I use a Win7 PC with iCloud and Outlook 2010 for syncing my calendar and contacts. I can enter data in my Outlook Calendar and it will appear in iCloud, but data entered in iCloud does not sync back to Outlook. ICloud syncs to my iphone fine both ways.

Question

I use Win 7 PC with iCloud and Outlook 2010 for syncing my Contacts and Calendar.  They have stopped syncing...mostly.
Now, appointments I enter on my local Outlook (iCloud) Calendar goes up to iCloud fine.  But, data I enter on iCloud directly does not come down to my local Outlook iCloud Calendar.  If I reboot the computer, the iCloud data shows up.
Also, Contacts I try to enter on my Outlook (iCloud) Contacts goes up to iCloud fine, but does not show up in my local iCloud Contacts.
All syncing works with my iPhone.
I have signed out of iCloud on PC.  I have stopped syncing and re-started.  No change.
I have an .aplzod folder for iCloud.  I have a separate Earthlink.net.pst email account in Outlook and a me.com.pst Outlook email account (which I don't actually use) listed under Data Files.
Any help would be appreciated.  Curious that Outlook will upload to iCloud but not receive downloads unless I reboot.  However, rebooting does not download the missing Contacts.
Jim Robbins

Answer 1

Hi Jim!
You've started off with some good troubleshooting steps, so let's see if we can take this a little further and figure out what the issue is with your iCloud contacts and calendars. I have two articles here that will help you troubleshoot this issue a little further, but the troubleshooting steps for both articles are exactly the same, so I will lay those out for you here:
Note: When using iCloud Control Panel 2.0 and later, iCloud Calendar event descriptions in Outlook 2010 do not support text formatting (bold, italics, or underline), HTML, images, or attachments. The contextual (right-click) menu has also been disabled.
If you are having trouble with a PC (with Outlook 2007 or 2010) and iCloud Calendar, try each of these steps, testing after each to see if the issue is resolved:
Verify that you are using a Windows configuration that is supported by iCloud. For more information, see iCloud system requirements.
When enabling Calendars in the iCloud Control Panel, part of the setup process is to copy your Calendars data from the default Outlook ".pst" file to iCloud, and then remove the Calendars from the ".pst" file by placing them in the Deleted Items folder in Outlook. The Calendars data is then stored in the iCloud data set within Outlook so that changes can be pushed to and from Outlook by iCloud. Be sure you are looking for your data within the iCloud dataset within Outlook after enabling Calendars in the iCloud Control Panel. The deleted files can be seen by viewing Deleted Items within your Outlook Folder List. This is not iCloud removing your data; iCloud simply copies your data into the iCloud data set and then removes the local Calendars data by placing it in the Deleted Items folder.
Make sure your computer is online. Attempt to view www.apple.com and iCloud.com. If you can't connect to the Internet, your iCloud calendars and events will not update in Outlook. Click here for more information about troubleshooting your Internet connection.
Open a secure website to test if you are online as is necessary for iCloud Calendar. This also tests if the ports 80 and 443 are accessible. Outlook requires port 443 access to iCloud in order to push and pull updates to and from the iCloud Calendar servers.
Verify that your iCloud member name is entered into the iCloud Control Panel pane. See iCloud Setup for more information about setting up iCloud on Windows.
Completely close and reopen the iCloud Control Panel.
If you recently made changes in Outlook and they are not moving to your other devices or vice-versa, click the Refresh button in Outlook.
Turn iCloud Calendar off and back on:
Close Outlook.
Open the Windows Control Panel:
In Windows 8, move the pointer to the upper-right corner of the screen to show the Charms bar, click the Search charm, and then click the iCloud Control Panel on the left.
In Windows 7 and Vista, choose Start menu > All Programs > iCloud > iCloud.
Remove the checkmark in the checkbox next to Mail, Contacts, Calendars & Tasks, and click Apply. Wait a few seconds, then replace the checkmark, and click Apply.
Open Outlook and test to see if the issue has been resolved.
Ensure the iCloud Outlook Add-in is active within Outlook.
Outlook 2010:
Open Outlook 2010.
Click the File menu.
Click Options in the left panel of the Outlook window.
Click Add-Ins in the left panel of the Outlook Options window.
Look at the list of add-ins beneath "Active Application Add-Ins" and verify that the "iCloud Outlook Add-in" is listed.
For Outlook 2007, follow these steps to verify the iCloud Outlook Add-in is active
Open Outlook 2007.
From the Tools menu, choose Trust Center.
Select Add-ins from the left column.
Look at the list of add-ins beneath "Active Application Add-Ins" and verify that the "iCloud Outlook Add-in" is listed.
For additional information about managing Add-ins with Microsoft Outlook, see this Microsoft support document.
Restart your computer. This may sound simple, but it does reinitialize your network and application settings and can frequently resolve issues.
iCloud: Troubleshooting iCloud Contacts
http://support.apple.com/kb/ts3998
iCloud: Troubleshooting iCloud Calendar
http://support.apple.com/kb/ts3999
Thanks for using the Apple Support Communities!
Cheers,
Braden