Hi @Scott ,
Thanks for reaching out! Since you mentioned you’re working within a school environment, I wanted to first suggest checking out the Google for Education Community. It's a great resource for industry-specific setups like yours.
In the meantime, here are a few steps to help troubleshoot your Smoothwall certificate issue:
1. Verify Admin Console Settings
Navigate to Devices > Networks > Certificates and ensure the following:
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The Smoothwall Root CA is uploaded and assigned to the correct Organizational Unit (OU).
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The certificate is pushed to both the User OU and the Device OU.
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Ensure the checkbox "Use this certificate as an HTTPS certificate authority" is selected.
2. Run a Local Device Check
On an affected Chromebook, go to chrome://settings/certificates and select the Authorities tab. Search for "Smoothwall."
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If it’s listed: The certificate synced successfully. The issue may lie with your Smoothwall decryption policy or a date/time mismatch on the device.
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If it’s missing: The device hasn’t pulled the latest settings. Navigate to chrome://policy, click Reload Policies, and check if the OpenNetworkConfiguration policy contains the certificate blob.
If these steps don't resolve the issue, I highly recommend posting your query in the Google for EDU Community. You'll be able to connect with other admins who use Smoothwall in similar environments.
Best of luck!