Sysout, by definition, outputs to the JVM stdout and stderr I/O channels. Stdout is expected to be a continuous data stream. The only way to route it to rolling files is to first redirect stdout to a file (since the default destination is to the console), then when you want to roll it, stop Tomcat and its JVM, re-assign the stdout channel to a new file, and restart Tomcat. Re-routing of stdout on the fly is not a "write once/run anywhere" capability, so there is no support in pure
Java. Stderr operates identically.
Just for info, the most common Tomcat run scripts redirect the JVM stdout to its logs/catalina.out file. Some people do shut down Tomcat daily and rename this file in order to roll logs.