HTTP Proxy key keeps resetting in Keyring

Sure thing, tkhauser.

Let's see if you continue to notice this behavior in a new administrator account: Set up users, guests, and groups on Mac. If the issue is specific to one account, remove your login items with these steps:

• Choose Apple menu > System Preferences, then click Users & Groups.
• Click your account name below Current User, then click Login Items at the top of the window.
• Make a list of the login items—you’ll need to remember them later.
• Select all of the login items, then click the Remove button .
• Choose Apple menu > Restart.

If this solves the problem, open Users & Groups preferences again, add the login items one at a time, and restart your Mac after adding each one.

When the problem occurs again, follow the steps above to remove only the last login item you added.

If you don't have any login items or if removing them doesn't help, check to see if you have a configuration profile installed. The "View an installed configuration profile" section of this article will walk you through how to check for a configuration profile: Use configuration profiles to standardize settings on Mac computers

Reply to this message with your findings.

Take care.

Hi tkhauser,

Thank you for participating in the Apple Support Communities. It appears that you're having an issue with iCloud Keychain. First make sure your Mac is on the latest macOS version for the model: Apple security updates Then, make sure you're setting up iCloud Keychain with the steps outlined here: Set up iCloud Keychain

If the issue persists, start your Mac in safe mode and try setting it up again: Start up your Mac in safe mode

We hope that information is helpful.

Cheers!

tkhauser,

Thanks for replying with the steps you've tried and the results. We'd recommend reaching out to Apple for additional guidance. Reach them here: Get Support, or by calling the phone number listed for your region here: Contact Apple for support and service

Cheers!