Pretty new to Jenkins and I have simple yet annoying problem. When I run job (Build) on Jenkins I am triggering ruby command to execute my test script.
Problem is Je
The Operating-System is buffering output-data by nature, to save CPU, and so does Jenkins.
Looks like you are using a shell-command to run your Ruby script - I suggest running your Ruby script directly via the dedicated plugin:
Jenkins Ruby Plugin
(may need to install it)