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:

This process is successful for Confluence, redirecting:

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:

I have also tried the answer

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

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

Indeed i have set the proxyHost and proxyPort. This actually causes the instance on to display a "Service is running on an unknown port"

and display "500" errors in the gadget placeholders. Still displays "500" error.

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