Hello,
We are also experiencing the issue. Important to note, enterprise environment, uses SCCM/MECM for updates.
We enable updates directly from Microsoft adn apply the latest drivers and firmware and most of these issues have gone away - although, some of our machine which are using docks needed additional firmware (see this link - https://support.microsoft.com/en-us/help/4023478/surface-update-your-surface-dock)
Having said this, we have seen issues with upgrades - which show successful, however, are problematic if the drivers and firmware are not updated to a compatible version of the target OS version (in our current case 20H2).
Hope this helps.