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Preparing For macOS 12 Monterey or macOS Server for Monterey

Article ID = 262
Article Title = Preparing For macOS 12 Monterey or macOS Server for Monterey
Article Author(s) = Graham Needham (BH)
Article Created On = 4th May 2022
Article Last Updated = 4th September 2022
Article URL =

Article Brief Description:
A handy check list to do in preparing to install macOS 12 Monterey or macOS Server for Monterey

Preparing for macOS 12 Monterey and/or macOS Server (v5.12)

WARNING: As of 21st April 2022 OS X Server/macOS Server is no longer available as Apple has discontinued it.

Here is a check list to do before installing macOS 12 Monterey and/or macOS Server (v5.12):
  1. Check whether you have a compatible Mac from this list:
    • MacBook (Early 2016 or newer)
    • MacBook Air (Early 2015 or newer)
    • MacBook Pro 13"/15" (Early 2015 or newer)
    • Mac mini (Late 2014 or newer)
    • iMac (Late 2015 or newer)
    • iMac Pro (2017 or newer)
    • Mac Pro (Late 2013 or newer)
    NOTE: If you are not sure whether you have a compatible Mac check our macOS 12 Monterey Frequently Asked Questions article before proceeding.
  2. Monterey has a dedicated Signed System Volume - this means if you install it in the same APFS "container" as another version of macOS you will have issues booting. If you wish to install macOS Monterey on the same storage device as older versions of macOS (such as a dual boot configuration) you must create a new "container" (partition) for macOS Monterey and install it to that separate container/partition!
  3. Check you do not need any of the following as Monterey does not directly include/support them:
    • macOS 12 removes PHP - use Homebrew to install it or install via a third party software stack such as MAMP/MAMP PRO
    • macOS 12.3 and later removes support for kernel extensions used by Dropbox and Microsoft OneDrive - if you use these applications update to the latest versions before installing Monterey. Microsoft has in-depth information on their new "Files On-Demand" feature.
    • macOS 12.3 and later removes Python 2.x - use Python 3 instead (once macOS 12.3 is installed, run the stub /usr/bin/python3 in Terminal which will prompt you to install the latest Xcode developer tools that includes Python 3.x)
    • legacy System/Kernel Extensions (KEXTs) - no longer supported
    • VPN connections via L2TP over IPSec now require "HMAC-SHA-256" security at the third-party server end - make sure your VPN server is compatible!
    • 32-Bit Applications - no longer supported
    • Legacy media formats - no longer supported
    • TLS certificates signed with the SHA-1 hash algorithm - no longer supported
    • Apple's hardware RAID and Apple's RAID Utility - application removed
    • Installing on and booting from FireWire storage - no longer supported
    • .safariextz packaged Safari Extensions - Safari 14 in Monterey does not support them
    • Legacy NPAPI browser plug-ins including Adobe Flash - Safari 14 in Monterey does not support them
    • Playlist XML files - Monterey splits iTunes into separate applications but also removes support for Playlist XML files - many popular DJ applications no longer work in Monterey and will need to be upgraded
    • The Dashboard feature - it is no longer available in the Mission Control System Preferences
    • Legacy smart card support that uses TokenD - no longer supported
    • The ability to run AppleScripts/use Scripting Additions - see this in-depth article
    • The ability to run most server features in macOS Server
    • The ability to fully run applications that utilise OpenGL
    • Back To My Mac - no longer supported
    • Proxy Automatic Configuration (PAC) via FTP or File URL schemes - no longer supported
    • Messages support for AIM, Yahoo, Googla Talk and Jabber accounts - no longer supported
    • PPTP VPN - no longer supported
    • Rosetta for running PowerPC software - no longer supported
    • Web Sharing - no longer included
    • Xgrid Sharing - no longer included
    • X11 - XQuartz may need to be reinstalled if you use it
  4. If you have a third party SSD installed in your computer check to see if it needs a firmware update before installing Monterey.
  5. Make sure you are connected to the internet (preferably with a fast connection and with a large or no data cap in place).
  6. Make sure you have an Apple ID (use the iTunes or App Store application to create one if necessary e.g. go to Macintosh HD > Applications > App Store > Store menu > "Create Account…" to get started if you don't have an Apple ID).
  7. Consider whether you want the Mac App Store Apple ID to be the same for services such as iCloud, iTunes, etc if you are going to use them.
  8. Check you have enough disk space:
    • macOS 12 Monterey installer = ~12.5GB
    • macOS Server 5.12 installer = ~100MB
    • macOS 12 Monterey installation (from OS X 10.9.5 Mavericks, OS X 10.10 Yosemite, or OS X 10.11 El Capitan) = ~44GB
    • macOS 12 Monterey installation (from macOS 10.12 Sierra or later) = ~26GB
    • macOS Server 5.12 installation = ~250MB
  9. Backup and/or clone your computer.
  10. Check that your favourite software is Monterey compatible.
  11. Temporarily disable any third party disk encryption software.
  12. Temporarily disable any anti-virus/malware software.

Article Keywords: macOS 12 Monterey 1200 macOS Server 5.12 OS X OSXserver512

This article is © MacStrategy » a trading name of Burning Helix. As an Amazon Associate, employees of MacStrategy's holding company (Burning Helix sro) may earn from qualifying purchases. Apple, the Apple logo, and Mac are trademarks of Apple Inc., registered in the U.S. and other countries. App Store is a service mark of Apple Inc.

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