Set properties from .properties file in .jar on JVM startup?

No, it's not possible to have the system properties loaded from a file automatically. What you can do is have some sort of launcher that reads a file and automatically "translates" it to -D command line options.

If you are using Maven to package your application, consider using the appassembler-maven-plugin's generate-daemons goal. This will generate JSW based daemon wrappers for Windows and linux. So the bat/sh file used to launch the application will have those properties defined, while still allowing you to specify additional properties via the command line.

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