How to sync Outlook desktop calendar to Outlook.live.com calendar

Hi Karl,

Thanks so much for the response. Following your guidance, I was able to successfully sync my Outlook desktop and Outlook live calendars (the latter of which includes syncing with the iPhone Outlook app, so all 3 calendars now sync together). Thanks so much for your help!

In case it helps anyone in the future, the following are the specific steps I took (Windows 11):

1. Open Outlook.live.com (not Outlook desktop)
   1. Click on the settings wheel icon in top-right corner
   2. At the bottom of the side ribbon that appears, click View all Outlook settings
   3. In the Settings window that appears, click Mail on the lefthand side
   4. Then click Sync email in the options just to the right of the settings options where you clicked Mail.
   5. Then click Manage or choose primary alias under Email aliases
   6. This takes you to the webpage: Manage how you sign in to Microsoft
   7. If you already have an @outlook.com email account associated with your Microsoft account, choose that account as the primary alias for your Microsoft account (click Make primary)
   8. If you don’t already have an @outlook.com email account associated with your Microsoft account, you can create one by clicking on Add email, which takes you to the Add an alias webpage where you can create one with the option Create a new email address and add it as an alias. Once you’ve created an @outlook.com email account, go back to the Manage how you sign in to Microsoft page and make the @outlook.com email account your primary alias (see g. above). NOTE: Your new @outlook.com email account uses the same password as your Microsoft account
   9. Finally, to make sure Outlook.live.com is using your new @outlook.com email account as the primary alias through which to sync across devices, log out of Outlook.live.com then sign back in using your new @outlook.com email account primary alias (again, the password is still your same Microsoft account password).
2. Open Outlook desktop
   1. Click on the Calendar icon in the bottom-left corner. (Or open the Calendar desktop app directly without opening Outlook desktop)
   2. Once Calendar desktop opens, click on the settings wheel icon in the very bottom-left corner
   3. In the Settings ribbon that appears on the left, click Manage Accounts, the click + Add account
   4. Add your @outlook.com email account and sign in with that account (again, the password is your Microsoft account password)
3. Wait a few ticks for the Outlook.live.com and Outlook desktop accounts to sync
   1. If there is a long delay, close and reopen your Outlook desktop calendar and log off then back on to your Outlook.live.com account (using your @outlook.com email account primary alias).
   2. All new calendar events added to the Outlook.live.com account calendar and Outlook desktop calendar will now show up in the other calendar (after a short sync delay)
   3. However, although it appears that calendar events previously added to your Outlook.live.com calendar will now appear on your Outlook desktop calendar, calendar events previously added to your Outlook desktop calendar do not appear on your Outlook.live.com calendar (only new ones moving forward). To resolve this, I believe you’d have to download your Outlook desktop calendar and manually add it to your Outlook.live.com account calendar. But everything moving forward (i.e., all new events) will sync across all Outlook calendars using your @outlook.com email account alias.

Hello Seth

Hi, I'm Karl and will be happy to help you today.

Just co cover off a few things from your description.

#1 - To share contact /calendar data across multiple devices requires that this information is stored in an Exchange based account (which includes Outlook.com and all devices need to connect to this account

#2 - In order to add the Outlook.com account associated with your Microsoft Account, you need to add a <NEW> Outlook.com alias email address to the account and make it the <Primary Alias>. When that is done, the Outlook.com needs to be added to Outlook desktop using the new Outlook.com primary alias address

#3 - Contact /calendar data is not natively sync'd with the server using Outlook desktop for any POP or IMAP account (including @Gmail) so it cannot be shared across devices without the use of a 3rd party sync tool

The above applies to any version of Outlook desktop