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Can't sync iPhone in iTunes anymore

iMac Mid 2011 running High Sierra Version 10.13.6

iTunes for Mac Version 12.8.3.1

iPhone 8 on IOS 14.5.1


When connecting my iPhone i get the message "A software update is required to connect to your iPhone" or words to that effect. I click Continue and a popup appears "Downloading 1 item" this stays for a good few minutes but then eventually, after about 20 minutes or so, fails with an error "Installation failed. Can't download the software because of a network problem."


Incidentally the same thing happens with my iPad Pro running IOS 14.4.2 only the first message is along the lines of "A software update is required to update your iPad". Both of them fail with the same network error when trying to download, what im assuming is an iTunes update?


My network is fine, im connected via Ethernet not Wi-Fi so there's no interruption to the internet. I've tried several times a day, at different times of day for about the past week and get the same error every time. When looking at Activity Monitor there are next to no packets coming in during this alleged download, 40 ish packets per second, data received about 8KB/s so there's clearly nothing downloading.

iMac 27″, macOS 10.13

Posted on May 17, 2021 2:48 AM

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Posted on May 20, 2021 2:11 AM

OK so it looks like i've fixed it. I booted the iMac in safe mode and plugged my phone in. Same thing happened as above, asked to download an update, stuck on Downloading.... with a full progress bar for about 10 minutes. But then eventually the progress bar emptied and it gave a minutes and seconds display of how long to download. It completed, updated iTunes, i rebooted in normal mode and iTunes can now connect to my iPhone.

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Question marked as Top-ranking reply

May 20, 2021 2:11 AM in response to Craig Southworth

OK so it looks like i've fixed it. I booted the iMac in safe mode and plugged my phone in. Same thing happened as above, asked to download an update, stuck on Downloading.... with a full progress bar for about 10 minutes. But then eventually the progress bar emptied and it gave a minutes and seconds display of how long to download. It completed, updated iTunes, i rebooted in normal mode and iTunes can now connect to my iPhone.

May 18, 2021 6:03 AM in response to Craig Southworth

Hey Craig, Thanks for posting your question about your software update issues in Apple Support Communities! A great place to start is by checking out your Wi-Fi settings and possibly restarting your router. Because the issue is happening with multiple devices and you are receiving almost identical error messages on both then it would point to an issue with your network. It may be best to try resetting your router and following the steps in the article: Recommended settings for Wi-Fi routers and access points, to properly configure its settings to work with Apple devices.


Best wishes.

May 20, 2021 12:21 AM in response to i_rina

I have tried rebooting the router and no joy. As mentioned earlier im on ethernet not wi-fi but even so both my wi-fi and my internet are solid as i work from home and my work laptop never drops connection to work servers or MS Teams chats etc. during the day. There's definately something wrong with the download. As the blue progress bar is full as soon as you hit Continue, but it just sits there saying "Downloading...." for about 20 minutes but then times out. It's almost like there's a corrupt cached version of the file that's partially downloaded perhaps? If i was able to delete the partially cached file it may force it to re-download from scratch?


When i say the issue is happening on multiple devices that's not strictly true. It's only the iMac trying to download the update that's the problem. My iPhone on IOS 14.5.1 will not sync to the iMac if i ignore the update. My iPad however, on IOS 14.4.2, can still sync with the iMac if i ignore the update. So itunes will sync with 14.4.2 but will not sync with 14.5.1 without an update, which is failing to download.


Also as a side note, iTunes on the iMac is able to download full Movies and TV Episodes that i have purchased without issue, thus further evidencing my connection is not the issue here.

Can't sync iPhone in iTunes anymore

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