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Problem

Plugin Start up Fail / Plugin Timeout 

Solution

For Linux : It is possible to increase the plugin timeout period by adding the "-Datlassian.plugins.enable.wait=300" argument to the JIRA arguments
  1. From <jira-install>/bin (or <Tomcat-home>/bin for JIRA WAR installations), open setenv.sh.
  2. Find the section JVM_SUPPORT_RECOMMENDED_ARGS=-Datlassian.plugins.enable.wait=300

For Windows :

  1. From <jira-install>/bin (or <Tomcat-home>/bin for JIRA WAR installations), open setenv.bat.
  2. Find the section set JVM_SUPPORT_RECOMMENDED_ARGS=-Datlassian.plugins.enable.wait=300

Note this allow the plugin to start within 5 min. of time stamp. You can keep it low also as per your requirement.