Steps to Reproduce:

1. Integrate JIRA with Apache following the guide:
   • Integrating JIRA with Apache
2. An example of server.xml

   <Connector acceptCount="100" connectionTimeout="20000" disableUploadTimeout="true" enableLookups="false" maxHttpHeaderSize="8192" maxThreads="150" minSpareThreads="25" port="8766" protocol="HTTP/1.1" proxyName="testing.com" proxyPort="80" redirectPort="8443" useBodyEncodingForURI="true"/>
   

           <Engine defaultHost="localhost" name="Catalina">
               <Host appBase="webapps" autoDeploy="true" name="localhost" unpackWARs="true">
   
                   <Context docBase="${catalina.home}/atlassian-jira" path="/jira" reloadable="false" useHttpOnly="true">
   

3. With the configuration on Apache Proxy side:

   <VirtualHost *:80>
       ServerName testing.com
       
       <Proxy *>
               Order deny,allow
               Allow from all
       </Proxy>
   
       ProxyRequests           Off
       ProxyPreserveHost       On
       ProxyPass               /jira       http://localhost:8766/jira
       ProxyPassReverse        /jira       http://localhost:8766/jira
   </VirtualHost>
   

4. Start JIRA and restart Apache.
5. Access JIRA through http://localhost:8766/jira

Expected Result:

As mentioned in the documentation:

If the context path is other than empty or root , e.g. /jira , visiting JIRA via the proxy connector (e.g. http://jiraserver:8080/jira) should redirect you to the configured proxy (e.g. https://jira.atlassian.com/jira).

Accessing through the context path will redirect it to the FQDN.

Actual Result:

It will show as mentioned in the documentation where:

If the context path is empty or root , visiting JIRA via the proxy connector (e.g. http://jiraserver:8080/) should take you to JIRA with a warning: