What to do when iTunes prompts you to update when connecting an iPhone

A newer version of iOS can require a small software update for iTunes that isn’t otherwise available.

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Apple generally tries to explain itself when it prompts you to download a file, install an update, or otherwise take an option. Readers have suggested the company has fallen down in a prompt that appears in the following set of circumstances, in which all are true:

  • You’re using iTunes in Mojave or earlier in macOS.

  • Your iPhone or iPad is running a version of iOS or iPadOS released in a year later than the macOS version (i.e., Mojave and iOS 14, or High Sierra and iOS/iPadOS 13 or later).

  • You connect your phone to your Mac via a USB cable.

iTunes may prompt with a dialog that reads, “A software update is required to connect to your iPhone.” It offers three buttons: Learn More, Not Now, and Install. Some readers and forum posters have found clicking Learn More leads them to learn exactly nothing more, as no page appears.

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Apple could make this dialog much clearer.

This has led some people to worry that clicking Install will start the Catalina installation process, given that they are running an out-of-date version of macOS. It will not, fortunately, but I can understand the concern.

The explanation could be clearer. iTunes lacks some component requires to interact with iOS 14 or iPadOS 14, and it has to download a file that requires an installation process, not just a simple download, which it could perform in the background (one might think).

The dialog should more accurately read, “Your version of iTunes requires a software update to connect to your iPhone with iOS 14 installed.”

In some cases, people have found that clicking Install and following prompts has not worked. In that case, you should quit iTunes and disconnect your iPhone or iPad and then launch iTunes and plug in your device again. If that fails, your next resort should to perform a normal restart of your phone or tablet and your computer.

This Mac 911 article is in response to a question submitted by Macworld reader Bill.

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