Hi Nick Anderson,
Which version of Windows Surface Pro are you using?
If I remember right Surface Pro 7 and up can get Windows 11 which is supported.
When its not updating are there any error codes in Windows Update or event viewer?
Have you tried deleting the contents of the download folder in the Software Distribution folder under Windows, this will force WU to download a new copy of the update.
Are you using 3rd party anti-virus app?