Solved: 535 5.7.139 Authentication unsuccessful, federated sts service was unreachable

Problem

535 5.7.139 Authentication unsuccessful, federated sts service was unreachable error message presented by Jira after integrating Microsoft 365 with Duo Single Sign-On.

Cause

Jira version that was used did not support modern authentication which was configured on Duo.

Solution

Upgrade Jira to a version that supports modern authentication

or

Configure the Microsoft 365 application within the Duo Admin Panel to enable the ‘WS-Trust’ feature

Supporting Documentation

What are the impacts of enabling modern authentication on the Microsoft 365 tenant

How do I enable and properly secure basic authentication for Microsoft 365 when federating with Duo SSO

Duo SSO for M365 Documentation

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