Contacts and Calendars not syncing, missing items or creating numerous duplicates

Contacts and Calendars not syncing, missing items or creating numerous duplicates

  1. I have created numerous Apple support tickets on iCloud, iTunes, contacts, and calendar issues over the years without any resolution. Even the typical response from Apple’s technical support staff is often of a deer in the headlights, like they have never heard of the issue before. At the same time, I can find hundreds of threads on Apple, Google, and Microsoft forums, all leading down different rabbit holes and offering no solutions. The other standard response from Apple is that they cannot assist with third-party apps like Microsoft Office 365, and Microsoft, in turn, will ask us to contact Apple.
  2. For folks like me with a laptop with Windows 10, the problems are even worse. You have to deal with the iCloud app for Windows, the iTunes app for Windows, iCloud.com on the browser, and numerous settings in iOS on the iPhone to sync your contacts, calendars, etc. Even after messing with all of them, 90% of the time, they won’t sync. When I log in to iCloud.com on the Chrome browser on my laptop, the gear icon at the bottom left for showing Action items does not open up fully as with Microsoft Edge, so I can only use Edge.
  3. I have 15,805 contacts in my iPhone 13 Pro, made up of Yahoo 80, Outlook 3,303, iCloud 12,503, Att.net email 35, and Gmail 3,637. 90% of these contacts are duplicates. My notes for some of the contacts show up as new contacts; there are duplicate contacts with no information in any fields, etc. I dread searching for a contact because I have to look through 20 or 30 of them to find the correct phone numbers, emails, addresses, URLs, notes, etc. In other words, the iOS, which Steve Jobs created to simplify people’s lives and make us more productive, is instead sending us down rabbit holes 24/7. iCloud Contacts in Microsoft Outlook 365 is 12,829, which does not match iCloud contacts. I am unsure what the difference of 326 is.
  4. I noticed I am missing iCloud contacts that I added and saved on my iPhone. For a very important contact I exchanged several emails with over the past several weeks, I saved at least 15 minutes adding all her contact information details and saved it on my iPhone. However, she wasn't there when I tried to find her in my contacts on iCloud, Outlook 365, Yahoo, Gmail, etc.. Also, vice versa, if I add contacts in Outlook 365, they will not be added to my iPhone contacts.
  5. iCloud calendar issues are as numerous as iCloud contacts. Unlike Contacts, I have several color-coded Calendars in Outlook 365 for Gmail, iCloud, Outlook iCloud, etc. The only calendar that shows appointments is the iCloud one, which doesn’t match all the appointments on my iPhone 13 Pro, so I cannot rely on it to plan my day, for reminders, etc. Also, vice versa, if I add an appointment to the iCloud calendar in Outlook 365, it will not be added to the iCloud calendar on my iPhone or iPad. So, I am forced to add appointments only on my iOS devices.


Posted on Sep 25, 2023 10:50 PM

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3 replies

Oct 3, 2023 11:09 AM in response to Cowboys9909

Hello Cowboys9909,


Have you had a chance to work through these steps for any issues with security software: Resolve issues between iCloud for Windows or iTunes and third-party security software


Resolve issues between iCloud for Windows or iTunes and third-party security software

If you can’t open iCloud for Windows or iTunes, download content, sync your device, or use Home Sharing, your security software might be the cause. 

How to tell if your security software might be causing an issue

Security software created by companies other than Apple can prevent iCloud for Windows or iTunes from connecting to Apple servers or to devices. Sometimes, you might see a numeric error message when you sync, update, back up, or restore your device.

If your security software is causing an issue with iCloud for Windows

* You can't sign in with your Apple ID.
* You see "Verification Failed: An unknown error occurred" or "An error occurred during authentication. Please try again." 
* You see "Your setup couldn't start because your username or password is incorrect" or "Your setup couldn't be started because the iCloud server stopped responding."
* iCloud services won't update. 

If your security software is causing an issue with iTunes

* Your iPhone, iPad, or iPod touch aren't recognized in iTunes, or they won't back up, restore, update, sync, or activate.
* You see iTunes Errors 4, 6, 1630–1641, 3000–3999, or 9000–9999*.
* You can’t connect to iTunes Store to buy or download content.
* iTunes won’t open.
*If you see error 9006, your computer might not be able to connect to Apple servers or your iPhone, iPad, or iPod touch. Check for communication issues between iTunes and Apple software update servers. If you still see the error message, then continue reading to learn how to check your connectivity and security software.

Things to check first

Before you change your security software's setup: 

* Make sure that the date, time, and time zone are set correctly on your computer. Learn how to update these settings on a Mac or on a PC
* Log in to an administrative user account, not a guest account. Learn how to do this on a PC
* Update to the latest version of iCloud for Windows or update to the latest version of iTunes.
* Make sure that you have the latest software on your Mac or on your PC.
* Make sure that you set up Windows Hello. Learn how to set it up
* Make sure that you only have one type of security software installed. If you have more than one type of security software installed, you might experience performance issues.

Test your connectivity

1. Check your hosts file to make sure that it's not blocking iTunes from communicating with Apple's servers.
2. If you’re having issues using AirPlay, Home Sharing, iTunes, or Remote, test the connectivity between the computers or devices in your house. They should be connected to the same network and subnet in order to function properly.

Test your security software

If you still have trouble after you test your connectivity, your security software could be interfering with your computer's connection with iCloud for Windows or iTunes.

In some cases, it might be necessary to temporarily remove your security software to isolate an issue. Some Internet security apps don’t uninstall completely, so you might need to download and run a cleanup utility for your security software for it to be completely removed.

Work with your security software provider to allow the complete list of ports and services that Apple products use or if you need help with uninstalling their software.


It's also important to mention that you shouldn't use a VPN, as these can cause issues with the connection: Check VPN (Virtual Private Network) and third-party software to help resolve network connectivity issues


Let us know if that helps out.


Take care.

Oct 3, 2023 12:26 PM in response to destiny241

Thanks for

your reply. The recommendations above are NOT the solution to my issues.

Currently, I do not have any error messages while logging into iCloud or iTunes

on my Windows 10 pro laptop, so I know it's not any third-party apps that are

causing the problems. Also, I talked to Apple Support recently after creating a

ticket. They also walked through all my issues, and the only beneficial

assistance was the recommendation that I turn off the Automatic syncing of

calendars and contacts in iTunes, which they felt was creating duplicate

contacts.

Regarding

fixing the 12,000+ duplicates I have in iCloud, they only recommended doing it

manually. So, this will be a six-month or longer project for me unless I am

willing to spend 12 hours a day on it for two or three weeks. On the other

issues, with my calendars in Outlook not syncing with my iCloud calendar in my

iPhone 13 Pro and iPad, they recommended contacting Microsoft Office 365, for

which I pay an annual subscription of over $100. I have chatted with Microsoft

Outlook support for hours at a time. Their support staff in offshore locations

are of no help as they are not knowledgeable about these issues or give me a prompt

reply to contact Apple about my problems. So, I am in a Catch-22 with Apple and

Microsoft because their operating systems, apps, and software don't communicate.

Oct 12, 2023 12:38 PM in response to Cowboys9909

Hello Cowboys9909 and Apple Support,


I am wondering if I am experiencing the same issue. Just recently, I tried to sync my contacts from iTunes to Outlook 365 on my Lenovo laptop, running Windows 11 Pro. The only reason I was doing this is because I have a lot of duplicate contacts on my iPhone as well as alot of contacts that I can delete and I figured it was way easier to do this on the laptop than on my iPhone. Also, I was trying to clean up my Contacts in preparation for purchasing a new iPhone. I always cringe when I purchase a new iPhone because inevitably during the transfer of contacts from one phone to the next, the Contacts are never complete and almost always missing information.


Although I don't have as many Contacts as you, I do have over 2,000. I was horrified when after it was apparently completed, (which to be honest, I am not even sure if it worked) that the contacts on my iPhone are now all messed up. Information is missing, like phone numbers, emails, etc. I am literally distraught over this because I do not know if this info is gone for good or if it is somehow retrievable. And, all the contacts on my laptop in Outlook are also all messed up with information missing.


I have been searching ad nauseam trying to figure out if there is a way to retrieve all of my original contact info. If anyone has any suggestions, please advise.


Thanks so much.

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Contacts and Calendars not syncing, missing items or creating numerous duplicates

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