Troubleshooting Apple Mail and Outlook can be a pain in the butt but we post some helpful content to make it less painful.  We will walk you through some key topics such as IMAP.  IMAP rules the world.  Most people use it for accessing their email and syncing it among all devices.  IMAP is an email protocol that’s better than POP but not as feature rich as Exchange Active Sync.   With that said, we will display how bizarre and frustrating it can be work with these protocols if you do not have the right mail configuration information to set it up.  Sometimes, it’s as easy as automatic config where you enter the email and password in the email client; and you are good to go.  The complications usually reside with residential ISPs providing their own email hosting that user’s utilize and attempt to configure on their Mac or PC email client.  For these less fortunate, read below.

Copy and Paste Password

Use a notepad to type out the password and maybe some other  pertinent information.  Then you can paste the password first into webmail.  Once successful login there, use it for pasting the password into the email client setup.  I don’t know how many times I’ve fouled up setup through fat fingering a password.  Please remember this tip and save those email settings once you figure them out for later.

What are my email settings?

In this scenario, we are setting up a Time Warner residential email.



Additional Support



Why Multiple Email Configuration Resources?

This is a very tricky email setup.  Some email settings work well from the TWC website.  Others, you may have to defer to a third party like Microsoft support for a successful setup.  In out case,  the first link worked best for the Mac.  The second link worked best for Windows.   However, they vary from app to app in Mac as explained below.


TLS and SSL tend be pretty interchangable on the Mac.  Not so much on Windows

Also, simply download and subscribe to Office 2016 and use the support link above if you give up and need a third party hand.  The site below is very good resource in general for email.

Notepad –  Scratch Notes

Incoming Mail:  143 none
Sending: 587 TLS  (SSL sometimes works just as well)
*use password  as the authentication method
Full email address:

Apple Mail – Accounts

Below is the main menu for email account setup and a proven successful setup for Apple Mail.

Troubleshooting Apple Mail and Outlook











Apple Mail – SMTP

SMTP delivery settings for sending Apple Mail.

Troubleshooting Apple Mail and Outlook

Apple Mail – Incoming Mail Settings

Troubleshooting Apple Mail and Outlook usually comes down to sending… incoming mail server or sending… SMTP server.  Setting for incoming mail works port 993 and SSL enabled.  This will not be a successful setting on Outlook and is completely different on Outlook for Mac.  Outlook for Mac uses the default SSL port.

Apple Mail – Doctor Diagnose

The little hazard symbol features a doctor diagnoses feature that comes in handy when troubleshooting.


Apple Mail – Import Mailboxes

Many people can’t store all their email on the email server hosting provider.  There are numerous reasons behind this.  The mail server may have limited space or you simply have too much email for IMAP to function properly.  Whatever the case, you need to import mailboxes if you ever lose those messages all the local drive of the computer.

Troubleshooting Apple Mail and Outlook

Apple Mail – Backup and Recovery


Knowing where the mail database is key to a successful disaster recovery plan.  Viewing the date modified will give you clue of how recent or stale the mailbox is.  This is important in disaster recovery.  Pay attention to the path of where the mail was stored on the computer.   You need to restore it to the same location.


Troubleshooting Apple Mail and Outlook







Apple Mail – Import location

Once the recovery data is downloaded, unzip it, and restore it or copy it back to the proper location.  Then import inbox.mbox and it will appear below in the Apple Mail client interface.

Troubleshooting Apple Mail and OutlookApple Mail Imported mail is burried below in the left mail.

Troubleshooting Apple Mail and Outlook





Outlook 2016 for Mac – Accounts

Displayed below is a proven setup on Outlook 2016 for Mac

Incoming Mail: 143 (SSL enabled)

Troubleshooting Apple Mail and Outlook

Outlook 2016 for Mac – SMTP (More Options)

Authenticate with the incoming mail server.


Troubleshooting Apple Mail and Outlook






Outlook 2016 for Mac – Advanced

Sometimes the IMAP Root Folder:  need “inbox” added.  Not in this case.

Troubleshooting Apple Mail and OutlookOutlook 2016 for Mac – Advanced – Security

The defaults are pretty much always fine here.


Troubleshooting Apple Mail and Outlook






Outlook 2011 for Mac – Accounts.

The settings are very similar to Outlook 2016 for Mac.  However, I could not get 2011 to send.  I will work on this at some future point.  We simply upgraded to Outlook 2016 and the email address automatically configured itself once the email and password were submitted.  Apparently, port 587 using SSL does not work with Outlook 2011.

Troubleshooting Apple Mail and Outlook




Outlook 2016 for Mac  – 3rd Party Email Clients

What can you import?

Troubleshooting Apple Mail and Outlook






Troubleshooting Apple Mail and Outlook Summary

Much of this email configuring headache can be avoided if the user went away from the abysmal email hosting provider to something like Exchange Office 365 subcription service or if they want free.  Then use Gmail and forward their existing TimeWarner ( account to their new email provider.  No more issues Troubleshooting Apple Mail and Outlook. Fin. The end.

Troubleshooting Apple Mail and Outlook



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