For those coming along later, here is the exact server.xml that works:

<?xml version="1.0" encoding="utf-8"?> <!-- Licensed to the Apache Software Foundation (ASF) under one or more contributor license agreements. See the NOTICE file distributed with this work for additional information regarding copyright ownership. The ASF licenses this file to You under the Apache License, Version 2.0 (the "License"); you may not use this file except in compliance with the License. You may obtain a copy of the License at http://www.apache.org/licenses/LICENSE-2.0 Unless required by applicable law or agreed to in writing, software distributed under the License is distributed on an "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied. See the License for the specific language governing permissions and limitations under the License. --> <Server port="8005" shutdown="SHUTDOWN"> <Listener className="org.apache.catalina.startup.VersionLoggerListener"/> <Listener className="org.apache.catalina.core.AprLifecycleListener" SSLEngine="on"/> <Listener className="org.apache.catalina.core.JreMemoryLeakPreventionListener"/> <Listener className="org.apache.catalina.mbeans.GlobalResourcesLifecycleListener"/> <Listener className="org.apache.catalina.core.ThreadLocalLeakPreventionListener"/> <Service name="Catalina"> <!-- ============================================================================================================== DEFAULT - Direct connector with no proxy for unproxied access to Jira. If using a http/https proxy, comment out this connector. ============================================================================================================== --> <!-- <Connector port="8080" maxThreads="150" minSpareThreads="25" connectionTimeout="20000" enableLookups="false" maxHttpHeaderSize="8192" protocol="HTTP/1.1" useBodyEncodingForURI="true" redirectPort="8443" acceptCount="100" disableUploadTimeout="true" bindOnInit="false"/> --> <!-- ============================================================================================================== HTTP - Proxying Jira via Apache or Nginx over HTTP If you're proxying traffic to Jira over HTTP, uncomment the below connector and comment out the others. Ensure the proxyName and proxyPort are updated with the appropriate information if necessary as per the docs. See the following for more information: Apache - https://confluence.atlassian.com/x/4xQLM nginx - https://confluence.atlassian.com/x/DAFmGQ ============================================================================================================== --> <!-- <Connector port="8080" maxThreads="150" minSpareThreads="25" connectionTimeout="20000" enableLookups="false" maxHttpHeaderSize="8192" protocol="HTTP/1.1" useBodyEncodingForURI="true" redirectPort="8443" acceptCount="100" disableUploadTimeout="true" bindOnInit="false" scheme="http" proxyName="jira.a-closer-look.com" proxyPort="80"/> --> <!-- ============================================================================================================== HTTPS - Proxying Jira via Apache or Nginx over HTTPS If you're proxying traffic to Jira over HTTPS, uncomment the below connector and comment out the others. Ensure the proxyName and proxyPort are updated with the appropriate information if necessary as per the docs. See the following for more information: Apache - https://confluence.atlassian.com/x/PTT3MQ nginx - https://confluence.atlassian.com/x/DAFmGQ ============================================================================================================== --> <Connector port="8080" maxThreads="150" minSpareThreads="25" connectionTimeout="20000" enableLookups="false" maxHttpHeaderSize="8192" protocol="HTTP/1.1" useBodyEncodingForURI="true" acceptCount="100" disableUploadTimeout="true" bindOnInit="false" secure="true" scheme="https" proxyName="jira.a-closer-look.com" proxyPort="443"/> <!-- ============================================================================================================== AJP - Proxying Jira via Apache over HTTP or HTTPS If you're proxying traffic to Jira using the AJP protocol, uncomment the following connector line See the following for more information: Apache - https://confluence.atlassian.com/x/QiJ9MQ ============================================================================================================== --> <!-- <Connector port="8009" URIEncoding="UTF-8" enableLookups="false" protocol="AJP/1.3" /> --> <Engine name="Catalina" defaultHost="localhost"> <Host name="localhost" appBase="webapps" unpackWARs="true" autoDeploy="true"> <Context path="" docBase="${catalina.home}/atlassian-jira" reloadable="false" useHttpOnly="true"> <Resource name="UserTransaction" auth="Container" type="javax.transaction.UserTransaction" factory="org.objectweb.jotm.UserTransactionFactory" jotm.timeout="60"/> <Manager pathname=""/> <JarScanner scanManifest="false"/> </Context> </Host> <Valve className="org.apache.catalina.valves.AccessLogValve" pattern="%a %{jira.request.id}r %{jira.request.username}r %t &quot;%m %U%q %H&quot; %s %b %D &quot;%{Referer}i&quot; &quot;%{User-Agent}i&quot; &quot;%{jira.request.assession.id}r&quot;"/> </Engine> </Service> </Server>