"Error: Failed to start ROV" when ROV tries to connect for the first time for specific projects. When pressing the CONNECT button again, ROV will succeed in connecting.

As mentioned, it doesn't happen with all projects. One such project that it does occur with is:

https://dev.ti.com/tirex/explore/node?node=A__ALl.2FW.Sds.SyEYZCa9Dw__com.ti.SIMPLELINK_CC13XX_CC26XX_SDK__BSEc4rl__LATEST

Customer was on CC1312, I used CC1352

This issue appears to be specific to macOS. I could not reproduce on Windows.