iTunes cannot read the content of the iPhone...

Hi blmatthews,

We'll be glad to help you.

You can find steps to take, depending on the error code being seen, outlined here: Find an iTunes or Finder error code - Apple Support

If the iPhone is not being seen by the computer, these steps from If your computer doesn't recognize your iPhone or iPad - Apple Support may help:

1. Look in the Finder or iTunes

On a Mac with macOS Catalina or later, look for your device in the sidebar of any window in the Finder.*

On a Mac with an earlier version of macOS, look for your device in iTunes.

On a PC with iTunes for Windows, look for your device in iTunes.

Learn more about viewing your device in the Finder or iTunes

2. Update the software on all devices

Update your iPhone or iPad

Update your Mac

Update your Windows PC

On your PC you might also need to update iTunes and update drivers.

3. Connect your device directly to your computer

Make sure that your device is unlocked and showing its Home Screen, then use a USB cable to connect it directly to your computer. Don't connect to a USB hub, display, or other device. 

If that doesn't help, disconnect your device and all other USB devices and accessories from your computer. Then reconnect only your device. 

4. Trust your computer, if asked

If you see a “Trust this Computer?” alert on your device when you plug it into your computer, tap Trust.

About the 'Trust This Computer' alert

5. Allow the accessory to connect

When connecting your device to a Mac laptop computer with Apple silicon, your Mac might ask whether you want to allow this accessory to connect. If so, allow it to connect.

Learn about allowing accessories to connect

6. Restart your devices

Restart your iPhone

Restart your iPad

Restart your Mac

Restart your Windows PC

7. Try a different port, cable, or computer

The issue could be related to your computer, its USB port, or the USB cable connecting it to your device. If possible, try a different computer, USB port, or USB cable. Also check for any debris in the charging port on the bottom of your iPhone or iPad.

8. Contact us

If your computer still doesn't recognize your iPhone or iPad, contact Apple Support.

We hope this helps you.

Cheers.

blmatthews,

Let's try to narrow this down and isolate it more by testing in safe mode and a new user account. Safe mode prevents certain software from opening and completes great checks on startup. More information on starting to safe mode and steps to take after starting there can be found in the link below. 

How to use safe mode on your Mac - Apple Support

Please determine whether you're using a Mac with Apple silicon.

Apple silicon

1. Shut down your Mac.

2. Turn on your Mac and continue to press and hold the power button until you see the startup options window.

3. Select your startup disk, then press and hold the Shift key while clicking “Continue in Safe Mode”.

4. Log in to your Mac. You may be asked to log in again.

Intel processor

1. Turn on or restart your Mac, then immediately press and hold the Shift key as your Mac starts up.

2. Release the key when you see the login window, then log in to your Mac. 

3. You may be asked to log in again. On either the first or second login window, you should see "Safe Boot" in the top right-hand corner of the window."

If the prompt continues to show after the steps from safe mode, create a new user account (administrator) to see if the behavior happens there. This will let us know if it is system-wide or something within your user account: Change Users & Groups settings on Mac

Please let us know the outcome after giving the above steps a try.

Cheers!

Thanks for replying, blmatthews, and that additional info. Since you have updated to macOS Monterey, you would use Finder to manage and sync the iPhone: Use the Finder to sync your iPhone, iPad, or iPod touch with your Mac - Apple Support

If you are still having an issue, please contact Apple directly for further support: Get Support

Have a great day and thanks for using the Apple Support Communities!

Hello blmatthews,

Thanks for that info. The issue might be related to your computer, its USB port, or the USB cable connecting it to your device. If possible, try a different computer, USB port, or USB cable. Also check for any debris in the charging port on the bottom of your iPhone or iPad. Make sure the cable are Apple Official cables too.

If you still can't find a resolution, please contact Apple Support to sign into this further with you.

Thanks.