MacOS 12.6.6 Unstable

None of that is normal…

Install EtreCheck and post the report. Allow Full Disk Access.

https://etrecheck.com/

Use the Additional Text icon to paste in the report.

Something may reveal itself in the report.

Update

I went through Apple-> About This Mac -> Storage and found very large (170GB) of system files. I went ahead and deleted a few apps and large media files. VOILA - suddenly Finder shows 260+GB free space like before the 12.6.6 upgrade.

That allowed me to download EtreCheck and run a report -- I'll attach it once I can get Word or Pages or Text Edit or any app to load.

The scary part is that it says my hard drive is failing. But I don't know how to interpret the details of that section of the report. I'd really appreciate opinions from people here who could give a sense of how bad the drive really is.

Depending on the outcome of the Monterey 12.6.7 update with the Safari 16.5.1 included.

Do a strong " Shack-down " aka Test if the original issue is still presented

If so, run a New Etrecheck Report and post back the results with Full Disk Access.

There is no use working from an Old Report since newer version of macOS was installed

FYI: Monterey version 12.6.7 was released today (June 21 '23) with a Safari version 16.5.1 update as well.

Took a look at your EtreCheck report. You have some software installed I'm not familiar with. The items listed under "Minor Issues" may not be so minor. I would wait for other replies but if it were my iMac, I would back up my data, erase the drive and start over with a fresh install of Monterey.

Just to add, among others I have a Late 2015 27" 5k iMac running Monterey 12.6.6 and have none of the issues you mention.

A really fast look but will look deeper tomorrow

/Library/LaunchAgents/com.mcafee.McAfeeSafariHost.plist

    /Library/Application Support/McAfee/MSS/Applications/McAfeeSafariHost.app/Contents/MacOS/McAfeeSafariHost

To add to previous suggestion from @BDAqua

There are no known Windows-like Viruses in the wild that self replicate and affect macOS, because of the underling UNIX  Foundation and Permission Limitation. 

Starting in macOS 11 Big Sur and above. 

The Operating System resides in a Sealed and Read Only Volume that can not be opened by the User nor by Third Party Applications.

The only Entity that can open and modify or alter this Volume is Apple.

That would occur when a update or UpGrade is performed.

The Only thing this Antivirus software is protecting is the Bank Account of the Developers and for zero return to the User aside from the problems this software creates.

AntiVirus Developers purposefully Market their product to create a “ Fear Factor “. In so doing, creating a False Need for their Product.

Third Party Security Software 

This will include BitDefender , 

This will included Norton Antivirus 

 Sophos Av Software

Intego AntiVirus

 McAfee, 

➡️ Avast AntiVirus

Ad Guard,

 Webroot ,

 ESET ,

 Avira ,

AVG AntiVirus  

➡️ avira antivirus 

Trustee  

AntiVirus for Mac

F-Secure

Securemac

Cylance

Kaspersky Internet Security

Total Virus Software 

Read some of the posting and arrive at your own conclusions.

The The Built in Security  is all that is required.

If as you say, Google Chrome is the Only remaining issue.

You may want to explore removing it completely including the somewhat outdated keystone aspect listed below

Re-download a more current version and then Test

Q-   [Loaded] com.google.keystone.agent.plist (Google LLC - installed 2022-10-27)

    Command: /Library/Google/GoogleSoftwareUpdate/GoogleSoftwareUpdate.bundle/Contents/Resources/GoogleSoftwareUpdateAgent.app/Contents/MacOS/GoogleSoftwareUpdateAgent -runMode ifneeded

Holy cow... Antivirus software: Avira, Avast!

Uninstall those 2, but I've never seen them Properly remove all their files, so I'dd recommend...

https://nektony.com/mac-app-cleaner

Hopefully that gets rid of the VPN thing also.

ExtreCheck full access report attached.

Now it no longer mentions problems with the hard drive -- just that disk space is low.

If the user wants a more detailed analysis of the Report - suggest re-running the Application with Full Disk Access

We are willing to give it a go and offer some suggestions

Below is from the Limited Permissions Report above

" Limited permissions - More information may be available with Full Disk Access. "

Interesting as running the Terminal command below

  softwareupdate --list-full-installers

Finding available software

Software Update found the following full installers:

p.phillips@Ps-Mac-Mini-M1 ~ % 

>> It will find but not list all available updates for Big Sur, Monterey or Ventura <<

Ventura 13.4 is what I am running presently

In the Ventura case, the System Setting >> Software Update Applet will and does present the 13.4.1 update

The last time I saw this behaviour was when running the Ventura 13.3.1 and Apple released the 13.3.1(a) Rapid Response update

Follow On and update

Apple security updates - Apple Support (CA)

EDITED

Final update. I was finally able to upgrade to Monterey 12.6.7 and Safari 16.5.1 I re-ran EtreCheck and everything seems to OK now except one note about proxies.

Suggestions welcomed.