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Calendar and Contacts in Outlook 2019 won't sync to my iPhone with iTunes 12.10.2

Hi everyone,


I know this may be an older issue, but I haven't yet found a definitive answer in the forums here or elsewhere online.


Does any know if it is possible to successfully sync Outlook's Contacts and Calendar from a PC to an iPhone? I am using an iPhone 8 Plus with OS 13.2.3, iTunes version 12.10.2.3, MS Outlook 2019 64-bit, and my PC is running MS Windows 10 Pro 64-bit version 1909, build 18363.476.


When I attempt to sync (from my PC to my phone only, which is what I have always done), iTunes says the Contacts and Calendar are syncing, but no actual data exchange occurs. Because of this, I have had to go back to my old laptop with MS Outlook 2010 and the same versions of iTunes & Windows.


I did see a previous short discussion similar to this issue, https://discussions.apple.com/thread/250629958, but the version of Outlook was older, and the initial problem was different.


I did try to contact Apple support via phone. They didn't understand what Outlook 2019 is, and were focused on the Outlook App instead. Then the nice support person asked a manager who told them that Outlook 2019 wasn't supported and that the issue is being worked on. Seems odd, since Outlook 2019 has been out for some time. I tried Apple Support via Twitter and I received a generic "Please follow us for news on updates.." response with was not helpful at all.


I would be grateful for any suggestions or assistance.


iPhone 8 Plus, iOS 13

Posted on Dec 6, 2019 7:00 PM

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Question marked as Best reply

Posted on Dec 6, 2019 7:50 PM

Update: IT WORKS NOW!!! It was a Windows driver issue, not an iTunes issue.


I rechecked the link I posted in the thread I started, and I decided to check my phone driver version within the Device Manager.


With my phone plugged into my computer, I looked for it in the Windows Device Manager. It was listed in the Universal Serial Bus Devices listed as Apple Mobile Device USB Device. I double-clicked on the device and the Driver tab to check the driver version, and it was some number starting with a 6.xxxx.xxx or something odd like that. For the heck of it, I clicked the Update Driver box, and had the computer search online (as opposed to on my computer) for an updated driver. Voila - it downloaded Apple Driver 423.36.0.0 (the one mentioned in the discussion thread I mentioned in my post) and installed it.


I restarted my computer, as I was prompted to after installation, and now there are 2 items listed in the Device Manager > Universal Serial Bus Devices section: the original Apple Mobile Device USB Device, and Apple Mobile Device USB Composite Device (above it).


I then tried to sync again, and all data transferred successfully without issue. Unfortunately, Windows had never updated with driver, despite being the most current version. I hope this helps other users with this syncing issue!

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1 reply
Question marked as Best reply

Dec 6, 2019 7:50 PM in response to IZ2019

Update: IT WORKS NOW!!! It was a Windows driver issue, not an iTunes issue.


I rechecked the link I posted in the thread I started, and I decided to check my phone driver version within the Device Manager.


With my phone plugged into my computer, I looked for it in the Windows Device Manager. It was listed in the Universal Serial Bus Devices listed as Apple Mobile Device USB Device. I double-clicked on the device and the Driver tab to check the driver version, and it was some number starting with a 6.xxxx.xxx or something odd like that. For the heck of it, I clicked the Update Driver box, and had the computer search online (as opposed to on my computer) for an updated driver. Voila - it downloaded Apple Driver 423.36.0.0 (the one mentioned in the discussion thread I mentioned in my post) and installed it.


I restarted my computer, as I was prompted to after installation, and now there are 2 items listed in the Device Manager > Universal Serial Bus Devices section: the original Apple Mobile Device USB Device, and Apple Mobile Device USB Composite Device (above it).


I then tried to sync again, and all data transferred successfully without issue. Unfortunately, Windows had never updated with driver, despite being the most current version. I hope this helps other users with this syncing issue!

Calendar and Contacts in Outlook 2019 won't sync to my iPhone with iTunes 12.10.2

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