Error "500 - Internal server error." when accessing Jira through IIS 7 Url Rewrite Reverse Proxy

[Stephen Dcruz]

Recently I have been trying to set up a URL Rewrite using IIS7 and URL Rewrite 2.0 to rewrite the URL:
http://jira.example.com.au:8081
to
http://jira.example.com.au

This process is successful for Confluence, redirecting:
http://confluence.example.com.au:8090
to
http://confluence.example.com.au

The jira website does respond, and will even go as far to append the /secure/dashboard to the redirected URL.
It then however displays the message

Server Error
500 - Internal server error.
There is a problem with the resource you are looking for, and it cannot be displayed.


Now I have tried to use the following links:
https://answers.atlassian.com/questions/28873/configure-iis-to-forward-requests-to-confluence-along-with-jira-subdomain

https://confluence.atlassian.com/display/JIRA044/Integrating+JIRA+with+IIS

https://confluence.atlassian.com/display/JIRA044/Integrating+JIRA+with+Apache

https://confluence.atlassian.com/display/JIRA/Configuring+Apache+Reverse+Proxy+Using+the+AJP+Protocol

I have also tried the answer
https://confluence.atlassian.com/display/JIRAKB/Integrating+JIRA+with+IIS+using+ARR

But also to no avail.

I have also tried using the AJP connection, unsuccessfully mind you.

I know it is redirecting correctly (since confluence works well) but i cant find any setting i can change to allow these requests to go through to jira.

Please help! :)

[Stephen Dcruz]

Indeed i have set the proxyHost and proxyPort. This actually causes the instance on http://jira.example.com.au:8081 to display a "Service is running on an unknown port"

and display "500" errors in the gadget placeholders.

http://jira.example.com.au Still displays "500" error.

[JamieA]

Have you set the proxyHost and proxyPort in the server.xml? What is the stack trace in the server logs?