How To Fix Your Broken Email

What would you do if you or someone you love suddenly couldn’t send emails anymore? Don’t panic! It’s time for emergency email 101.

Last week, on the day the geek world was digesting Apple’s newest must-have tech announcements, I received a phone call from my father.

Surely he had heard reports of the iPad mini, or was blown away by the concept of the new iMac’s Fusion Drive. Maybe he wanted to discuss the controversial issue behind launching the killer iPad 4 only six month’s after its predecessor.

He normally would want to know all about this.
But not this time. He had something much more important to discuss.

His email had stopped working.
And now he was cut off from the world.

Of course, I am his home IT support.
So I attached my geek pocket protector to my shirt, rolled up my short sleeves, put on my thick black glasses and sat down at my computer.
Now what?

Fortunately, I was able to remotely screen share with his iMac via iChat and began diagnosing what was sure to be an easy fix.

Unfortunately, I quickly realized I didn’t know what it was.

Email 101
The problem with email is it’s usually a ‘set it and forget it’ tool. When it stops working, your memory may not be so clear on how it actually works.
Here’s a quick refresher…

You’ve normally got two paths to get to your email: web-based and client-based.

Web-Based Email
If you want to use a web-based portal, you simply have to access a working web browser and then remember your username and password.
(Everyone knows that!)
If you don’t, please see my spin-off blog – Never At Home with Tech.
The big benefit to web-based email is you can access it anywhere on any computer, as long as it’s online.

Client-Based Email
Here, your emails get downloaded to your computer, where you can access and work with them on a dedicated application whether you’re online or not.

To successfully use an email client like Outlook and Apple’s Mail program, you’ve got to get some settings right…

The two biggies are:

  • Incoming Mail Server
  • Outgoing Mail Server

These two settings direct your inbound and outbound email traffic to the correct mail servers that manage your emails.

The proper settings depend on whose email platform you’re using. And which version of the application you’re working with.
So the bad news is there isn’t a simple solution that applies to all situations.
The good news is there’s a simple answer. You just need to figure it out!

A Tale of two Email Accounts
My father has two ESPs (Email Service Providers) flowing through his Apple Mail application- AOL and his Apple iCloud account.

Both were broken.

A quick aside about the recent evolution/confusion surrounding Apple’s email addresses:
Once upon a time, they were punctuated with ‘’
Then Apple changed it up with MobileMe and updated their email addresses to end with ‘’
Now… Apple is creating ‘’ addresses.

The good news is all three email address extensions work.
And they will continue to function in the foreseeable future as per this Apple support page-
About email addresses

So back to my father…
Technically, both email accounts weren’t totally dead.
Both were receiving, but not accepting emails.

I went to the Mail Preferences tab to review the settings.
My father had already done some troubleshooting. So I decided to double-check it.
(sorry, Dad)

Dad primarily uses his AOL email. (He’s so old school.)  So I attacked that one first.

Tech Tips for AOL Email Set Up
Here’s how it should look:

  • Incoming Mailer Server =
    (IMAP stands for Internet Message Protocol.
    This email system syncs your local files with the mail server.)
  • Outgoing Mail Server =
    (SMTP stands for Simple Mail Transport Protocol.
    It’s a communications protocol for servers to send/receive emails.)

Seems simple enough, right?

Yes, but you’ve also got a few other settings to contend with.
Here they are:

Under the Advanced Tab for Incoming Mail Server:

  • Port = 143
  • Authentication = Password

Under the Advanced Tab for Outgoing Mail Server:

  • Authentication = Password
  • User Name = Your email address without the ‘’
  • Password = Your correct password (sorry, Dad)

And Select-

  • Use default ports (25, 465, 587)
  • Use Secure Sockets Layer (SSL)

That should do it.
(This AOL support page was useful.)

But it still didn’t work!

Connection Doctor to the Rescue
That’s when I launched Connection Doctor, which you’ll find under the Window drop down. When you do that, the program does a diagnostic to see if both your incoming and outgoing settings are correct. You can tweak them in real time to see if you’re making progress.

When I did this, I noticed that the AOL settings were green, but the outbound iCloud setting was red. That account seemed stuck in an eternal send mode.
So I disabled the iCloud account to see if the AOL email was somehow being affected by an iCloud bottleneck.

I immediately heard the familiar whoosh of a happy AOL email leaving the mother ship.
AOL email was fixed.
One down; one to go.

Tech Tips for iCloud Email Set Up
The iCloud settings were straightforward as well. Take a look below…
(Also, here’s a good Apple Support page on the topic.)

  • Incoming Mailer Server = or just
    (depending on which version of Mail you’re using)
  • Outgoing Mail Server =

Under the Advanced Tab for Incoming Mail Server:

  • Port = 993 (Use SSL)
  • Authentication = Password

Under the Advanced Tab for Outgoing Mail Server:

  • Authentication = Password
  • User Name = Your email address WITH THE ‘@ME.COM!’
  • Password = Your correct password

I hate to admit it, but adding the complete email address for the User Name did the trick. (my bad)


I felt like I had cracked a huge safe.
My father thanked me big time and then went back to watching a Humphrey Bogart movie on AMC.

The Operation was a Success, but…
I should mention that part of my successful diagnostic process was to use my old MacBook Pro laptop as a canary in the coal mine, since that computer also uses Apple’s Mail.
My iMac uses Entourage, which I know needs to be upgraded to Outlook.
(Look for that nail-biting experience in a future post.)

So while I was doing a victory lap in my home office, I took a screen shot of my MBP’s Mail settings and popped it into a test email for my iMac as reference. The email would also serve as a confirming test.

I looked again at Connection Doctor; all lights glowed green.
I clicked the ‘send’ button and heard the satisfying whoosh.

I turned to my iMac and waited for the triumphant arrival… and waited.
Five minutes elapsed.
It never arrived. (seriously)

I checked the MBP’s sent folder, and the email happily stared back at me as successfully sent…
(I felt like the young Scotty in J.J. Abrams’ ‘Star Trek’ when Scotty lost Admiral Archer’s prized beagle during an ill-fated transporter experiment.)

If anyone out there runs across my test email, please let me know!

So I simply tried again.
And this time it worked!

History is Written by the Victors
I suppose every road to home tech success is littered with a few setbacks.

I had fixed my father’s email, and then inexplicably lost one of my own along the way.
The little Winston in me wants to figure out where that email went.
But it was really time to move on. I’ve got bigger tech battles waiting in the wings.

Which leads me back to a simple truth for keeping your home tech humming.
If it works, don’t ask any more questions.