Assisting an 87yr old getting music from older MacBook to newer iPhone

Question

Level 1

4 points

Assisting an 87yr old getting music from older MacBook to newer iPhone

I am helping a wonderful older lady transfer CDs to her iPhone. They are on a MacBook Air circa 2017? I am unsure of the exact date, but it's been too old to update to the current OS for at least a year.

Just a few months ago I was able to successfully plug in her iPhone, connect to iTunes and proceed with syncing the music of our choice.

Now when plugging in the iPhone I get prompted immediately that an update is needed. At first it was unclear what was being referenced so I updated the phone to iOS 18. Prompt still appeared so I attempted to update iTunes. The download either fails or stays stuck in progress.

What has changed in the last few months to no longer work? Are there any alternatives to transfer media from an older Mac to a semi-new iPhone?

Thank you so much!

Posted on Apr 14, 2025 1:46 PM

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Answer 1

Apr 14, 2025 2:31 PM in response to CostcoPizza

The update prompt is an update to Finder (or to iTunes, for older macOS versions), and is necessary for connecting to a particular iPhone or iPad.

The update will download in the background, and will apply itself to Finder (or iTunes).

The update is needed when the iPhone is not recognized by the built-in macOS software, which can happen after a macOS install, or after a substantial update or upgrade to macOS, or after an iOS or iPadOS update.

Here is what Apple states about this: If your Mac says that a software update is required to connect to iPhone or iPad - Apple Support

For completeness: The background update does sometimes — very rarely — get stuck too, and a reboot usually clears that.

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Answer 2

Phil0124

Level 10

210,841 points

Apr 14, 2025 1:56 PM in response to CostcoPizza

Any reason you did not simply accept the update when it appeared after plugging in the iPhone?

The update it requests is a firmware update. And it should apply from the pop up directly.

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Assisting an 87yr old getting music from older MacBook to newer iPhone