My wife’s MBP (13", 2014 or so, always running latest OS X) has been happily running Build 154. The update to 157 failed, with the Roon icon in the task bar turning to a generic one, and Roon failing to start (sorry, I didn’t note the precise error message).
An attempt to download from the website and install over the top of the previous installation also failed, with OS X claiming Roon.exe is damaged when I try to run it.
Sophos Home was running, so I turned it all off, and tried again. Same result.
Is this failing install just running as a client ? If so, then I would delete the Roon folder and do a complete fresh install (rather than laying one over the other).
If it still fails then we have to look a bit deeper.
All the time it was failing, I was trying to update Roon in my wife’s user (she is an administrator - it’s her laptop). When I did it in my user (also an administrator), from which I probably originally installed Roon, it worked fine.
This is probably a side-effect of Roon installing in a user directory despite being a multi-user application. (I never understood that but I’ll bet there’s a reason!)
but if you have some file issues then all bets are off that an upgrade is guaranteed to work.