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Jira with Azure AD Application Proxy Edited


We're having some issues with a specific setup where we use Azure AD Application Proxy to allow all users to access the Jira site without VPN by first logging into Azure AD.

  1. Users browse to
  2. User is prompted to login to Azure AD
  3. User is forwarded to Jira
  4. User can login to Jira or access company "public" data without logging in to Jira itself (they would not be able to access Jira without logging into the proxy, so we have confirmed they are employees).

This all works fine except for some specific cases.

  • Gadgets on dashboards have their titles/configuration to say _MSG_Gadget_... because Jira accesses itself to fill these in
  • REST API calls to Jira (from within Jira via groovy scripts) fail as they use the Base URL which points to as they are prompted to login (I think this is the problem)
  • Possibly other issues regarding the system making calls to itself

The Azure Proxy is setup as follows: (external URL) directs to the proxy which directs to jira.mysite.internal (Internal URL) which points to the IP of the server. All users should access the Jira via the and not use the internal URL.

Is there a way to tell Jira not to go to but directly to itself as in the IP address to load gadgets, and all the other cool stuff?

I tried changing the /etc/hosts file on Linux to point to the IP address of itself, but that doesn't seem to do anything for the gadgets.

Anyone have experience with this or an idea of how to approach this?

Thanks in advance8

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