I'm on a Mac (OS v.10.15.7) using Office 365 Outlook desktop application.
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That's interesting, Randy, though I'm always logged into Workfront so I wonder if there was some other way that it's recognizing it. Are you on PC or Mac?
On a Mac using Outlook 16.61 (365 subscription) and my default browser is Chrome 102.0.5005.61.
My SSO and direct login creds are saved in Chrome. My Workfront Add-in is v1.0.
That may be the difference. I know that if i log into WF via direct and then open a new tab and log in via SSO, Workfront logs me right in bypassing our SSO auth. I'm not sure if there's any connection between session ID and log in method.