Cannot drag and drop: "preparing to move to…" for ever - Dock does not show after cold booting Mac

There are a lot of old stuff installed in this mac - even stuff that mentions 10.7 or 10.4.

This suggests that you may have been upgrading in place year after year, OS after OS, for a long time.

It is very comfortable but at times a clean start can do wonders, since of all that old accumulated stuff there are bound to be things that break in systems that are several generations newer.

I recommend doing a full backup, preferably two; making an installer disk on a usb thumb drive; boot from that drive, erase the internal drive completely; install the OS, and then opt to migrate ONLY the user accounts.

EDITED - spelling error :-(

Very much agree with @Luis Sequeira1 approach and all the good advise including about Migrating Only the User Account.

Issues that may exist on the Time Machine Backup from Previous Installations will be migrated to the New Installation. This would badly pollute the new Original and Pristine installation of the new OS.

Scorched Earth Method 

This method will WIPE ALL Data and there is No Recovery - Period.

To perform this action will require booting from a Bootable Installer. 

The Bootable Installer can Only be performed on an Apple Computer 

This will have to be performed from a Qualifying Computer to run the version of macOS to be made on the Bootable Installer.

Example Only : Bootable Installer of Monterey would have to be done on a computer that Qualifies to run Monterey.

Notation: If the computer being used to perform this action is Too New or Too Old to qualify to run the version of macOS - this computer can not be used.

Alternative is, to gain access to a Qualifying Apple Computer from a family member, friend or associate.

Once that is done read on for preparing the Destination computer  >> Only works on Intel Based Apple Computers.

Extra Special Notation regarding the Touch ID equipped Apple Computer.

About Startup Security Utility and Must Enable from Recovery Mode the ability to boot from External Drive Before Attempting 

1 - Shutdown computer and disconnect all external drive Except the newly created Bootable Installer.

2- Restart and immediately hold the OPTION key until the Startup Manager appears and choose the USB Drive. 

3 - It will present options >> Disk Utilities >> View >> View ALL attached Drives. 

4 - Choose the Upper Most Drive ( not the volumes indented and list below ).

5 - The drive normally is called Apple Media or Apple SSD - that is the drive to Erase and format as APFS with the GUID Partition Map. This applies to macOS 10.14 Mojave and above. 

6 - Once that is done >> backup out of Disk Utilities and choose install macOS. 

7 - Follow the prompts and it may automatically reboot several time. 

8 - Upon a final reboot - Setup Assist will present with the newer version of macOS.

ApMaX wrote:

    /Applications/SpeedTools Utilities Pro/ATA Hi-Cap Driver/Hi-Cap Driver for MacOS X 10.4.x and Earlier/MacOS X 10.4.x and Earlier Hi-Cap Installer.app

    /Applications/LaCie Update Tool/LaCie Update Tool.app

        [Not Loaded] LaCieScsiType00.kext - com.LaCie.ScsiType00 (1.2.10)

    Flip4Mac WMV Plugin: 3.3.7.2 (? - installed 2015-12-25)

    DivX Web Player: 3.4.0.6 (? - installed 2015-09-16)

    2022-06-01 11:49:13 at.obdev.littlesnitch.networkextension05-21 08:42:57 lsd - Crash (4 times)

The above items are among those that I would certainly suspect as being the potential cause of some of your issues. Some of these are kernel extensions, which can interfere with normal MacOS functions. Speedtool Utilities, Flip4Mac, and DivX are outmoded and I would start by uninstalling all and then reinstalling with newer versions if the issues are gone. Little Snitch is known to be problematic; LaCie update tool -- what is that for, is it really needed (third party disk utilities have been endlessly problematic for many users).

Leaving things installed but turned off doesn't usually solve things as they have background processes taking up memory and resources that interact with other processes as long as they remain installed. You say you have "hundreds" ("thousands") of applications? Keep in mind that millions of users are running Monterey and never have those oddities with the dock, finder anomalies, etc. so something installed is conflicting. It's up to you, but the right approach has been suggested by Luis and by P. Phillips, namely start from a clean system and then install applications fresh. I have done this myself when moving to a new computer many times over the years and it took me no more than an hour or two. I certainly don't have "hundreds" or "thousands" of applications, however. It's up to you, of course; but in a future MacOS update, you may find that the issues multiply as you have items on there that date from 2014 and certainly are not functioning properly anymore. If you are using these Macs for something important, someone needs to take on a more systematic approach to maintaining the software, configuration, and systems.

Have you in fact booted into safe mode and tried to see if the anomalies are gone? That would be a more definitive test about an installation conflicting with something in the MacOS. Have you tried disconnecting all peripherals to see if the issues go away? As for deleting the dock plist, that is absolutely something worth trying; save the existing plist somewhere so you can move it back if that does not help. The fact that it seems to happen only 30% of the time points to something that may arise when certain parts of the disk are accessed or certain configurations of memory are reached, or certain peripherals are accessed.

I think things that have been installed in the past but are presently not loaded or running can affect how your Mac operates. Especially with the kexts that you have, along with scores of applications and software, some of which is so old as to probably not be fully functional or compatible with a modern MacOS. Others with more experience may chime in here to elaborate (or contradict me).

Your computer, with just the MacOS installed and nothing else, would not be behaving this way. Something you have installed, configured, or connected is causing this. If you can't or won't start over or try to eliminate some of those things that have been installed, you will probably have to live with what you have. With "hundreds" or "thousands" of applications installed, as you indicated earlier, it may take some time. Personally, in this instance, I would start from a freshly erased disk and install new packages in groups of ~ 4 at a time, and retest after each group for proper functionality. Alternatively, you can start to uninstall some packages to see if or when the issues go away. For each uninstall, the uninstaller needs to be complete and thorough to remove all the pieces. Just deleting the application is not enough.

Please run Etrecheck and post its full report here. Use the "additional text" button and paste the report into the text box.

There is almost certainly a software issue that is causing the Dock to become unresponsive in some circumstances.

The report may well lead us to the cause.

Very Heavily Modified System plus ClamXAV plus Cocktail Custom Shutdowns Routine which may a part to the Dock Issue.

Terminal command  killall Dock  and what happens.

ClamXAV - 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. 

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.

The The Built in Security  is all that is required to protect the computer.

As for Modification - anytime a system is heavily modified - there are sometime unintended consequences which may manifest itself with this computer issue

Hi ApMaX,

It sounds like you've already done some great troubleshooting here. What happens when you try to perform these tasks using a different user account on the Mac? If you're unfamiliar with creating one you can learn how here: Set up users, guests, and groups on Mac

Also, when reinstalling macOS did you format your drive prior to doing so? These answers will help narrow down what's causing the issue. We look forward to hearing back from you.

Take care.

There are several things that stand out in the report.

Major Issues:

Anything that appears on this list needs immediate attention.

Unsigned files - There are unsigned software files installed that could be malicious and should be reviewed.

Automatic updates disabled - Automatic updates are disabled. This computer is at risk of malware infection.

Security updates disabled - Security updates are disabled. This computer is at risk of malware infection.

Apple security disabled - Apple security software is disabled. This computer is at risk of malware infection.

Having security updates and SIP disabled is a risk that is not worth taking.

NOTE: security updates are separate from regular OS updates.

On the rare occasions when one might want to disable SIP temporarily, it should then again be reenabled.

You have clamxav installed. Third party "antivirus" are the source of only trouble and offer no additional security:

Effective defenses against malware and other threats

I strongly recommend that you uninstall clamxav and restore system security settings.

You have some other things that are not recommended.

Cocktail used to be useful, many generations ago; but now it is likely to cause trouble. Stuff like purging inactive memory should NEVER be done in any version of the OS since Mavericks. At best it hinders performance, at worst it can cause crashes.

You are running a vpn. Unless this is used to connect to a work or school network, as per their instructions, this is a security risk.

Public VPN are anything but private

Simple answer is who owners this computer ?

Who is responsible to maintaining , installing, uninstalling the Application appearing on this computer.

Below, are only a part of what is appearing in the Supplied EtreCheck Reported

Major Issues:

    Anything that appears on this list needs immediate attention. 

    Unsigned files - There are unsigned software files installed that could be malicious and should be reviewed.

    Automatic updates disabled - Automatic updates are disabled. This computer is at risk of malware infection.

    Security updates disabled - Security updates are disabled. This computer is at risk of malware infection.

    Apple security disabled - Apple security software is disabled. This computer is at risk of malware infection.

Minor Issues:

Unsigned files - There are unsigned software files installed. These files could be old, incompatible, and cause problems. They should be reviewed.

 System modifications - There are a large number of system modifications running in the background.

 iCloud Status: 7 pending files

Security:

Automatic Updates: Disabled

 Security Updates: Disabled

Antivirus software: ClamXAV

Unsigned Files:

    Launchd: /Library/LaunchAgents/com.maintain.Restart.plist

    Executable: /usr/bin/osascript -e 'delay 3' -e try -e 'do shell script "killall Cocktail"' -e 'end try' -e 'ignoring application responses' -e try -e 'tell application "System Events" to restart' -e 'end try' -e 'end ignoring'

   Launchd: /Library/LaunchAgents/com.maintain.ShutDown.plist

        Executable: /usr/bin/osascript -e 'delay 3' -e try -e 'do shell script "killall Cocktail"' -e 'end try' -e 'ignoring application responses' -e try -e 'tell application "System Events" to shut down' -e 'end try' -e 'end ignoring'

        Details: Exact match found in the legitimate list - probably OK

 Launchd: /Library/LaunchDaemons/com.maintain.CocktailScheduler.plist

        Executable: /usr/bin/osascript -e try -e 'set schedulerOwner to do shell script "defaults read /Library/'Application Support'/Cocktail/Scheduler.plist SchedulerOwner"' -e 'do shell script "users"' -e 'if the result contains schedulerOwner then' -e 'do shell script "/bin/sh /Library/'Application Support'/Cocktail/Scheduler.sh"' -e 'end if' -e 'end try'

        Details: Exact match found in the legitimate list - probably OK

Launchd: /Library/LaunchAgents/com.maintain.Sleep.plist

        Executable: /usr/bin/osascript -e 'delay 3' -e try -e 'do shell script "killall Cocktail"' -e 'end try' -e 'ignoring application responses' -e try -e 'tell application "System Events" to sleep' -e 'end try' -e 'end ignoring'

       Controller (2.0)

    /Library/Application Support/VPN Tracker 4

        [Not Loaded] NAT-T.kext - com.equinux.VPNTracker.kext.NAT-T (1.2)

    /Library/Application Support/VPN Tracker 5/lib

        [Not Loaded] VPNTrackerTiger.kext - com.equinux.VPNTracker (2.3)

  Launch Agents:

    [Not Loaded] com.maintain.Restart.plist (Not signed - installed 2022-05-09)

    [Not Loaded] com.maintain.ShutDown.plist (Not signed - installed 2022-05-09)

    [Not Loaded] com.maintain.Sleep.plist (Not signed - installed 2022-05-09)

Months?!!!

You are not reinstalling from floppies... but from the App Store or the developers' websites.

I always do a clean install when moving to a new OS (like from Big Sur to Monterey).

I takes me about a day, but the upshot is that I don't have stuff from 2014 causing trouble, and my mac works great...

Much like @ Luis Sequeira1 - have done Wipe and Install on macOSes over the years for various reasons with excellent results.

That said, it has taken about one hour with the USB Bootable Installer media in hand and then about 1 - 2 hours thereafter for the individual Applications to reinstall.

This is not an exclusivity to Microsoft Windows as it is implied earlier reply. Have done much the same in a Linux Installation too.

It is a considered opinion, there has been sufficient advise / suggestions offered, from more than One Source, for the User to make an informed and educated choice what the next course of action is required.

The suggestions have been put forth on a volunteer basis, in good faith and in the best interests of the computer.