership model), this review covers that specific shift and the current state of the software.
Major Windows updates (like 22H2 to 23H2) often reset permission settings. Simply re-run as Administrator, and the UPD will fix itself.
BandLab Cakewalk Activation Update: Navigating the Sunsetting of CbB and Transitioning to Sonar
No. Cakewalk caches your activation for a period (usually 7–14 days). If you’re offline when it tries to do an “activation upd,” it will continue working until the grace period ends. After that, it will ask you to go online to refresh.