How To Set Up Email in Outlook 2016 for Mac

Pre-Flight Check

Step #1: Add or Edit the Email Account

  1. To set up a new email account or edit the settings on an existing one, click the Tools menu and then select Accounts to open the Accounts panel.

    Outlook2016MacToolsAccounts

  2. The setup process is slightly different depending on whether you have any existing email accounts configured in Outlook 2016:
    • Setting up your first email account: If this is your first time setting up Outlook 2016, you will need to click on the envelope icon next to the third option: Other Email (iCloud, Google, Yahoo!, or other accounts):

      Outlook2016MacAccountsPanel1

    • Setting up an additional email account: Once any email account has been set up in Outlook 2016, additional accounts can be added by clicking the plus sign in the lower left corner and selecting Other Email… from the pull-down menu:

      Outlook2016MacAddExtAcct

    • Changing the settings for an existing email account: Click on the account’s name in the account list on the left to make changes to any existing account in Outlook 2016, and skip ahead to Step #4: Editing an Existing Email Account.
      Note: You cannot edit an existing email account to directly change its connection method. To change an account from POP to IMAP or vice versa, simply add a new account for the email address as described below and select the desired connection type. Outlook 2016 will allow you to have multiple accounts for the same email address, so an account for sample@example.com using IMAP can coexist with an account for sample@example.com using POP. To prevent data loss, do not delete the existing account before adding a new one.

Step #2: Configuring a New Email Account

On the account information panel, enter the information as follows:

Outlook2016MacAcctInfo

At first, you will only see the E-mail address and Password fields. Once you enter your email address, Outlook 2016 will recognize that you’re not attempting to connect to a web service such as iCloud, Google, or Yahoo, and will automatically expand the window to reveal all the fields shown in the image above.
  • E-mail address: requires your complete email address, such as sample@example.com.
  • Password: is the password associated with the email account.
  • User Name: is your full email address. It should exactly match what you entered into the E-mail address field above.
  • Type: you may select IMAP or POP. IMAP is recommended for its ability to sync messages between multiple devices (to learn more about the difference between the protocols, see IMAP vs POP3 email).
  • Incoming server:
    • When using standard (non-SSL) settings, use mail.yourdomainname.com
    • When using secure (SSL) settings, use the server’s hostname (host.yourdomainname.com)
    • The default port numbers should not need to be changed unless you have configured your server to use non-standard ports (not common)
    • Check the box next to Use SSL to connect (recommended)
  • Outgoing server:
    • When using standard (non-SSL) settings, use mail.yourdomainname.com
    • When using secure (SSL) settings, use the server’s hostname (host.yourdomainname.com)
    • The default port numbers should not need to be changed unless you have configured your server to use non-standard ports (not common)
    • Check the box next to Use SSL to connect (recommended)

Once you’ve entered all the requested information, click the Add Account button at the bottom of the window to create the account with your specified settings.

Step #3: Configure Security Settings

When you add your email account, an alert window may prompt you to review security settings. This is expected if you have not already purchased and installed a signed, third-party verified SSL certificate on your mail server. If you see no such prompt, then you’re all set and can begin using Outlook 2016 with your email account immediately.

If you do get a security prompt, which specifies that information that you view and send will be encrypted, note that Outlook 2016 will not be able to verify the security of the certificate through a third-party because you are the only authority validating it:

Outlook2016MacSSLAlert

If you wish to proceed with the connection, you have two options:

  • You can click the Continue button to proceed, with the caveat that you may need to accept the warning each time Outlook connects.
  • Or, you can permanently store the certificate and treat it as trusted, by clicking Show Certificate and then checking the box next to Always trust … before clicking Continue. You will need to authenticate with your password to store the exception for your self-signed certificate.

Outlook2016MacSSLAdd

Note: A self-signed certificate uses the same level of encryption as a third-party verified certificate; the difference is that it is you who are verifying your server’s identity and not a third party who is paid for the service. However, if you would prefer to use a third-party verified SSL certificate to cover core services (cPanel/WHM, POP3, IMAP, SMTP and FTP) on your server, you can find instructions for ordering and installing an SSL certificate at Install an SSL Certificate on a Domain using cPanel, and you’ll find a guide to installing your certificate on email and other core server services at Installing Service SSLs in cPanel. Should you find that you need any assistance, please feel free to contact a Heroic Support® technician who can assist with obtaining and installing an SSL from the vendor of your choice.

Once connected, Outlook 2016 will download your mail from the server along with any custom directories you’ve added, which will be synced by default.

Step #4: Editing an Existing Email Account

To change the settings on an existing email account, click the Tools menu and then select Accounts to open the Accounts panel.

Click on the name of the account in the left pane, and make the desired changes:

Outlook2016EditAcctExtOpt

  • User Name: is your full email address. It should exactly match the value of the E-mail address field above.
  • Password: is the password associated with the email account.
  • Incoming server:
    • When using standard (non-SSL) settings, use mail.yourdomainname.com
    • When using secure (SSL) settings, use the server’s hostname (host.yourdomainname.com)
    • The default port numbers should not need to be changed unless you have configured your server to use non-standard ports. If you do need to configure mail on a different port, you can check the box next to Override default port and enter the appropriate incoming mail server value (POP3 should be 110 for non-SSL connections and 995 when using SSL; IMAP should be 143 for non-SSL connections and 943 when using SSL.)
    • Check the box next to Use SSL to connect (recommended) for a secure connection.
  • Outgoing server:
    • When using standard (non-SSL) settings, use mail.yourdomainname.com
    • When using secure (SSL) settings, use the server’s hostname (host.yourdomainname.com)
    • The default port numbers should not need to be changed unless you have configured your server to use non-standard ports. If you do need to configure mail on a different port, you can check the box next to Override default port and enter the appropriate outgoing mail server value (25 for non-SSL connections and 465 when using SSL; Unlike many other mail clients, Outlook 2016 does not require you to use port 587 on Mac OS X).
    • Check the box next to Use SSL to connect (recommended) for a secure connection.
    • The More Options… button will allow you to configure authentication for the outgoing (SMTP) mail server:

      Outlook2016MacEdAcExMOpt

      • Authentication: Typically, Use Incoming Server Info is sufficient, but if you receive connection errors due to SMTP authentication, you may need to select User Name and Password. Do not select None; you will not be able to send mail if None is selected as the authentication type.
      • User Name: This field can only be filled in if you use the User Name and Password authentication type. If enabled, it must be the full email address.
      • Password: This field can only be filled in if you use the User Name and Password authentication type. If enabled, use the email account’s password.

Bonus: Select IMAP Folders to Sync

By default, Outlook 2016 for Mac OS X will sync all IMAP folders. To specify which ones you want to sync, pull down under the Tools menu and select IMAP Folders… to bring up the Folder Browser.

Outlook2016MacIMAP

In the Folder Browser, you will see a list of your accounts in the left pane.

  • In the first pane, click on the IMAP account’s name
  • In the second pane, click on INBOX (or the desired custom folder, if listed)
  • In the third pane, click on the folder to which you want to subscribe or unsubscribe.
  • Folders to which you already are subscribed will be displayed in bold type, while folders to which you are not currently subscribed will be displayed in a light-face font. Note that on some versions of Mac OS X, the distinction can be almost imperceptible.
  • Clicking on the name of a folder to which you are subscribed will allow you to click the red ( – ) Unsubscribe button in the top-left menu, and clicking on the name of a folder to which you are not subscribed will allow you to click on the green ( + ) Subscribe button in the top-left menu.
  • You can not unsubscribe to default account folders, such as Drafts, Junk, Sent, and Trash.

Outlook2016MacFldOpt

 
 

How To Set up a New Email Account in OS X 10.11

How To Set up Email in OS X 10.11
I. How To Set up a New Email Account in OS X 10.11
II. How To Modify an Existing Email Account in OS X 10.11

Pre-Flight Check

Step #1: Create the Account

  1. Launch Mail by clicking on its icon in the dock. Under the Mail menu, select Add Account.
  2. On the Choose a Mail account provider screen, select the radio button next to Other Mail Account and click the Continue button.
    OSX 10.11 Add Account Screen
  3. On the Add a Mail Account screen, enter your name, the email address and the email account’s password.
    OSX 10.11 Add New Mail Account Screen

Step #2: Account Settings

  1. At this point, you should see an additional popup window with a place for you to add additional settings.
  2. You will need to ensure that all the fields are completed:OSX 10.11 Additional settings
    • Email Address is the full email address you’re setting up.
    • User Name also is the full email address.
    • Password is the email account’s password.
    • Account Type will be IMAP or POP, depending on your preference. For its ability to keep email in sync across multiple devices (desktop, laptop, phones and tablets), IMAP generally is recommended.
    • Incoming and Outgoing Mail Server
      • If you are using non-SSL settings, both the Incoming Mail Server and Outgoing Mail Server will be your domain name: mail.yourdomainname.com (or simply yourdomainname.com).
      • If you are using SSL settings, both the Incoming Mail Server and Outgoing Mail Server will need to be set to the server’s hostname (e.g., host.yourdomainname.com).

Step #3: Security Settings

  1. If you set up the email account with standard connection settings (mail.yourdomainname.com), or you set up the account with secure SSL settings and have an SSL certificate installed on your mailserver, you can skip this section and proceed to Step 4. However, if you’re using SSL settings (host.yourdomainname.com) and your server has a self-signed (free) SSL certificate installed on the mail server, you should see a popup notification about the server certificate:
    OSX 10.11 Self-signed SSL Certificate Notice
  2. If you receive this notification, you will need to click either the Continue button to accept the certificate and proceed, or the Show Certificate button to inspect it. Should you wish to permanently store the certificate and add it to the Keychain, you can check the Always trust box before selecting Continue. Depending on your security settings, choosing to permanently store the certificate could require you to enter your password to add it to the Keychain.
    OSX 10.11 Can't Verify Self-signed SSL Certificate
  3. Note: A self-signed certificate uses the same level of encryption as a verified certificate, except that it is you who are verifying your server’s identity, rather than a third party. However, if you would prefer to use a third-party verified SSL certificate to cover core services (cPanel/WHM, POP3, IMAP, SMTP and FTP) on your server, you can find instructions for ordering and installing an SSL certificate at Install an SSL certificate on a Domain using cPanel, and you’ll find a guide to installing your certificate on email and other core server services at Installing Service SSLs in cPanel. Should you find that you need any assistance, please feel free to contact a Heroic Support® technician who can assist with obtaining and installing an SSL from the vendor of your choice.

Step #4: Finishing Up

  1. Ensure that the box next to Mail is checked and then click on Done to complete the setup.
  2. You’re now ready to begin using your email account with Mail.

 

How To Modify an Existing Email Account in OS X 10.11

How To Set up Email in OS X 10.11
I. How To Set up a New Email Account in OS X 10.11
II. How To Modify an Existing Email Account in OS X 10.11

Pre-Flight Check

You can edit an email account that already has been configured in Mail, for example should you decide to switch between non-SSL and SSL settings or update the password.

Note: You cannot edit an existing email account to switch its account type from POP3 to IMAP or vice versa. To change the account type, you must add a new email account of the desired type (POP3 or IMAP). Adding a new account with a different connection type should not require you to delete the old one in most mail clients.

To avoid data loss, please use caution any time you change an email account’s connection type or delete an email account. Removing an email account from a mail client also will remove all messages associated with it on the device and, specifically in the case of POP accounts that are not configured to retain mail on the server, there may be no way to recover those messages. If you have any doubt or questions, please contact Heroic Support® for guidance.

Since any changes must be made on both the incoming and outgoing servers, updating the email account’s password or switching between non-SSL and SSL settings is not as simple as toggling a single setting, but the steps are easy to follow.

Step #1: Configure Incoming Server Settings

  1. You set the incoming mail server in the Internet Accounts preferences pane. To access it, select Accounts from the Mail menu.
  2. On the Internet Accounts preferences panel, select the name of your email account from the left pane to update the password or change the incoming server name or connection type.OSX 10.11 Incoming Mailserver
  3. Update the Password
    • To update the email account password, enter the new password into the Password field in the Internet Accounts preferences pane.
  4. Change the Incoming Server Name or Connection Type (SSL/non-SSL)
    • Click the Advanced button at the bottom right of the Internet Accounts preferences pane to edit the Hostname via a popup panel.
      • SSL settings will use the server’s hostname (e.g., host.yourdomainname.com)
      • Standard non-SSL settings will use the domain name (yourdomainname.com or mail.yourdomainname.com).
    • Once you have changed the Hostname, click OK.

Step #2: Configure Outgoing Server Settings

  1. Select Preferences from the Mail menu to open the Internet Accounts preferences pane, then click on the account in the left menu.
  2. On the Account Information tab, locate the Outgoing Mail Server (SMTP) row and select Edit SMTP Server List from the select menu.
    OSX 10.11 Outgoing Mailserver
  3. Change the Outgoing Server Name or Connection Type (SSL/non-SSL)
    OSX 10.11 Account Information

    • Click on your mail server’s name in the top pane to select it, then change the Server Name on the Account Information tab to the desired value.
      • SSL settings will use the server’s hostname (e.g., host.yourdomainname.com)
      • Standard non-SSL settings will use the domain name (yourdomainname.com or mail.yourdomainname.com).
    • Once you’ve changed Server Name to reflect the desired connection type, click on the Advanced tab to configure SSL settings.
      OSX 10.11 Advanced Account Settings

      • Port: This should remain 587 regardless of connection method.
      • Use SSL: If you are using secure (SSL) settings, ensure that the Use SSL box is checked. If you are using standard, non-SSL settings, Use SSL should be unchecked.
      • Authentication should be set to Password regardless of connection method.
      • Both the User Name (full email address) and Password fields should be filled out. You can update the email account password by entering the current password into the Password field.
  4. Your email account will start using the new settings as soon as you click the OK button.

 

How To View Full E-Mail Headers

Full email message headers provide invaluable information when trying to track down a problem. Just a few of the items included in the headers are:

  • The server from which an incoming email originated
  • The actual address from which the message was sent
  • The message’s intended recipient
  • Whether the message was accepted or rejected by the recipient’s mail server
  • If the recipient’s mail server rejected the message, the reason for that rejection
  • Any messages returned by the mail server

This guide will show you how to view full headers in several popular email clients and web services. Once the full headers are in view, you can copy and paste them for your own reference or to include them when contacting Heroic Support®.

Mozilla Thunderbird

  • Open the message in its own window by double clicking on it in the list of messages.
  • In the menu bar, select View, then Headers, and click All.
  • Alternatively, you may be able to click on View followed by Message Source.

Mac OS X Mail

  • Open the message in its own window by double clicking on it in the list of messages.
  • In the menu bar, click on View, then Message, then All Headers (or Raw Source on older versions of Mail).

Outlook 2016, 2013, and 2010

  • Open the message in its own window by double clicking on it in the list of messages.
  • Click on the File tab.
  • In the File window, click Properties.
  • The Internet headers section contains the full email headers.

Windows Mail/Windows Live Mail

  • In the list of messages, right-click on the message in question and choose Properties.
  • In the Properties window, click on the Details tab.
  • The headers will be displayed in the section labeled Internet headers for this message.

Outlook.com Web Interface

  • Right-click on the message while viewing it in your inbox.
  • On the menu that appears, click on View Source.

Gmail Web Interface

  • Open the message by clicking on it in the list of messages.
  • Click on the More icon (the small downward-facing arrow next to the Reply button at the top right of the message).
  • On the menu that appears, click on Show original.

Yahoo Mail Web Interface

  • Open the message in question by clicking on it in the list of messages.
  • Under the More menu above the message, click on the link marked View Full Header.

Horde Webmail

  • Open the message by clicking on it in the list of messages.
  • Click on the link marked Show All Headers or, on newer versions of Horde, select View Source under Other Options in the preview pane. View Source also is available at the top-right of the full message view.

RoundCube Webmail

  • Open the message by double-clicking on it in the list of messages.
  • Click on the link marked Message Source. Newer versions of RoundCube have a downward-facing arrow that displays Toggle raw message headers when you move your mouse over it. The icon is at the bottom of the message header section, to the far right of the date field.

SquirrelMail Webmail

  • Open the message by clicking on it in the list of messages.
  • Click on the link marked View Full Header in the Options section at the top of the message.

 
 

IMAP vs POP3 E-Mail

If you contact support regarding an e-mail problem one of the questions we will ask you is how you are accessing your e-mail. If you are using a client such as Outlook, Outlook Express, Thunderbird, Mac OS X Mail, or any other modern e-mail application we will ask if you are using POP3 or IMAP for your incoming e-mail.

There are pros and cons to both methods, but with some careful consideration of what is most important to the user(s) you can make a (well) informed decision.

Continue reading “IMAP vs POP3 E-Mail”

Configuring an Alternate Port for Outgoing Mail Traffic

Many large ISPs restrict the access to port 25 on their networks to attempt to stem the tide of spam sent out from compromised computers.  If your ISP is restricting access to port 25 you will not be able to send e-mail through your server, but by enabling SMTP (Simple Mail Transfer Protocol) on a different port, like 26, it may be possible to circumvent the restriction.
Continue reading “Configuring an Alternate Port for Outgoing Mail Traffic”