How to Lose your Email while Upgrading from Entourage to Outlook

by Barrett

If you’re still using Microsoft Entourage, it’s really time to make the jump to Outlook for Mac 2011. But watch out! You can end up with double or none of your email!

I’ve been meaning to upgrade my email program from Entourage
(Microsoft’s old email program for Macs)
to Outlook for Mac 2011.

But I’ve been delaying, because any tech upgrade usually comes with risks.
And you know what they say:
“If it ain’t broke, why fix it?”

Well, my old Entourage has been acting a bit glitchy lately.
It’s from Office 2008, before Outlook ran on Macs, but it mimics Outlook’s functionality.
I originally used Entourage back in 2004 on my first iMac to migrate my email when I used a PC at home.
(Please don’t share this secret from my younger days. I’m still a little sensitive.)

So over the past year, Entourage has occasionally crashed on me while sending out emails.
And that’s been kind of frustrating.
‘Cause you’ve got wonder whether the email actually got out or not.

You could pick up the phone to confirm, but that defeats the point of email, don’t you think?
(I hear my father chuckling. He still talks about the glory days of telegrams.)

Don’t Reach out and Touch Someone
Like it or not, email has become an essential communications tool in today’s digital-based society. Without it, you really can’t participate.

You certainly can’t do your job if it involves interacting with people.
Sure, you could make a phone call, but email is so much easier.
I think people actually prefer not using the phone at work if they can avoid it.

It takes too much time.
And it involves interacting with another individual.
How messy is that?
It’s so 20th century.

On the other hand, emails are simple.
More direct.
Plus they leave a record of what you said.
And you don’t have worry about developing or maintaining your interpersonal skills.
(Really, who needed them anyway?)

At home, email has also caused the phone’s popularity to slip.
(Though texting is also a culprit.)

When I’m on the 5:48pm Metro North train out of Grand Central Terminal, a simple text to my wife reporting my ETA is sufficient, don’t you think?

After I get home and boot up the iMac, my email engine is front and center to handle my communications with our global village.
So it had better work!

All Those Wonderful Marketing Deals I Requested
One problem is my email in-box has become a train wreck.
Over the years, it’s filled up with tons of communiqués I really don’t want.

Most of them are marketing emails from companies I’ve volunteered my email address to.
And why have I done that?
At the time, it seemed like an innocuous gesture with the promise of special insider ‘deals’ that would come my way.

These aren’t spam emails, mind you. I’ve asked for them.
It’s time to do some significant unsubscribing.
But that’s another project for another day.

And really, I shouldn’t slough off the blame.
The truth is much of my email is simply a mess of disorganization resulting from years of minimal email maintenance. I should have been slimming things down along the way.

Protecting your Digital Diary
Like going to a long overdue dentist appointment, I knew my email in-box needed serious work, but I always had better things to do.

Finally I decided it was time.
But I was concerned that the upgrade might not go as planned.
I might corrupt the archive and risk losing some of my old emails.

That’s not much a loss for all the marketing muck, but there are plenty of valuable emails to protect for the long term.

Like letters we used to keep.
Remember when people stored their old letters in shoeboxes?
The fact is your old emails represent a sort of organic digital diary for your life.

The Upgrade Begins
To prepare for the migration, I decided I would do a little tidying up and ‘thin out’ the marketing flirtations along with some old emails I didn’t need anymore.
(Why clog up the transfer with useless messages?)

So I sat down and got to work.
In my first pass, I quickly got rid of 1,024 emails.
A third of them had never even been read.


It was a start, but believe me, that barely created a dent.

Then, I loaded Outlook for Mac 2011 onto my iMac.
The new program lives separately from Entourage on your desktop, and there’s no magical merging.
You’ve got to copy all your email over.


There’s a lot online regarding the best way to do this, and believe me there are many hard paths to the finish line.

I chose the easy way.
(Actually, it’s all I could really understand!)

So when you first launch Outlook:

  • Click Import
  • Click Entourage
  • Select all of the boxes regarding the items to import
  • Select Main Identity

That’s it!
The transfer process swiftly began.
I watched as my 5,713 emails imported effortlessly into Outlook.

Within minutes, the process was complete.

I stared in near disbelief at the simplicity of my experience.
Something was clearly not right.

And I was correct.

Attack of the Clones
I looked about the new interface and noticed that Outlook was in the middle of another import process.


I thought we were all done.

I looked closer, and it was downloading a few more messages…
This time from the mail server.
About 4,000 more.


For some reason, Outlook was now downloading all of my messages from my Optimum Online mail server, creating duplicates of most of my emails living locally on my iMac.

There didn’t seem to be a way to stop it.
So I buckled up and went along for the ride…
An hour later, I was the proud owner of almost 10,000 emails.

And how was I to rid myself of these unwelcome clones?

The good news is they all showed up bolded as unread and received within the past hour.
So I resorted the list by ‘Date Received.’
Then, I highlighted them and simply pressed ‘Delete.’

And I watched my iMac reverse course and purge the duplicate
‘History of Barrett.’

(I’m sure the computer was thinking, “silly human.”)

Delete from Server?
I felt like I had dodged a bullet.
Or at least many hours of manually deleting 4,000 emails.
But I was curious. So I went online and did a little research.

My problem seemed to be related to the fact that my Optimum Online email was a POP account instead of IMAP.

But before I tried to figure out what that really meant, I saw that
other users had also experienced similar problems when migrating their messages to Outlook for Mac 2011 for the first time.

I felt vindicated.
Then I got nauseous…

Someone also reported that once you delete the duplicate messages, the server wants to purge both versions.


As long as your Outlook preferences are set to-
‘Never’ Delete Messages off the Server, you’re okay.

So I took a look at my Outlook’s preferences, and, of course, they were different.
These were my default settings, imported from Entourage:

  • ‘Leave a Copy of Each Message on Server’
  • Delete Copies from the Server ‘After Deleting From This Computer’

Bad news.
All my email on the mail server was now-

They only existed locally on my computer.

If I had wanted my messages backed up on the mail server to access remotely through a web interface, I was out of luck.

Oops… I Just Blew Up my Email!
Yes, by upgrading my email to the latest and greatest platform,
I had deleted my entire email archive on the mail server.
(This is why I’m never to eager to tinker with upgrades I don’t have to make.)

The good news is I rarely access my Optimum Online email via web interface, because I always have access to them on my iPhone.

So this loss was largely a meaningless forfeiture.
Except that it served as a Cloud back-up I no longer have access to.
(And you know how much I love back-ups.)

Tech Tip to Avoid Losing all your Email on the Mail Server
Here’s the fix to avoid my sad story and prevent the deletion of your email on your mail server:

Change the ‘Delete Copies from the Server’ option to-
BEFORE you delete your unwanted cloned emails in Outlook.

Only AFTER you purge the duplicates should you change the server’s delete settings back.

See, isn’t that easy?

Today’s Outlook is no longer Cloudy
I suppose the silver lining is my error resulted in some long overdue spring cleaning on the mail server.
Did I really need to save all these emails up in the Cloud?
Is each of them so critical to my future memoirs?
(currently not in development)

I should thank Microsoft and Apple for helping me to purge all this unnecessary content!

Wait, I’ve got go. My father needs me.
My doorbell just rang.