If the iCloud addin gets disabled every time you restart Outlook, see 'iCloud Doesn't Sync' for the registry key to force it to always load. The following shows how you can quickly add Outlook calendar to iPhone. Note: If you aren’t using upgraded reminders, you can also see your iCloud Reminders (called Tasks) in Outlook. Click on Add file/ Add Folder button to add your OLM file. Download and install the desktop version if you do not have it yet - get the software from the official website. The list of folders on Outlook are old ones which have been deleted on iCloud. OneCalendar integrates all your calendars into an easy-to-read overview. Now, head to the official website of the mail client or use the Outlook app.