Thanks for the report. As the first step, please ensure you have the latest Roon version installed. If the issue is still happening on the latest Roon version, can you please confirm -
If you uncheck and then re-check start at startup, does that trigger any change in behavior?
Does this only occur after a Roon update or regardless of the time?
Does this issue only affect Roon UI / Roon Server / or both? (Is the Roon icon visible in the taskbar)?
Have you made any macOS updates since it was working vs when it stopped working?
Are you still experiencing this on the latest version of Roon? Build 1582 contained a fix for the GUI crash on Tahoe that might have an effect on the symptom you reported here.
Please let us know if you still require assistance. Thanks!