Integrate Jira Server with IIS Using Application Request Routing

Summary

This article provides a comprehensive guide on integrating Jira Server with Microsoft's IIS using Application Request Routing (ARR). It outlines the necessary configurations and steps to ensure seamless integration, enhancing the routing capabilities and management of Jira applications. The guide is essential for administrators looking to optimize their Jira Server setup with IIS, leveraging ARR for improved performance and reliability.

Solution

1. Install Application Request Routing and URL Rewriting on your IIS server.

2. Enable Proxying on ARR:

   1. From the IIS7 Console, click on Server_Name and open Application Request Routing:

      

   2. From the Actions panel on the right hand side, select "Server Proxy Settings"

   3. Check "Enable Proxy" and set HTTP Version to "HTTP/1.1":

      
      Make sure to disable "Reverse Rewrite Host in Response Headers" - this can cause problems with URLs being re-written incorrectly:

      1. Click on your Server in the sidebar

      2. Click "Application Request Routing Cache"

      3. Click "Server Proxy Settings"

      4. Untick "Reverse rewrite host in response headers"

3. Add a new site on IIS (e.g, jira.example.com).

4. Add a new URL Rewrite Rule for jira.example.com:

   1. From the IIS7 Console, click on jira.example.com and open URL Rewrite:

      

   2. From the Actions panel on the right hand side, select "Add Rules" and choose "Blank Rule";

   3. Set Match URL to:

      1. Requested URL: Matches the Pattern

      2. Using: Regular Expressions

      3. Pattern: (.*)

      4. Ignore Case: Checked

   4. Set Action to:

      1. Action Type: Rewrite

      2. Rewrite URL: http://<JIRA_url:Port>/{R:1}

      3. Append query string: Checked

   5. Mark Stop processing of subsequent rules;

      

5. Click on Request Filtering

   

6. Then click on Edit Feature Settings

   

7. Check Allow double escaping and hit OK

   

8. Now add this comment to your <jira-install>/conf/server.xml:

   <Connector port="8080" connectionTimeout="20000" redirectPort="8443" maxThreads="200" minSpareThreads="10" enableLookups="false" acceptCount="10" debug="0" URIEncoding="UTF-8" />

9. Add the parameters proxyName and proxyPort to your <JIRA-install-directory>/conf/server.xml file in Jira, as in this example:

   <Connector acceptCount="100" connectionTimeout="20000" disableUploadTimeout="true" enableLookups="false" maxHttpHeaderSize="8192" maxSpareThreads="75" maxThreads="150" minSpareThreads="25" port="8080" protocol="HTTP/1.1" redirectPort="8443" useBodyEncodingForURI="true" proxyName="jira.example.com" proxyPort="80"/>

10. Restart your Jira application.

Optional

In some cases more than one site will be hosted in the same IIS installation. In case you want to have a subdomain structure (i.e. jira.example.com, confluence.example.com), you may create different sites as follow:

1. Create an A Record in the DNS for your subdomain and point to the same IP:

   

2. Create new sites (step 3 of the instructions above) for each one of your subdomains:

   1. Sites > Add Website

   2. Site Name: subdomain.example.com

   3. Physical Path: select the subdomain directory

   4. Binding: same IP as example.com

   5. Host name: subdomain.example.com

      

   Known Issues

   • Elements in Jira server fail to render with 400 bad request error

   • User session changed or hijacked in Jira server integrated with IIS

   • HTTP Error 500.51 when attempting to access Jira through IIS