@cissyalice
I associate it with one of the later Windows 10 Pro versions and/or updates (from Dec 2019) which caused the same for me. I'm not sure exactly which one but at the time I suspected KB4598242.
My problem is on a Windows 10 Pro running as a server (presently 20H2.19042.804), which for me means that extremely rarely new software is added and the only thing updating is Windows, Calibre, FreeFileSync and Plex Server - probably in this order of frecuency.
To no avail I've reinstalled Calibre, verified full access to my Calibre installation folder (full rights to Administrators), and tried suspending my antivirus/firewall.
On my desktop I'm running Windows 10 Pro 1909.18363.1379 and have no issue starting the Content Server. On my server I have to run Calibre in admin mode to get the Content Server started.
Cheers!
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