Roon 2.65 will not run under Mac OS 10.15.8

See the release notes…

One important note: this release requires macOS 12 or later on Mac, and on Linux requires glibc 2.27 or later plus OpenSSL 1.1.1 or later. If you missed our earlier announcement and want to check whether your system is affected, more details are available in this post.

For Mac users who are not yet able to update to macOS 12 or later, we’re also making a pre-update installer available as a temporary option. This version will not receive future updates or security fixes, and may become incompatible with current Roon Remote or ARC versions over time. You can find the installer here.

Alternatively, you could use OpenCore Legacy Patcher, and run current versions of Roon and MacOS.