macOS Platform single sign-on known issues and troubleshooting (preview)

Article
05/24/2024

This article outlines the current known issues and common questions with macOS Platform single sign-on (PSSO). It provides issue solutions and information on how to report an issue that isn't covered. This article also includes troubleshooting guidance.

Scenarios to validate

After deploying PSSO on your device, there are a few validation scenarios that you can do to ensure that the deployment is successful. If there are any issues, refer to report an issue for further instructions.

Password change events

Confirm that changes to Microsoft Entra ID password made through self-service password reset (SSPR) are successfully synchronized to the local machine. If a user's Microsoft Entra ID password changes after syncing it to the Mac, the user is prompted to enter their new password within 4 hours.

Repair or remove PSSO registration from a device

This section outlines how to repair or remove PSSO registration from a Mac device, depending on the macOS version.

macOS 14
macOS 13

On macOS 14 Sonoma, if there are problems with your device registration, you can repair the existing PSSO registration.

Open the Settings app and navigate to Users & Groups > Network Account Server.
Select Edit, then Repair. You're taken through the same device registration flow as when during your initial registration.

You can also deregister the device completely by doing the following steps.

Open the Company Portal app and navigate to Preferences.
To deregister the device, select Deregister.

Enterprise SSO plug-in does not activate after system update

If the Enterprise SSO plug-in fails to activate after system updates are applied to the device, you should reboot the software update daemon.

Open the Terminal app and enter the following command to kill the swcd process.
```
sudo killall swcd
```
Then enter the following command to reset the process.
```
sudo swcutil reset
```

Temporary passwords issued during password reset cannot be synced with Platform SSO

Temporary passwords issued during password reset cannot be synced to the local device. Users are advised to complete the password reset process using their temporary password using the SSO extension.

Device migration

Confirm that a previously registered device (with a Workplace Join key in Keychain Access) removes the key after successful PSSO device registration.

Frequently asked questions

Can I use macOS PSSO in a hybrid-join deployment?

No, macOS PSSO is only supported in Microsoft Entra join deployments. There are no plans to support hybrid-join deployments, as we recommend that Mac users go fully cloud based.

Known issues

Passcode policy complexity mismatches

There's a known issue where an applied MDM configuration specifies a local password policy with a higher degree of complexity than the Microsoft Entra account used to sign-in to the machine. In this case, the password synchronization operation between Microsoft Entra ID and the local machine fails.

Ensure during the MDM configuration that the password complexity requirements are identical between the local machine and Microsoft Entra ID.

If the device registration fails through the Settings application, the Device Registration popup will reappear after about 10 minutes, and you can try again.

SSO auth prompt dialog closed while the registration is in progress

If you cancel the registration process by closing the SSO auth prompt dialog, you need to sign out from your Mac device and sign in again. Upon a successful sign in, the registration notification reappears and works correctly.

Per user MFA causes password sync failure

If a user has per user MFA enabled on the account where PSSO is being set up, you won't be able to enter Microsoft Entra ID credentials in the next steps, causing an error. To avoid this error, admins should ensure they have Conditional Access MFA enabled in accordance with Microsoft Entra ID recommendations. This suppresses MFA during enrollment so that password synchronization can be completed successfully.

PSSO reregistration required after password reset initiated from FileVault recovery or MDM-driven recovery

Because Secure Enclave keys are protected by your local account password, password resets that occur without providing this password (such as FileVault or MDM-based recovery) will reset the Secure Enclave. Resetting the Secure Enclave renders keys previously stored for this account inaccessible. Devices whose Secure Enclave keys have been lost must be reregistered to use Platform SSO.

Report an issue

If you're experiencing issues with PSSO, you can report them on Company Portal.

Open the Company Portal app and navigate Help > Send diagnostic report.
A Send diagnostic report window appears. Select Email logs to send the logs.
Take note of your incident ID before closing the window.

You can check the current PSSO state on your machine at any time by opening the Terminal app. Run the following command.

Contact us

We'd love to hear your feedback. You should include the following information:

Apple logs

sudo log config --mode "level:debug,persist:debug" --subsystem com.apple.AppSSO"

Diagnostic data
```
sudo sysdiagnose
```
Steps to reproduce the issue
Where applicable, include relevant screenshots and/or recordings

Troubleshooting guide

Insufficient permissions

If a user has insufficient permissions to complete Microsoft Entra ID join and registration, no error message is shown. For the device join and registration to complete successfully, the user initiating the registration flow must be allowlisted.

In the Microsoft Entra admin center, navigate to Identity > Devices > Overview > Device Settings.
Under Microsoft Entra ID join and registration settings, ensure that the All option is selected in the toggle menu for Users may join devices to Microsoft Entra.
Select Save to apply the changes.

Troubleshoot Passkey issues

Platform Credential as Passkey option is only available if Secure Enclave is configured as the authentication method for Platform SSO. You should check the following:

Ensure that your admin has set up your device with Secure Enclave as the authentication method, and has enabled passkeys (FIDO2) for your organization.
As a user, check that you have enabled Company Portal as a passkey provider in your device settings. Navigate to your Settings app, Passwords and Password options, and ensure that Company Portal is enabled.

Troubleshoot Google Chrome SSO issues

If a user has the Microsoft Single Sign On extension for Google Chrome installed then their Chrome browser should be able communicate with the Microsoft SSO broker for both a SSO user experience and to work with device-based Conditional Access policies. If users are not able to pass device-based Conditional Access policies in Google Chrome then there may be an issue with how the Company Portal application was installed, which can prevent Chrome from communicating with the SSO broker. You should take the following steps to remediate this issue:

Open the Applications folder on the Mac
Right click the Company Portal application and choose Move to Trash
Download the latest version of the Company Portal installer from https://go.microsoft.com/fwlink/?linkid=853070
Freshly install Company Portal using the downloaded CompanyPortal-Installer.pkg

Validate that the issue has been resolved by checking for the existence of this file: ~/Library/Application\ Support/Google/Chrome/NativeMessagingHosts/com.microsoft.browsercore.json

ls ~/Library/Application\ Support/Google/Chrome/NativeMessagingHosts/com.microsoft.browsercore.json

Alternatively, you can deploy the following script via your MDM or other automation tools to copy the JSON file to the correct location. This script should be run in the the user's context for each user who experiences the Chrome SSO issue:

#!/usr/bin/env zsh
# Copy over Browser Core json file to the right location
# If the folder doesn't exist, create it

# For Google Chrome (user-specific, default path)

if [ ! -d ~/Library/Application\ Support/Google/Chrome/NativeMessagingHosts ]; then
  mkdir ~/Library/Application\ Support/Google/Chrome/NativeMessagingHosts
fi

cp /Applications/Company\ Portal.app/Contents/Resources/com.microsoft.browsercore.json ~/Library/Application\ Support/Google/Chrome/NativeMessagingHosts/

# For Edge (user-specific, default path, not channel specific)
# See: https://learn.microsoft.com/en-us/microsoft-edge/extensions-chromium/developer-guide/native-messaging?tabs=v3%2Cmacos

if [ ! -d ~/Library/Application\ Support/Microsoft\ Edge/NativeMessagingHosts ]; then
  mkdir ~/Library/Application\ Support/Microsoft\ Edge/NativeMessagingHosts
fi

cp /Applications/Company\ Portal.app/Contents/Resources/com.microsoft.browsercore.json ~/Library/Application\ Support/Microsoft\ Edge/NativeMessagingHosts/

Important

Note: This issue is due to a bug with how Company Portal is installed or updated under certain circumstances. This issue will be resolved in a future update to Company Portal.

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