I saw this while testing earlier. Still investigating, but figured I would list the steps that preceded getting the prompt. Note that I was testing migration to JC3 and SS+ on a working endpoint with JC 2.45.1. All testing was done on a known working local account that was successfully synced via JC. Config profiles were deployed, one for com.jamf.connect.login and one for com.jamf.connect)

1. Updated from JC 2.45.1 to JC 3.1.0. All good so far.

2 Pushed out SS+ (2.4.0) for a test drive. The JC integration was active in Self Service+ along with the Menubar still showing with company branded icon.

3. Uninstalled JC using the uninstaller and then reinstalled JC 3.1.0. Wanted to see the results if installing JC from scratch. The JC Login Window worked but no JC Menubar nor integration within SS+.

4. I then ran the SS+(2.4.0) installer once again. Boom! Keychain popup triggered. Once I authenticated with the local account password and selected “always allow” I once again had a working JC MenuBar and JC integration with SS+.

I'm wondering if the attempted creation of a new user state plist (com.jamf.connect.state.plist) is what is triggering the prompt? 

I’ll add that Self Service+ is setup as the default app to install (Self Service classic is no longer getting deployed on newly imaged machines). There is no required login to the Self Service+ app.

The keychain prompt appears 15-20 seconds after first login and to get the Onboarding window to show up you have to open the Self Service+ app manually.

Jamf Pro Cloud Version: 11.18.0-t1750091520803

I’ve enabled Self Service+ and macOS Onboarding to launch and install software immediately after user login, but unfortunately, macOS Onboarding doesn’t launch.

If anyone knows a solution, please help me out.