Certificate trust policy not saving

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Level 1

5 points

Certificate trust policy not saving

macOS Monterey 12.5 on a M1 Mac Mini

When going to a website with a self-signed or untrusted certificate, I get challenged with "do you want to proceed", which is expected. I view the certificate by clicking "show certificate" and change the trust settings to "Always Trust", it asks me for a password to update the certificate trust, which completes. When I attempt to test the change by visiting the website, the process starts over and the certificate is once again not trusted. If I go into the keychain management directly and modify the trust settings to "always trust", I enter my password, go back in, and the trust settings are still at the defaults. It will not save my trust settings. I am an administrator. I tried deleting all certificates and then restoring them from iCloud.

I don't believe it's related to Safari - when I attempt to connect to a remote computer using Microsoft Remote Desktop for Mac, the same problem occurs. Up until 2-3 months ago, all of my remote connections/certificates were trusted and worked perfectly. I don't recall anything specific that changed, other than MacOS updates.

Any ideas?

Posted on Aug 11, 2022 4:52 PM

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Answer 1

Top-ranking reply

ryane77

Community Specialist

Aug 14, 2022 11:13 AM in response to bigpal

Hi bigpal,

Thanks for letting us know it happens in a new user. That tells you the issue is system-wide. Whether the issue would be resolved with restoring a Time Machine backup would depend on the date of the backup and the source of the issue, so we recommend testing it in safe mode as well. This helps to rule out a few potential software problems. Here's How to use safe mode on your Mac - Apple Support

"Safe mode prevents your Mac from loading certain software as it starts up, including login items, system extensions not required by macOS, and fonts not installed by macOS. It also does a basic check of your startup disk, similar to using First Aid in Disk Utility. And it deletes some system caches, including font caches and the kernel cache, which are automatically created again as needed.

Safe mode is particularly useful when you're trying to resolve an issue that doesn't seem to be associated with using any particular app. As always, keeping your software up to date is the first step toward resolving any software issue.

How to use safe mode

Determine whether you're using a Mac with Apple silicon, then follow the appropriate steps:

Apple silicon

Shut down your Mac.
Turn on your Mac and continue to press and hold the power button until you see the startup options window.
Select your startup disk, then press and hold the Shift key while clicking “Continue in Safe Mode.”
Log in to your Mac. You might be asked to log in again."

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Answer 2

bigpal Author

Level 1

5 points

Aug 14, 2022 8:25 AM in response to ASTRO24

I tested the same tasks with a new user account on the same computer, and I received the expected behavior (it works and the certificate stays trusted). Date and time are accurate.

If I restore from a time machine backup will I face the same problems?

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Answer 3

ASTRO24

Community Specialist

Aug 13, 2022 11:55 AM in response to bigpal

Hi bigpal,

Thanks for posting in Apple Communities.

We understand that you're experiencing trouble with the certificates when using Microsoft Remote. Start by placing your computer in safe mode and testing in a new user to see if this behavior continues. Check your time and date for accuracy.

If this behavior continues in safe mode or the new user, reach out to Apple Support to investigate this further.

Regards.

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Certificate trust policy not saving

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