Fix & Reconfigure Mac Mail

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How to Fix & Reconfigure Mac Mail

We've all encountered problems with email at some point or another. You've got an account setup, but for some reason, it just never works quite right: doesn't receive, randomly won't send, warnings and popups.

There are a lot of pitfalls you need to watch out for when setting up an email account. If you have an account configured that isn't behaving, there are steps you can take to help make your emails work more reliably.


Accessing Mac Mail Settings

First, begin by going into the Mail menu, and going to Preferences. On the Preferences window, click the Accounts tab.

Step 1 - Configuring Outgoing Servers

Perhaps the most common culprit of confusion is the Outgoing Server settings. It is easy to look over the settings on the regular Accounts screen, but this only shows half of the story - that is, the settings for receiving email. Sending requires its own settings, which are, for the most part, entirely segregated into it's own section.

Under any of the accounts, on the General tab (as pictured above) click on the drop-down menu next to Outgoing Mail Server (SMTP). We often see a mess of servers here - so you might encounter something like this:


If you compare this to the list of email accounts on the Preferences > Accounts tab, it's possible you'll see a stark contrast - old accounts and addresses you removed, several showing Offline, and often a different amount to those listed on the normal Accounts screen.

To clean this up, click on the Edit SMTP Server List... button. This will bring up a screen where all of the Outgoing settings live.

First, find and click on the most relevant server in the list. If there isn't one, you can always add one using the + button.

Then, simply complete the fields as follows:

Description The email address
Server Name Your Outgoing Server, eg,
TLS Certificate None (Just leave this one alone)

Next, click on the Advanced tab.

This part is very important. While it may not require you to type in a username or password, it is often mandated by the server - else Mail won't send.

Fill out the details as follows:

Automatically Detect and Maintain Account Settings Unchecked
Port 587
Use SSL Optional - See Notes
Authentication Password
Allow Insecure Authentication Off
User Name Your email address
Password Your password

Step 2 - Configuring Incoming Servers

When you're done, click OK. Now we will focus on the "main" account settings screen. Begin by clicking the Advanced tab.

The default options should be fine, and some are of personal preference anyway. But you may want to revise these specific ones:

Automatically detect and maintain account settings Unchecked
IMAP Path Prefix INBOX
Port (IMAP)

143 (Non-SSL)
993 (SSL)
Port (POP)

110 (Non-SSL)
995 (SSL)
Use SSL Optional
Authentication Password

Note that you should never need to actually change the server port. However, Mac Mail sometimes will automatically set Port 143 with SSL on, which is incorrect. You will find simply toggling the Use SSL checkbox on or off will change the port number for you to the correct number.

Next, click on the Account Information tab.

Ensure the fields are completed as follows:

Description Your Email address
Email Address Your Email address
Full Name

The name of yourself, your department or your business - whatever you want people to see in their inbox
Incoming Mail Server

Your Incoming Server, eg,
Username Your email address
Password Your password
Outgoing Mail Server (SMTP)

Select the server configured earlier, which should be identified by your email address

When done, click on another account or close the window to save the changes.


Step 3 - Housekeeping

It is best to go through and revise the settings for all of your accounts in this way. Ideally, you want to create pairs of accounts - that is, for every incoming server, you have a single outgoing server, removing any unnecessary accounts or servers along the way.


Step 4 - Connection Doctor

The Connection Doctor is a utility within Mac Mail which tests every account (even inactive ones) to verify if the details for that account are complete and functional. It can help pinpoint which accounts you may need to focus on when checking the settings as described above.

It can be a little intimidating to look at, but it's quite useful when broken down. The best thing to do is to be patient with it, and yourself - give it time to complete its test, and yourself time to read through the results. If you are experiencing issues, glancing at it will only tell you what you already know - take the time to read the errors presented to better understand why there is a problem.

To open the Connection Doctor, click on the Window menu, and click Connection Doctor.


The Connection Doctor will open and begin checking all of the accounts. Ensure your internet connection is working well before attempting to use the Connection Doctor, to avoid any false negatives.

When testing, be sure to scroll through the list to view all of the configured servers. Do be patient as it may take a short time to complete testing each account, especially if you have many. As you would expect, Green indicates everything is well for a given server, and Red indicates a problem.

Generally speaking, an error with an IMAP or POP server means you need to check the Incoming settings. An error with an SMTP server means you need to check the Outgoing settings. Locate the account with the listed description in the relevant area, and check the settings.

The Connection Doctor will also give hints as to the fault, such as an incorrect username or password. Connection issues may indicate an incorrect port, incorrect SSL settings, or suggest that your public IP address may be blocked at the server.

In this example above, I can see that everything works well except for one SMTP (Outgoing) server. The error indicates a username or password issue, however I know the username and password for the same account (for the Incoming server) is OK, so I would refer to the Step 1 instructions above to locate the username and password settings for this account and re-enter them.

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