I ran into a lot of issues when trying to figure this out. Here is my setup,
Dev Env : Windows 10, Java : 1.8.0_25, Spring Boot : 2.0.3.RELEASE, Spring : 5.0.7.RELEASE
What I found is spring is sticking with the concept "Sensible defaults for configuration". What this translates in to is, you have to have all your property files as part of your war file. Once in there, you can then override them using the "--spring.config.additional-location" command line property to point to external property files. But this will NOT WORK if the property files are not part of the original war file.
Demo code: https://github.com/gselvara/spring-boot-property-demo/tree/master