Symptoms

While running Bitbucket Server connected to JIRA User Directory, it is not possible to clone nor push in the following combination:

git clone http://username@bitbucket:7990/scm/ACME/acmerepo.git

Diagnosis

To simulate the request that Bitbucket Server is making to JIRA and see what JIRA is returning: 

1. Create a file named "post-data" with the following contents:

   <?xml version="1.0" encoding="UTF-8" standalone="yes"?>
   <password>
   <value></value>
   </password>

2. Run the following cURL command (from the directory where the file was created) with <application-name> and <application-password> replaced with the application name and application password that Bitbucket Server is using to connect to JIRA as a user directory:

   curl -v -X POST -H "Accept: application/xml" -H "Content-Type: application/xml" -u <application-name>:<application-password> https://www.acme.com/jira/rest/usermanagement/1/authentication?username=bbunny --data @post-data

3. If JIRA is integrated with IIS, the response should contain something like:

   Server: Microsoft-IIS/7.5
   ...
   X-Powered-By: ASP.NET

Cause

JIRA uses a 400 response code with a specific message in the body to indicate to Bitbucket Server that authentication for a particular user has failed. In this case the response body and content-type are being mangled by IIS behavior.

This causes Bitbucket Server to mis-parse the response from JIRA and fall over with a 500 error on the client.

Resolution

• Edit the web.config system.webServer section and set httpErrors existingResponse attribute to "PassThrough":

  <system.webServer>
      ...
      <httpErrors existingResponse="PassThrough"></httpErrors>
      ...
  </system.webServer>

  For more information check Integrating JIRA with IIS.