A tutorial for Outlook 2010, Outlook 2013, and Outlook 2016 is at "Tutorial: Set up Outlook.com account to sync Calendar and Contacts"
All outlook.com accounts are running on Office 365 servers and all Outlook.com accounts set up in Outlook desktop need to be configured as an Exchange account. Instructions are below.
This works with Outlook 2010 and above with Outlook.com Exchange accounts to sync your calendar and contacts with other computers or smartphones "over the air" when your personal email account is POP3 or IMAP. (Outlook 2007 will sync Outlook.com and Office 365 Exchange accounts until October 31, 2017; after that date, Outlook 2007 users will suffer from degraded service. If upgrading to a newer version of Outlook is not an option, use Windows 10 Mail, or switch to POP3 or IMAP for email-only.)
All you need is a Microsoft Account. If you have a Microsoft account for your personal address, you will need to add an "Outlook.com alias" to the account before you can add it to Outlook. If the alias is not set as the default address for the account, it will be added to Outlook using an Outlook_big-long-code@ format for the address). Set the outlook.com address as Primary to fix this.
Using an Outlook.com account for email? See Configuring an Outlook.com account in Outlook.
You do not need to configure Outlook.com to pull in your other email accounts to use it for Calendar and Contacts. In fact, I do not recommend adding your email account as a connected account to outlook.com - use outlook.com only for calendar and contacts.
You'll need to move or copy existing appointments and contacts to the new Outlook.com data file. You can move the appointments and contacts between folders within Outlook using drag and drop or the Move to command.
You can set the Outlook.com Microsoft Account as your default data file (this puts the calendar on the To-Do Bar) but I do not recommend setting it as the default email account.
If you enabled two-factor authentication on the Outlook.com account, you'll need to generate an app password to use with the account in Outlook. Log into Outlook.com and check your account options for instructions.
Setup Account using New Outlook.com Server
Create a "Microsoft Account" for your email address and use that in Outlook. If you are using a non-Microsoft domain (like Comcast.com, gmail.com, or your own domain name), you'll need to add an outlook.com alias to your Outlook.com account before you can set it up in Outlook.
When the Outlook.com account is hosted on the new Outlook.com servers, it can be added to Outlook as an Exchange account but you'll need to use auto-account setup to set it up.
Set up the Microsoft Account in Outlook
These are the basic steps to configure Outlook for usability.
Create a "Microsoft Account". Set up the account in Outlook using the steps in the next section. You need to use auto account setup to set up accounts now that Outlook.com is hosted on Office 365 Exchange server and will need to use an Outlook.com address to sign in.
You'll have two accounts in Outlook: your ISP or "real" email and the Outlook.com account.
Outlook 2003 and 2007 will use the default email account for New messages; Outlook 2010, 2013, and 2016 will use the account associated with the folders you are looking in. This means if you are viewing the calendar in Outlook.com data file and start a new message, Outlook will use the Outlook.com account to send the message. However, you can edit the registry to mimic the older behavior from Outlook 2007 so you always use default email account as set in File, Account Settings. See registry edit for default accounts for details (includes a ready-to-use reg file). I recommend setting this registry value.
This option was added to Outlook 2016's Mail settings. In File, Options, Mail, look in the Send messages section about two-thirds down for Always use the default account when composing new messages.
Set the Outlook.com account to be the default data file on the Data Files tab. This puts the calendar in the To-Do bar and new appointments and contacts will go into it's Calendar and Contacts folder.
The final piece of the puzzle: in File, Options, Advanced, you can set your "real" Inbox to be the default start up folder.
If you want, you can rename the Microsoft account.
After you set up the account in Outlook, move your appointments and contacts to the Outlook.com data file folders. Hint: it's easier if you use a List view. Select all, drag and drop.
If you want to remove the calendar and contacts folder from the .pst your "real" account uses, see Delete Special folders. If you are using an IMAP account in Outlook 2013 or newer, close Outlook and delete the IMAP account's data file. When Outlook restarts, it will create a new data file without the special folders. Don't forget to move the appointments, contacts, and tasks to the Outlook.com folders first.
Configure outlook.com account for syncing
In this tutorial, I'm adding a Microsoft Account that uses the same email address as a POP3 account in the Outlook profile and setting it as the default data file, so the Calendar and Contacts folders are the default folders.
The process is the same for IMAP accounts.
Outlook 2013 and 2016 Exchange ActiveSync Configuration
Exchange Active Sync (EAS) was turned off for Outlook desktop clients in February 2017. (Smartphones can still use it.) Anyone using EAS will need to remove the account from Outlook and add it back using Auto account setup.
Using the Outlook Connector with Outlook 2010 / older
With the move to the new server, the Outlook Connector no longer works.
Registry key for Outlook 2010 SP1 and above
Out of the box, Outlook 2010 SP1, Outlook 2013, and Outlook 2016 use the default account for Send to commands but not for new messages created while viewing a data file that is used for delivery. This means if you send a message while viewing the outlook.com calendar, it will be sent via the Outlook.com account. This is not necessarily the desired behavior when you are using an Outlook.com account only for syncing calendar and contacts.
Outlook 2016 users can make this change in File, Options, Mail. Look in the Send messages section about two-thirds down for Always use the default account when composing new messages.
For Outlook 2010 and Outlook 2013, you'll need to set a registry value to always force the use of the default account.
To force all new messages to use the default email account, regardless of which data file you are viewing, browse to the following registry subkey in Outlook and add a DWORD named NewItemsUseDefaultSendingAccount:
DWORD value: NewItemsUseDefaultSendingAccount
DWORD value: NewItemsUseDefaultSendingAccount
DWORD value: NewItemsUseDefaultSendingAccount
The registry key above changes the account on all new messages to the default email account but does not apply to meeting requests. For this we need to use a macro. This goes in ThisOutlookSession.
See How to use VBA Editor for instructions.
Private WithEvents m_Inspectors As Outlook.Inspectors Private WithEvents m_Inspector As Outlook.Inspector Private Sub Application_Startup() Set m_Inspectors = Application.Inspectors End Sub Private Sub m_Inspectors_NewInspector(ByVal Inspector As Outlook.Inspector) Set m_Inspector = Inspector End Sub Private Sub m_Inspector_Activate() Dim olNS As Outlook.NameSpace Set olNS = Application.GetNamespace("MAPI") If TypeName(m_Inspector.CurrentItem) <> "AppointmentItem" Then Exit Sub End If ' so it doesn't fire when you open a meeting If m_Inspector.CurrentItem.CreationTime < Now() Then Exit Sub End If ' (1) this the default account If m_Inspector.CurrentItem.SendUsingAccount <> olNS.Accounts.Item(1) Then Set m_Inspector.CurrentItem.SendUsingAccount = olNS.Accounts.Item(1) m_Inspector.currentItem.Display End If Set m_Inspector = Nothing Set olNS = Nothing End Sub
Add your email account to Hotmail or Outlook.com
I DO NOT recommend using this method at this time. Outlook.com is using an ugly address (email@example.com, or as I call it, outlook_ugly@) as the From address, not the "Microsoft Account" address. Keep both accounts in your profile and use the registry key above to force Outlook to use the default account as the default for all email.
If you use a Microsoft Account from another domain and want to bring your email into Hotmail or Outlook.com, log onto your account online (in Internet Explorer), go to the gear icon (next to your name) > More mail settings > Sending/receiving email from other accounts and add your POP3 account username and password. This tells outlook.com to go out and get the email from that account.
If you do this, you can read your email online, at outlook.com as well as in Outlook. You should remove the POP3 account from your profile, otherwise you will have duplicate messages in Outlook.
If you send mail through the Hotmail servers, some antispam filters may reject email from the account because the address is not a Microsoft domain but using Microsoft SMTP servers. (Yahoo Groups rejects messages sent using this method.) If you control your own DNS you should add an SPF record for hotmail. The SPF record you need is v=spf1 include:hotmail.com ~all