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I am running macOS 10.14.6 and trying to connect an iPhone running iOS 14.3

It shows the message: "A software update is required to connect to <phone>" with a link to https://support.apple.com/HT208831

Unfortunately nothing on that page or the internet in general tells me what the update actually is. Is this a patch, an iTunes update, or a full operating system update? I'm cautious because I can't yet upgrade beyond macOS 10.14 (I have several 32-bit applications which I still need).

If I install this update, will it update me to 10.15 / 11?

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That Apple page reads, in part:

If your iPhone, iPad, or iPod touch has a newer version of iOS than is supported by your Mac, you may see this alert: "A software update is required to connect to your iOS device. Would you like to download and install this update now?"

Click Install to download and install the software so your Mac can update or sync your iOS device. If you continue to see this alert, make sure that your software on your Mac and iTunes are up-to-date.

All this does is install software on your Mac which allows macOS (usually an older version) to work with a new version of iOS on your iPhone. As for which specific software is updated (system files and/or iTunes) I do not know, but this update will not update your Mac to a newer version of the operating system.

I saw this window pop up after I'd updated my iPhone 8 to the latest iOS some weeks ago. My iMac is still running Mojave because of some 32/64 bit app incompatibilities.

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Got the above mentioned message

A software update is required to connect to your iPhone

while connecting an iPhone to a Mac running macOS Catalina 10.15.7.

I used fswatch to monitor disk activity during download and installation.

The download had the ID 052-14079 to which I could not find any official reference.

The downloaded files were (possibly among others):

/Library/Updates/052-14079/052-14079.en_GB.dist
/Library/Updates/052-14079/052-14079.en_GB.extraInfo
/Library/Updates/052-14079/CoreTypes.pkg
/Library/Updates/052-14079/MobileDeviceOnDemand.pkg

I made a copy of MobileDeviceOnDemand.pkg before it was removed but noticed CoreTypes.pkg only later on.

I extracted MobileDeviceOnDemand.pkg with Pacifist.

The binary executable files (possibly among others):

/System/Library/PrivateFrameworks/RemotePairing.framework/Versions/A/RemotePairing
/System/Library/PrivateFrameworks/RemotePairing.framework/Versions/A/Resources/bin/RemotePairingDataVaultHelper
/System/Library/PrivateFrameworks/RemotePairing.framework/Versions/A/XPCServices/remotepairingd.xpc/Contents/MacOS/remotepairingd
/System/Library/PrivateFrameworks/AirTrafficHost.framework/Versions/A/AirTrafficHost
/System/Library/PrivateFrameworks/DeviceLink.framework/Versions/A/DeviceLink
/System/Library/PrivateFrameworks/Mercury.framework/Versions/A/Mercury
/System/Library/PrivateFrameworks/MobileDevice.framework/Versions/A/MobileDevice
/System/Library/PrivateFrameworks/MobileDevice.framework/Versions/A/AppleMobileDeviceHelper.app/Contents/MacOS/AppleMobileDeviceHelper
/System/Library/PrivateFrameworks/MobileDevice.framework/Versions/A/AppleMobileDeviceHelper.app/Contents/Resources/MDCrashReportTool
/System/Library/PrivateFrameworks/MobileDevice.framework/Versions/A/AppleMobileDeviceHelper.app/Contents/Resources/AppleMobileBackup
/System/Library/PrivateFrameworks/MobileDevice.framework/Versions/A/Resources/MobileDeviceUpdater.app/Contents/MacOS/MobileDeviceUpdater
/System/Library/PrivateFrameworks/MobileDevice.framework/Versions/A/Resources/usbmuxd
/System/Library/PrivateFrameworks/MobileDevice.framework/Versions/A/AppleMobileSync.app/Contents/MacOS/AppleMobileSync
/System/Library/PrivateFrameworks/MobileDevice.framework/Versions/A/XPCServices/MDRemoteServiceSupport.xpc/Contents/MacOS/MDRemoteServiceSupport
/System/Library/PrivateFrameworks/MobileDevice.framework/Versions/A/XPCServices/MDPrivilegedUSBSupport.xpc/Contents/MacOS/MDPrivilegedUSBSupport

After the update connecting the iPhone and creating a local backup worked.

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I have a solution that has actually WORKED.

2011 MacBook Pro running updated macOS Catalina and an iPhone XR running updated iOS 16. I was flummoxed by two different flavors of "a software update is required to connect to your iPhone" and two different flavors of "installation failed/cannot install the update file" along with "iPhone could not be read".

Went through just about every suggestion out there, including installing Xcode, reinstalling iTunes (now just called Music), clearing caches and so forth.

MY solution? Time and Date. Yep. I come from starting with 8086 PCs back in the 80s and one key thing that fouled folks like me up with preventing computers actually FUNCTIONING AT ALL - time and date were not properly set to match what the computers was communicating with. In today's world, time and date issues basically can't really stop a computer device (everything is one, now) from functioning but they can sure throw a wrench in the works and cause lots of headaches.

I pulled up the time and date in my iPhone, which showed that I had the time set in 24 hour format (being military/fire-rescue in my past life, that's a habit) AND, while "Set automatically" was turned on, the Time Zone field just had a SPINNING WHEEL and nothing else.

I turned the 24-hour format OFF, making the time read in the usual am/pm format, which matched that of my MBP time and date. And guess what happened?

The spinning wheel in the Time Zone field disappeared and was replaced with "Cupertino".

Reconnecting the iPhone to my MBP, I DID get the messages that the contents of the phone could not be read and that a software update was needed to connect the iPhone to the manager. I ran the software install, which actually COMPLETED. I did get one message about reading the phone, but...dismissing that EVERYTHING HAS BEEN WORKING AS IT SHOULD!

Boiled down: make sure your TIME AND DATE SETTINGS ARE THE SAME between your Mac/MacBook and your devices.

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