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

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! :)

2 answers

This widget could not be displayed.

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

This widget could not be displayed.

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.

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