The Un-heavenly iCloud
If you are an Outlook user who wants to sync your contacts, tasks and calendars with your iOS devices using iCloud, you may have been frustrated with some of its… um, deficiencies. The primary issue is that iCloud moves all your contacts and calendar data into a special iCloud data folder which is not fully compatible with Outlook, resulting in a slew of difficulties.
The main problem, for me, was that any new appointments or contacts I would create did not get saved to the iCloud folder by default, so it was always an extra step to move them after creating them. And if I forgot, they didn’t get transferred to my iOS devices.
I also had problems with appointments, birthdays, and holidays randomly moving to different days–sometimes months from the actual date. I couldn’t trust anything on my calendar! And if I attached a reminder to an appointment, I would always get a warning about it not being supported for the folder, even though the reminder still worked–mostly. When using Outlook on the desktop, snoozing reminders saved in iCloud never worked properly. Another issue is that iCloud appointments were always set to a status of “busy” and then I would get warnings about schedule conflicts when there really weren’t any.
I, personally, never experienced any issues with contacts syncing through iCloud as long as I remembered to copy them to the iCloud data folder, but I know people who did have problems such as duplicate contacts and so on.
I put up with the aggravation of iCloud syncing for a year (with no improvements or bug fixes from Apple) because I hated dealing with iTunes syncing even more, and I didn’t want to have to remember to sync via iTunes daily to keep my contacts and calendar updated.
But recently, I learned you can sync your iOS devices with Microsoft Exchange. Actually, I knew this all along, but I thought Microsoft Exchange Server was a business service and that regular people like me could not use it. As it turns out, if you have a Hotmail, Windows Live, or Outlook.com account, you can use Microsoft Exchange to sync your contacts and calendar (but not tasks) with iOS! This article will explain how I switched from using the troublesome iCloud to using Microsoft Exchange for syncing my Outlook contacts and calendar with my iOS devices.
Create an Outlook.com Email Account
If you don’t already have a Hotmail, Windows Live, or Outlook.com account from Microsoft, you will need to create one by going to outlook.com. If you already have an older Hotmail account, you might want to go to outlook.com anyway and claim an address under the “live.com” or “outlook.com” domain. You do this by clicking the gear icon and choosing “More mail settings”. You can also create multiple Outlook aliases (up to 5 per month), a handy feature if you need extra email addresses for special purposes. But I’m getting off track…
(For simplicity, I am going to refer to the account as a Windows Live account throughout this article–it doesn’t matter if you created it with a live.com, hotmail.com, or outlook.com address.)
Get the Microsoft Office Outlook Hotmail Connector
Once you are set up with a Windows Live email account, you will need to download and install the Microsoft Office Outlook Hotmail Connector which allows Outlook to access the account.
Add the Windows Live Account to Outlook
After installing the Connector, you need to add the Windows Live Hotmail account to the desktop Outlook program. Once you do this, you will see a new data file in the left sidebar of Outlook with folders for each of your Windows Live email addresses as well as the other standard Outlook folders like Contacts, Calendars, Sent Items, etc.
Move the Items You Want to Sync from the iCloud Data File to the new Microsoft Data File
You’ll need to switch to the folders view in Outlook for this if you aren’t already there. Then you’ll need to move or copy all the items you want to sync from your iCloud data file to the corresponding folder for the Windows Live data file.
iCloud Contacts -> Windows Live Contacts
iCloud Calendar -> Windows Live Calendar
If you weren’t using iCloud already, then just move the items from their current locations to the corresponding folders in the Windows Live data file.
Note: Windows Live does not support sub-folders, so if you were using folders to create groups of contacts, you will not be able to keep them in separate folders if you move them to Windows Live. I don’t know of any workaround for this. If anyone does, please post a comment. Also, Windows Live does not sync tasks. If you need to sync tasks, you will need to create them as calendar events instead. Or, read the comments section after this article for some additional workaround suggestions.
Verify Your Data
If you already had a Windows Live account with data in these folders, you may need to do some clean-up after you move the iCloud data in. Outlook should handle duplicate contacts when you copy them, but you will have to look over your appointments to check for duplicates. For appointments, you’ll want to switch to list view and sort by name without grouping to make duplicates easy to spot. See how to remove duplicate imported items in Outlook if you need help.
I’d also suggest checking all your recurring appointments to ensure they have a correct recurrence pattern. You also might want to check the free/busy status for your appointments. I edited all of mine just to ensure I’d have no further issues like I was having with moving appointments. If you look at the screen shot below, you can tell which items came from the iCloud folder because the recurrence pattern will be in all caps. Once you edit them in Outlook, you will see the recurrence pattern in plain English and not all caps. Fortunately I had missed editing a few so I could show you this screen shot!
Assign Your Contacts to the Address Book
Now you probably want the contacts in your Windows Live account to be used for the Outlook address book when you click the “To” button while composing an email. To do that, right click the Contacts folder in the left sidebar, choose Properties, and then click the Outlook Address Book tab. If it’s not checked already, check the box for “Show this folder as an email address book.”
Change the Default Data File Location in Outlook
To make desktop Outlook save new contacts and appointments to your Windows Live account, you will need to change the default data file. But before you do this, you will want to make a backup copy of your Email Rules, because you’ll lose them when you switch default data files.
To backup Email Rules in Outlook 2010:
- Go to an email folder in the left sidebar.
- Choose Rules > Manage Rules & Alerts from the Home tab of the ribbon menu.
- Click Options, then “Export Rules.” Name the file and choose where to save it. Remember where you saved it so you can import it after changing the data file.
To change the default data file in Outlook 2010:
- Select the File tab of the ribbon menu. Click Account Settings > Account Settings to open the Account Settings box.
- Click the Data Files tab. You’ll see a list of all your data files here along with the path to where the actual file is saved on your computer’s file system. Since the Microsoft Live data is stored online it will show “Not Available” for the location.
- Click on this account name, then click “Set as Default.”
- Close the Account Settings screen.
- Go back to the “Manage Rules and Alerts” screen, and import the email rules that you just exported.
Now, you may be wondering why you couldn’t have set iCloud as the default data file before, when you were using iCloud to sync. Let me save you some trouble–if you do that, Outlook will refuse to open. If you already made this mistake and are stuck with Outlook not opening, you can fix it outside of Outlook by going to Control Panel > Mail > Data Files. Then change the default data file back to something other than iCloud.
Set Up a Microsoft Hotmail Account on Your iOS Devices
Whether you set up your account as Hotmail, Windows Live, or Outlook.com, it’s all the same. In iOS, you set it up as a Microsoft Hotmail account, no matter which extension you have for your email address. Apple has an article that describes how to do this: iOS: Hotmail, Live, or MSN email accounts. After setting it up, Apple refers to it as an Exchange account throughout iOS.
Once it’s set up, you can choose to sync one or all of the following: Mail, Contacts, Calendars, Reminders. (Although Reminders is shown as a sync option, it doesn’t actually sync with Tasks. This is a limitation of Windows Live.) Just turn on whatever you want to sync.
Repeat this for all the iOS devices you want to sync with your Windows Live data. The Microsoft Outlook Hotmail Connector will sync desktop Outlook with Windows Live, and your iOS devices will now also sync with Windows Live, so everything is kept in sync between desktop Outlook, Outlook.com on the web, and all your iOS devices.
Verify That the Microsoft Data is Syncing
Go back to Outlook on your desktop computer, and do Send/Receive. It might take a long time to finish the first time after you’ve added all your contacts and appointments. A few minutes after it completes processing in Outlook, you should see all the information start to appear in the respective apps on your iOS devices. In your Contacts and Calendar apps on iOS, you can go to groups and choose which data sources you want it to show. You will have groups for iCloud, Exchange, and possibly others, like Facebook. Since our goal is to do away with iCloud, you probably want to deselect that and only show information from Exchange.
You may want to do some tests, creating and editing dummy data in both Outlook and on your device(s) and checking that everything is syncing as you’d expect.
Disable iCloud Sync on Your Computer
Once you are satisfied that everything is syncing, you can open the iCloud Control Panel on your computer and uncheck the boxes to sync contacts and calendars. When you apply the changes, it will probably ask you to shut down and re-open Outlook. Go ahead and do that. If asked to keep the information on your PC, I think it’s best to leave it. I’d rather have duplicates than lose data.
Once you are confident everything is working correctly, you can either delete the contacts, etc. from your iCloud data file in Outlook, or simply close it. If you disabled all Outlook data from syncing with iCloud, your iCloud data file will be renamed in Outlook to “iCloud Archive.”
If you were already syncing your iOS devices with Outlook through iTunes instead of iCloud, you may want to disable that, too, so all your syncing will be over the air with Windows Live.
Disable iCloud Sync on Your iOS Devices
Finally, you have to go into the iCloud account under Settings > Mail, Contacts, Calendars on each of your iOS devices, and disable those items from syncing. Again, you will be asked to keep the data on the device or not. I chose to keep it, leaving it deselected in each app, knowing it will become outdated after some time. If you want to delete it later, you must do so through the iCloud.com web site.
That’s it. Now you can enjoy a more seamless sync experience between Outlook and your iOS devices. It seems like a lot of steps, but unless you have a big mess of duplicates or corrupted data, it doesn’t take all that long to set up.