Solving problems syncing your Apple stuff to iCloud


Update 2015. The current Mac OS 10.12 uses slightly different methods to manage iCloud although this post is not being updated. The concepts captured here will educate you enough to get the job done.

Here are some of the most common problems people have when syncing accounts to iCloud.

The easiest way to think of The cloud is to imagine a large connected disk drive attached to your computer. All your documents, music, pictures and other stuff can be stored there. But this special disk only allows access with the proper credentials. If you don’t know the password and user name you don’t get access. If there is no internet, there is also no cloud. Once you grasp this concept the rest starts to fall into place.

Apple’s flavor of cloud computing works best with Apple products and contains “built-ins” that take much of the guesswork out for you. Ideal because most Mac owners have other Apple devices that should carry the same information across them. The most likely items you’re trying to sync are contacts, calendars or documents. If you use suggestions in this guide, keep in mind that it can take a little time for things to sort out once you make a change so if you know you have all the settings correct and are still having problems, wait a quarter hour or so before checking your efforts. If it absolutely is not working after following this guide, contact Apple Support for iCloud, or give Denver Mac a call.

How to test your iCloud services.

These instructions are written for Mac users, PC users will find resources on related sites.


Most problems can be resolved by fixing these.

For iCloud, settings consist of having the iCloud services turned on,

choosing which items to sync, and

using the same credentials among each device.

For our example we will be syncing calendars between a device called your Mac and a second device called iCloud which lives far away from you and gets accessed through the internet using safari, chrome Firefox, etc.

Start with your Mac. System Preferences > iCloud. Items that you want to sync should be checked on in the list (see illustration).

A valid iCloud account shows a name under the iCloud icon. In the picture below, it is shown  as “Your Account.” If there is no name that appears under the iCloud icon you’re not signed into iCloud, click Sign In and enter the email address you have registered with Apple. You’ll need to enter the password as well. The login name and password you will use is the same as that used with other Services you subscribe to from Apple like iTunes or Apple ID. (



Paramount to iCloud syncing is iCloud itself. iCloud is a device just like your iphone or Mac – as far as syncng is concerned.

We have to test if items chosen to sync from one device aligns to the other. Here its a device your phone, and device 2 the icloud you see in your browser. We only want these  two things: One device signed into, and showing in a web browser.

So now we know that iCloud itself is a device and that makes troubleshooting easier. We are only testing between two devices; your mac and iCloud living in your browser. To access iCloud go to

From the list of apps in iCloud choose calendar or contacts.

Now head back to your test machine’s contacts or calendars app, which ever you chose earlier and create the new test file. Title it test and don’t worry about filling everything in, a name will do, then save and close the event or contact.

Now head back to your test device browser pointed to icloud and watch. It may take a few minutes for things to upload, there are progress indicators while the sync takes place.

Understand that when you enable iCloud, your space on Apple’s cloud servers becomes active. That active space is the core of your cloud. Devices don’t sync to each other, they all get their information from iCloud, its the middleman in the process where the new item gets pushed and pulled through the internet to and from your devices.



If it was successful you should see the test item in your browser looking at iCloud. It is your home master. Adding or deleting information from sync’d items in your Mac should reflect in iCloud from your web browser and visa versa. Test going the other way, create a new contact or calendar in the web browser. You can delete the test file in any place and it should reflect at the other end. Changes should get updated across your first two synced devices – Mac and iCloud. If this doesn’t happen, don’t go any further until this crucial step gets resolved.

And as already mentioned, make sure all your devices are connected to the internet. WIFI or phone band work as long as nothing between your device and the internet such as a firewall or router is blocking access.


Now to add a second device to your cloud sync. Here, we’re going to add an iPhone to the mix. The pictures below are what the settings look like on iPhone running IOS 5. The top graphic shows the list of settings. Choose iCloud and that takes you to the second window. The most important item is at the top of the second graphic – Account. You need to sign into iCloud on the new device with the same credentials used with your first device. Now choose what you would like to sync on the second device. In the example below just about everything is turned on except Photo Stream and Documents & Data.




We will need to look for messages from iCloud after we turn the sync on. There might be contacts or calendar events that do not match up with what iCloud holds from our first device and iCloud will both warn us and give options for syncing. Again it is best to choose merge when adding new devices to your iCloud but you’ll need to think things through because your case may be different. For example you may have built the bulk of your contacts or calendar entries on your phone instead of your Mac. You may have separate mail accounts on different phones or some other uniqueness that will need thought before you start clicking the options iCloud gives when adding accounts. Just think it through before making decisions and it will with good likelyhood work itself out after a few hours.

Continue adding devices using the same process outlined here until all of your devices are included. Now giving a little time for the syncing to catch up with all your devices, you should enjoy cloud computing Apple style.

Some problems we have seen in iCloud syncing and how to fix them:

Families sometimes share a Mac between them but have separate iCloud accounts: Set up separate User accounts on the Mac using each person’s iCloud account assigned to each new Mac account.

After syncing to iCloud, entries in Calendar and Contacts get double entered: Turn iCloud off in each device. Clean up calendars and contacts on the devices. Then turn on iCloud again to delete duplicates. See this Apple Tech article for more information on deleting duplicate iCal entries:  And also here:


We will add more here as it become available.

(c) Denver Macintosh 2012 – 2015