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Set up Outlook to get email/calendars/contacts directly from the iCloud server, and also from your work server. On your computer, you should do the same. When you create a calendar event from the iPhone, you can even choose which calendar it belongs to. It will also allow you to show or hide each calendar separately, or simply see them both in the same calendar. Go through the active add-ins section and select 'iCloud outlook add-ins'. In the left panel, select the option of 'Add-ins'. for Outlook 2007 - Go to the tools section and choose trust center. Select the iCloud outlook add-in from the list. The iPhone will then overlay the calendar data from both accounts. Here, a pop-up window will appear, you only need to click on the 'add-ins' option in the left panel. Set up your iPhone in Mail/Calendar/Contacts settings to connect to your iCloud account, and then set up a second account to connect with your work's server (Exchange)? Your iPhone will then get calendar data right from the two source servers over the Internet (no more sync cables needed). Therefore, the solution to your configuration problem is simple. You iPhone is also capable of having multiple email/server accounts (i.e a connection to iCloud, another to your work server, and possibly another to a Gmail or Yahoo mail account). Instead, your iPhone is as capable as your computer to connect directly to your work server to exchange calendar data. These steps will work to add iCloud Calendar to Outlook 2013, Outlook 2010, Outlook 2007, and Outlook 2016.
HOW DO I SET UP ICLOUD IN OUTLOOK 2016 WINDOWS
Also, you’ll need an Apple account so you can sign into iCloud for Windows to do the iCloud Calendar Outlook setup.
HOW DO I SET UP ICLOUD IN OUTLOOK 2016 PC
Put simply, modern smartphones should rarely be "synched" with a computer any more to exchange data. Check to see if your Windows PC meets the minimum requirements for the software. The reason for this was simply that old Palm devices simply didn't have an Internet connection of their own like modern smartphones do. In this setup, the computer was the central repository of information. The pre-smartphone method of getting calendar data onto a phone (or the Palm Pilot's of the past) was to "sync" the device with a computer using a physical cable.
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I think that there is a better way for you to configure this to work smoothly for you.