Why am I ALWAYS asked if Apple Support Communities can trust my iMac?

Are you by any chance clearing cookies and website data between visits?

Or using Private browsing mode?

In either case, the trust cookie would be deleted, and it would ask for it again since it cannot find it.

If you want to have it remember the setting, don't delete the website data and / or don't use Private browsing mode.

System Integrity Protection is disabled, so what’s actually installed here is unclear.

Given LittleSnitch, TechTools, MalwareBytes, Objective-See firewall, some other apps, and all sorts of signature errors, I’d reinstall this Mac.

Get a backup, get another backup, erase and install, and migrate over files and docs and not apps.

Add-on security apps have a habit of getting tangled, and of blocking operations that would ordinarily work.

I’d also recommend ensuring regular backups too, as storage corruptions can also arise from failing storage.

After logging into the Apple forums and "Trusting" your Mac, sign out & quit the whole browser. Launch the browser again and log into the Apple forums, did it retain your "Trust" setting? If you must still get a code & trust it again, the repeat the steps, but this time after quitting the browser, reboot the Mac before trying to log into the Apple forums.

The purpose here, is to make sure the "Trust" setting is retained by flushing the cache to the drive. I have lost "saved" data & settings if an app crashes even days later afterwards, so I believe the cache may not be written to the drive in a timely manner. I find this also happens a lot with apps utilizing a database for storing settings.

Try using a different browser to see if the issue is just with Safari, or occurs with any browser.

If the issue only occurs with Safari, then you may want to delete all browser cookies associated with "apple.com" & try again.

I’ll assume you’re using the iMac 21.5” from the footer, and not wandering among networks.

Other causes can include add-on apps, including add-on VPN clients.

Please download and run EtreCheck, and share the report to the clipboard. Then open a new reply here, and press the Additional Text button that looks like a printed page to get a text input box big enough to paste the hardware and software configuration report here, and paste and post it here.

HWTech wrote:

The purpose here, is to make sure the "Trust" setting is retained by flushing the cache to the drive. I have lost "saved" data & settings if an app crashes even days later afterwards, so I believe the cache may not be written to the drive in a timely manner. I find this also happens a lot with apps utilizing a database for storing settings.

I’ve seen similar, and suspect a transient cache-skewing or timing bug somewhere deep within NSUserDefaults. Or within iCloud sync. Where feasible, switching the setting to “the other setting”, waiting a minute or so, and restarting, and then re-setting as preferred, usually clears that.

If you're regularly deleting cookies, that can cause what you're seeing.

The first things I'd try disabling are Little Snitch, Malwarebytes and anything by Intego.

They are certainly less frequently implicated in issues that say, CleanMyMac but, as I suspect their might be some "phoning home" involved, seems as if they could be. A longshot, perhaps. If turning them off does nothing, turn them back on.

Personally, I download Malwarebytes about once a year, run the free version, find nothing and delete it. I've never seen the need to have it installed permanently. When troubleshooting, I tend to look at things that, from my perspective and experience, there's no clear need for and start by taking those out of the equation. Your perspective may be very different.

That is a ANCIENT version of EtreCheck. Compard to current versions, it reveals very little data. Please get the latest version by following the Update window:

or by going directly to the Etresoft home page:

https://etrecheck.com/en/welcome.html

The current version is free unless you want to unlock some advanced features not needed at this time.

There is so much unneeded third-party goop on that computer that I'm surprised it works at all.

• Smith-micro sofware is useless "protection" and needs to go.
• You have an old adware threat, noted by a SIMBL file. See: https://www.thesafemac.com/arg-conduit/#more-1295
• Micromat has not been required by OSX since long before High Sierra was released. It became largely redundant around macOS 10.5. I've not used or needed it in years since I got my first Intel Mac is 2008.
• Same redundacy with DiskWarrior. Great old tool, but not for High Sierra,
• Silverlight was deprecated years ago.

The list could go on, and on...

A good guideline: If you use it, update it; if not, dump it.