Specifically what are you managing per context which you couldn’t do via application.cfc?
I will knock up some GitHub actions integration tests for multi site next week over on Lucee testlab, building off the work I did on for the installer
We can then collaborate on trying to reproduce the problem, if my initial attempts fail to reproduce the issue
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Ah that would be amazing, thank you so much! We can easily spin up test VMs to run clean installs 
In regards to question on per context, we have a range of levels using our platform, so many prefer to manage their site using a UI in terms of adding datasources, viewing logs, configuring performance related settings.
Also, having a context in the current form also allows a level of security as end users code is isolated to their own domain/context.
@Zackster is one of the lead developers. He of all people understands the internals of the code. I just manage to get things working right or not 