Apple Support and Calendar issues .

Apple support has disconnected me because the automated system couldn't hear me saying yes to it's questions. It's happened twice. At the same time my Apple Calendar is different between my Mac, iPhone and the iCloud webpage. This is becoming very trying. Any thoughts on either of these problems?

Posted on Sep 21, 2026 8:24 AM

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Posted on Sep 21, 2026 8:36 AM

The obvious reasons why your Mac Calendar would not be synced are:

  • You have a VPN installed on your Mac or another network altering process that is preventing the sync. You can post the free EtreCheck report for your Mac and can be used to identify anything interfering or see iCloud processes that are hanging. The report contains no personal information.

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  • The Mac is not signed into the same Apple Account
  • Syncing for the iCloud Calendar is not turned on for the Mac at  > System Settings > [name on top] > iCloud > See All > iCloud Calendar.


As for getting Apple Support, I would suggest to try the Online Support option where you can use Chat Support instead. After you describe the issue, you will be given the related Support Articles and on the bottom of that page will be a link for "More Support Options". If Chat support is available in your region, then you will see a button to start that direct chat support.

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5 replies
Question marked as Top-ranking reply

Sep 21, 2026 8:36 AM in response to Chrisjohn06

The obvious reasons why your Mac Calendar would not be synced are:

  • You have a VPN installed on your Mac or another network altering process that is preventing the sync. You can post the free EtreCheck report for your Mac and can be used to identify anything interfering or see iCloud processes that are hanging. The report contains no personal information.

How to use the Add Text Feature When Post… - Apple Community

  • The Mac is not signed into the same Apple Account
  • Syncing for the iCloud Calendar is not turned on for the Mac at  > System Settings > [name on top] > iCloud > See All > iCloud Calendar.


As for getting Apple Support, I would suggest to try the Online Support option where you can use Chat Support instead. After you describe the issue, you will be given the related Support Articles and on the bottom of that page will be a link for "More Support Options". If Chat support is available in your region, then you will see a button to start that direct chat support.

Contact Apple Support - Apple Support


Sep 21, 2026 8:59 AM in response to Chrisjohn06

It is not just VPN's that would cause that, it is also other third party processes such as Little Snitch, Antivirus software, or a software Firewall, which is why I suggested using EtreCheck. You would want to look more closely at the Mac specifically if it is the Mac changes where you are not seeing the update on your iPhone/iCloud.


When you make Calendar changes on your iPhone, are those seen updated when viewing in iCloud? And if not, does it make a difference on whether you are using WiFi/Cellular on your iPhone.


If Apple has identified an issue, then certainly follow up with them. It is not something I am currently experiencing or seeing posts here for the same thing which would be expected in a system wide outage.

Sep 21, 2026 8:48 AM in response to Mac Jim ID

So I have no VPN on this Mac. Events show up on my Iphone, partially on my Mac, and I'm missing entire weeks on iCloud.com. Apparently their two support is seeing this situation across their services. They said to give it 4 more hours so I guess that 18 hours isn't long enough to synch to the web? I've always preferred Apple's security but this feels like low hanging fruit. I hope they get it worked out.

Apple Support and Calendar issues .

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