Starting with platform server Release Apr.2019 CP1, 11.0.424 the installer give us a generic error when trying to update the platform server on a Windows Server 2019 machine, but don't says nothing about not supported Windows Server version.
Later versions support this without any error, but the platform version that Lifetime comes with is still locked on the version that brings the generic error and doesn't support Windows Server 2019 version.
We are waiting since Jul/19 for features we need of last versions of Lifetime.
Specially the last about permissions granularity that were causing us many problems in restricting devs to publish modules that use some system refs.
Please update as soon as possible the platform version embed with Lifetime installer.
People please upvote this to help Outsystems be more aware of it.
I already have opened a ticket with support.