Alias setup in Outlook 2016 / Office365

Introduction

Outlook has never handled aliases very well, typically requiring a complicated setup procedure.

As messages sent to aliases are forwarded to one or more real mailboxes, they do not have their own incoming server settings. So, we've created a fake POP3 service to avoid having to configure complex send/receive settings.

One does however need to be able to send using the alias address in your message's from field, so you will use your primary mailbox settings for outgoing email.

Configuration

Add a new POP3 account

The POP3 settings will be "fake"
The SMTP settings will use the real mailbox's credentials.

When following the below instructions, be sure to replace user@domain.name with the real mailbox's address and alias@domain.name with the alias' address.

POP3 Settings

Open Outlook
Click File, then click Account Settings, and finally Account Settings.
On the E-mail tab, click New.
Click Manually configure server settings or additional server types, and then click Next
Click Internet E-mail, and then click Next

Your name: The name you wish recipients to see
E-mail Address: alias@domain.name
Account Type: POP3
Incoming mail server: mail.zootzone.com
Port number: 10123
Outgoing mail server (SMTP): smtp.zootzone.com
SSL: Off (do not select)
User name: fakepop
Password: fakepop

SMTP Settings

Click More Settings.
Click the Outgoing Server tab
Select the My outgoing server (SMTP) requires authentication check box.

Enter your mailbox's authentication credentials.

User name: user@domain.name
Password: password for user@domain.name

Click the Advanced tab
Select the This server requires an encrypted connection (SSL) check box.

Either (preferred):

Outgoing server (SMTP): 465
Use the following type of encrypted connection: SSL

Or (if the above does not work for you):

Outgoing server (SMTP): 587
Use the following type of encrypted connection: StartTLS or TLS

Click OK.
Click Next

The account settings that you entered are tested.

Click Close.
Click Finish.

From Field Settings

You may have to enable the From field in Outlook, in order to send messages which appear to originate from the alias:

To do this, follow these steps:

Click New E-mail to open a new email message.
Click the Options tab.
Access the Show Fields group
Click From to enable the From field in all new email messages.