Apple usually rolls out a new version of their operating system every fall. This year is no exception, and the company released macOS version 12 named Monterrey on Monday, October 25, 2021. Many users will want to install Monterey to take advantage of its new features. 

The OS update is free and under normal circumstances should be installed without any issues. But as with everything else, there is always the chance something goes wrong and you lose some data. We are going to show you how to recover deleted files if you run into problems with your Monterey upgrade.

What Is macOS Monterey?

What Is macOS Monterey

Monterey is the latest version of the macOS and continues Apple’s practice of naming their operating systems after iconic California landscapes. While it’s not as extensive of an update as last year’s Big Sur, many new features make it a worthwhile upgrade. 

Here’s a brief list of what you will find in macOS Monterey:

  • Upgrades to the FaceTime app include the ability to share your screen with SharePlay and new microphone modes for better sound quality;
  • Upgraded Messages application that makes it easier to use Messages when using another app;
  • Newly designed Safari interface that is more immersive and customizable;
  • New Quick Note feature to allow you to jot down ideas no matter what you are doing on your Mac; 
  • Enhanced privacy features to keep your personal information more secure.

This is just a sampling of what’s inside macOS Monterey.For more details on what’s inside the Monterey upgrade, consult this Apple support page.

Common issues with updating to macOS Monterey

While the majority of users will not have any problems installing Monterey, unexpected issues can occur during any operating system upgrade. Following are some of the most common issues that may impact your ability to successfully upgrade and can result in lost or deleted files and folders.

  • 🚫 Running out of free space – When you open the Software Update panel in System Preferences, the amount of free space necessary to perform the upgrade is displayed. Make sure that you have at least this much free space available on your system. I would recommend having at least twice as much as indicated to make sure the installation doesn’t fail due to lack of storage space.
  • ⚠️ Losing power during the upgrade – You should always make sure you have enough power to complete the OS upgrade once it is started. This means you should probably avoid running on battery power if you have a MacBook. But even if you are plugged in, there is always the chance of a random power hit or failure. If this happened during installation, the process will fail and you may end up with some lost files.
  • 🔣 Faulty upgrade code – Apple strives to make sure that its operating system upgrades have been fully tested. Most times, there will not be any problems with the installation and your system will be fine when it is finished. If you do experience any issues that result in lost files, we have some solutions for you later in this article. You should reach out to Apple support if you experience problems that indicate a bad update file is being used for the upgrade.

How to safely update your Mac to macOS Monterey

It’s always a good idea to take a few extra precautions when performing a major operating system upgrade. By following the steps outlined below, you have a great chance of a successful upgrade that enables you to take advantage of the new features of Monterey. 

Check your Mac or MacBook to ensure it is compatible with the new OS. Older Macs may not have enough power to efficiently run Monterey, and installing it on those machines is not recommended. Most Macs built after 2015 can run Monterrey. You can verify that your computer can handle Monterey by consulting this Apple support page.

Though not a requirement for upgrading your OS, it is strongly recommended that you make a backup off your Mac using Time Machine or another solution of your choice before proceeding with the process. As we will see shortly, it may be just what you need to recover files that get inadvertently lost or deleted during the upgrade. 

The installer may run into a space problem if there is not enough free space available on your Mac. If this is the case, you can free up space using native features of macOS or third-party tools. Once you have enough space for the installation, you can continue.

Open System Preferences and click on Software Update. Click the Upgrade Now button and the OS will begin its upgrade process. Leave your computer alone while the installation proceeded. Your Mac may restart several times during the upgrade. Be prepared to enter your administrator credentials if necessary.

upgrade macos to monterey

When the installation is complete, your Mac should be ready to use with the new features introduced by Monterey. 

More information on upgrading to macOS Monterey can be found on this Apple support page.

How to Recover Lost Files After macOS Monterey Update

Now let’s look at several techniques you can use to recover files that are lost or accidentally deleted after an update to macOS Monterey. We’ll start with a simple recovery method that is available as a feature of macOS. This should always be the first method you try when a file or folder goes missing on your Mac.

Method 1. Recovering from the macOS Trash

Whenever you are faced with a lost or deleted file on a macOS system, the first place you should look is in the Trash. This special system folder stores recently deleted items for 30 days or until you manually empty the Trash. Here’s how to see if your lost files are in the Trash.

  1. Open the Trash by clicking on its icon.
  2. Search for files or folders that you want to recover.
  3. Right-click on the item you want to retrieve and select Put Back to recover it to its original location.put back files from trash bin monterey

Method 2. Restore from a Time Machine backup on Mac

Time Machine is the native Mac backup and recovery tool and comes installed with macOS. You should be taking advantage of Time Machine to protect your valuable data by taking backups regularly. As mentioned in the section on updating your Mac, you should definitely create a backup before upgrading the operating system. 

If you experience any data loss after your upgrading your OS to Monterey, use the following procedure to recover the files and folders using a Time Machine backup.

  1. Connect the external disk or other storage media that contains the Time Machine backup to your Mac or MacBook.
  2. Open a Finder window in the folder that previously stored the files or folders that are missing.
  3. Launch Time Machine by clicking the clock icon located on the Menu bar.enter time machine on macos monterey
  4. Scroll through the backup using Time Machine’s controls and locate the items you want to retrieve.
  5. Choose the files you want to recover and preview them if you wish by pressing the Space Bar.
  6. Click Restore to complete the recovery. The items will be recovered to their original locations on your Mac.restore files with time machine

Method 3. Recover deleted files using another backup solution

Perhaps you use a different backup method to protect your important data. Many options can be used to back up your data to a local device or the cloud. Let’s look at how to get your lost files back if you have stored them in iCloud.

  1. Go to and sign in with your account credentials.
  2. Click on Settings.go to icloud account settings
  3. Click on the Restore Files option located under the Advanced tab on the bottom-left of the window. click restore files
  4. Locate the files you want to restore and check the boxes to the left of their names. You can also Select All to get everything available at once.restore files from icloud
  5. Click on Restore Files.

Other online solutions like Dropbox and Google Drive have unique characteristics that need to be taken into consideration when performing a restore. The following are general steps that are appropriate for just about any type of recovery procedure.

  1. Connect to the physical device or cloud storage service storing your backups.
  2. Find the files you want to retrieve using the tools navigation features. 
  3. Choose the files you wish to recover and a safe place to restore them on your Mac.
  4. Complete the recovery using the tool’s interface.recovery files from cloud backup solution

Method 4. Recover lost files after a macOS Monterey update with data recovery software

If using backup media fails, you may be able to recover lost files from a Monterey update with data recovery software. The software will scan your internal disks for deleted files and give you the opportunity to recover them to a safe location. 

There are many data recovery applications available on the market. We like to use Disk Drill for several reasons. It has a nice interface that makes it easy to use, employs powerful scanning algorithms to find all your lost files, and includes free tools to protect and manage your valuable data.

Use the following procedure to use Disk Drill to recover files out when upgrading to Monterey.

  1. Download and install Disk Drill for Mac. Don’t perform the download and installation on your main drive, as that is where the lost files are located and you can accidentally overwrite them, making it impossible for the software to recover them. We suggest using an external hard drive or USB stick to protect your data.install disk drill for mac os monterey
  2. Launch the app and select the disk or partition that contained the lost files.
  3. Click the Search for lost data button to begin scanning the device for recoverable items. start scan your drive with disk drill
  4. Review the list of items found by Disk Drill and preview them if you wish. Choose the files you want to found items
  5. Click the Recover button to start the recovery process. You will be prompted to select a safe storage location to store the recovered data. Choose a location that is not on the same disk or partition you are files and recover them
  6. Click OK to complete the recovery.Select recovery path and recover


In most cases, you won’t have any issues upgrading a compatible Mac or MacBook to Monterey. If you do happen to lose some files, the methods described above should help you get them back. Take our advice and backup your machine before going ahead with the upgrade. It will take a few minutes but will be well worth the time if you end up with a problem during the upgrade. That being said, happy upgrading and good luck!


Robert Agar

Robert Agar, a dedicated data recovery writer, has been a pivotal part of the CleverFiles team for over 6 years. Before this, he enriched IBM for 13 years as a Backup and Recovery: TSM Subject Matter Expert. A proud alumn...

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Approved by
Brett Johnson

This article has been approved by Brett Johnson, Data Recovery Engineer at ACE Data Recovery. Brett has a Bachelor's Degree in Computer Systems and Network, 12 years of experience.