Atlassian already have some documentation on how to integrate IIS and JIRA.

Unfortunately it requires installing some ISAPI components, and a whole lot of fiddling around.

I wanted to see if I could get Application Request Routing to do the same job. Turns out, yes, you can – here’s how.

1. Make sure JIRA is installed and working on your server.

Let’s say that it’s at http://example.com:8080/

I want to access JIRA via: http://jira.example.com/ – but IIS7 is already using port 80 on that server.

2. Alter your conf/server.xml file in JIRA.

Find the /Server/Service/Connector element, and add two attributes:

proxyName=”jira.example.com”

proxyPort=”80″

The Connector element should now look something like

 <Connector port="8080" enableLookups="false" proxyName="jira.example.com" proxyPort="80">

3. Restart the JIRA Service.

4. Install, if you havn’t already, Application Request Routing 2.0, along with URL Rewriting 2.0

5. Enable Proxying on ARR:

• From the IIS7 Console, click on {ServerName}.
• Open Application Request Routing.
• From the Actions pane on the right hand side, Select  ‘Server Proxy Settings’
• Check ‘Enable Proxy’
• Set HTTP Version to ‘HTTP/1.1′

6. Add a new site ‘jira.example.com’, with bindings for http://jira.example.com

7. Add a new URL Rewrite Rule for jira.example.com

• From the IIS7 Console, click on jira.example.com
• Open URL Rewrite
• From the Actions pane on the right hand side, select ‘Add Rules’
• Choose ‘Blank Rule’
• Set Match Rule to:

Requested URL Matches the Pattern

Using Regular Expressions

Pattern: (.*)

Ignore Case: checked

• Set Action to:

Action Type: Rewrite

Rewrite URL: http://example.com:8080/{R:1}

Append query string: checked

• Stop processing of subsequent rules: checked

8. Now, with any luck – you should be able to access JIRA via http://jira.example.com  - if not, something isn’t set correctly.

Setting up Fisheye is almost as simple.

Say Fisheye is set up on http://example.com:8060 and I want to access it via http://fisheye.example.com

Repeat steps 4-8 above, substituting ‘fisheye’ for ‘jira’, and then verify you can access fisheye from http://fisheye.example.com

If you’re also doing .NET Development, or have .cs/.aspx/.asmx files in your repository, then you’ll also need to do the following.

Edit the web.config for fisheye.jira.com

Add the following to just before </system.webServer>

<handlers>
 <remove name="WebServiceHandlerFactory-ISAPI-2.0-64" />
 <remove name="WebServiceHandlerFactory-ISAPI-2.0" />
 <remove name="PageHandlerFactory-ISAPI-2.0" />
 <remove name="PageHandlerFactory-ISAPI-2.0-64" />
 <remove name="PageHandlerFactory-Integrated" />
 <remove name="WebServiceHandlerFactory-Integrated" />
 <remove name="SimpleHandlerFactory-ISAPI-2.0-64" />
 <remove name="SimpleHandlerFactory-ISAPI-2.0" />
 <remove name="SimpleHandlerFactory-Integrated" />
 <remove name="CGI-exe" />
 <remove name="ISAPI-dll" />
</handlers>
<staticContent>
 <mimeMap fileExtension=".cs" mimeType="text/plain" />
</staticContent>
<security>
 <requestFiltering>
  <fileExtensions>
   <remove fileExtension=".config" />
   <remove fileExtension=".csproj" />
   <remove fileExtension=".cs" />
   <add fileExtension=".cs" allowed="true" />
   <add fileExtension=".csproj" allowed="true" />
   <add fileExtension=".config" allowed="true" />
  </fileExtensions>
 </requestFiltering>
</security>

If there are any additional filetypes that are in your Fisheye repository that generate 404 errors when navigating, then add them to the fileExtensions section. First as a ‘Remove’, and then an ‘Add’ with allowed=true. You’ll also need to probably add a mimeMap entry too.

Thanks to @OhCrap for the pointers on enabling .cs serving with IIS7.