How to sync your Outlook calendar with an iPhone

With the addition of Touch Bar functionality to Outlook, Windows and iOS devices are now more compatible than ever! That’s great news for professionals who need to balance between Microsoft and Apple in their daily workflow, but it also raises a lot of content issues. One of the most common is the problem of juggling different calendars on different platforms. While Outlook will happily update its own calendar automatically based on emails and team data, that doesn’t really help if you tend to pull out an iPhone to create dates or reminders when on the go. If you have an iPhone 7 and a PC, this can be a hassle.

The solution is cross-platform syncing, and yes, it is available for Outlook and iPhones. Here’s what to do!

Note: Some syncing services may be a bit different depending on the version of Outlook or iTunes that you have. Follow the general path and you should still get the same outcome. 

Step 1: Connect your iPhone to your computer and open iTunes

If you have ever connected your iPhone to your current computer before, this step should be largely automatic. In most cases, iTunes will automatically open whenever you physically connect your iPhone.

If you’ve never connected an iPhone to this computer, the process may take a little longer. Make sure you have access to a reliable, speedy Internet connection to make this process easier. iTunes is required for this particular trick, so yes, you will have to download it before you begin — a process Apple has made largely painless.

Step 2: Find the Info section for your iPhone

My iPhone InfoFirst, you should go to your Device menu. While the position of this menu tends to vary a little based on the device you are using and the version of iTunes you are working with, it’s usually in the top section of the iTunes menu, located next the drop-down menu you use for picking Music, Apps, Shows and other content. It looks like a tiny iPhone too, which helps when searching for it.

Once you have selected Device, you should enter a different sidebar menu that shows your iPhone above a list of the content stored on it. If you have multiple Apple devices connected to your computer, you’ll need to make sure that you select the right iPhone first. With the right menu activated, look all the way down at the bottom of the Device menu for an option that says “Info.” Select it.

Step 3: Choose to sync calendars

Sync with Outlook

In the Info section, look for Calendars (you can sync other information too, but from a work perspective Calendars is the most useful option). Under the Calendars heading you will find a fill-in option that says “Sync calendars from” with an option to select email clients. Make sure that you select Outlook so that iTunes knows where to pull/push data.

Step 4: Choose the right calendars and apply the changes

Sync Outlook Data

You will have an option to sync all calendars, or to choose specific calendars that you want to sync. A simple Outlook setup will probably only have one calendar to worry about, so you can safely choose “All calendars” without worrying. However, if you have multiple calendars or profiles on your Outlook setup, then you should probably check up on Selected calendars to see if there are any calendars you don’t want to sync.

Once you are sure syncing will affect only the calendars you want, choose Apply and wait for the first sync to take place. This one may take a few minutes, but before long the platforms will sort out their differences and you’ll have all the same calendar information on both devices. However, note that some calendar information may be less useful on your iPhone. Links to SharePoint, for example, may not work at your iPhone. We suggest running this sync past an administrator or IT expert in your company if you have any questions about how content will be affected.

Step 5: Get used to connecting your iPhone to your computer

Sync Outlook calendar with iPhone charging dock

Using cloud services to sync up is tricky when using two different providers with their own proprietary storage — there is some room to exchange Outlook information over iCloud for Windows, but that is heavily limited based on what cloud storage you use and what your company allows. That also means you will have to re-connect your iPhone to your computer every time you want to update your calendars. Syncing will happen automatically after this setup, but you will need the physical connection.

The simplest way to ensure consistent syncing is to set up an iPhone dock that’s always connected to your computer, and get in the habit of using it: This solution works best on professional desktops, but can become a little annoying on laptops. You can also (if allowed) switch to Wi-Fi syncing for your iPhone, although this may be hit-or-miss when it comes to reliability.

Note on issues: Did syncing mess your calendar up? Are you trying to retrieve lost data or fix an error that crept in when you were bouncing between platforms? It happens. But when you call up customer support, make sure you call Apple. Microsoft does not manage this syncing process at all, it is provided by Apple, and they are the ones you need to call if something goes serious wrong.


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