You heard all the wonderful things I said about cloud computing in the last article, and I mentioned that the transition process – while easy – takes a bit to explain how it’s done.

This article explains how it’s done in easy-to-understand terms.

We’ll be using Outlook Express 6 as our example. There are many who use this program as it comes free with Windows XP and feel that they’re stuck with it. No, you’re not. You can migrate all your mail over to Gmail or Hotmail easily. All it takes is a minimal amount of setup and a small amount of your time.


Why would you do this?

For the following reasons:

  1. Backing up e-mail out of Outlook Express is a pain. You either have to use a full corporate paid version of Outlook or drag/drop the mail outside the client into a folder. Either way is bad. It has never been easy to backup mail out of OE. Moving to a new e-mail account is the easiest safest way.
  2. Outlook Express is old and obsolete. You can’t flag spam in it and in order to bring it to the features of other current clients you need to spend money on add-ons for what was free software. Don’t bother. Time to ditch it.
  3. Outlook Express has no ability to sync anything natively. The address book is an island unto itself as is the rest of the features. Nowhere in Outlook Express is there anything natively in the client that will allow it to sync to a web-based mail service. As said above, this is old obsolete software.

Outlook Express, simply put, is very close to being a dinosaur – meaning close to extinction. Technically speaking it’s already extinct since the launch of Windows Vista in January 2007. The only reason it’s still used is because at the time of this writing most people still use XP.

Get a Gmail account

Easy enough. Go to and sign up.

Enable your Gmail account to be IMAP enabled

Click on Settings then the Forwarding and POP/IMAP tab and tick Enable IMAP then click Save Changes.

Looks like this:


Configure your Gmail account in Outlook Express

I covered this in great detail in this article:

Follow the steps there and your Gmail account will be active in your Outlook Express mail client.

What your Outlook Express should look like (roughly)

This is the hard part (but not really).

If all goes well you’ve got your local POP account using “Local Folders” and your Gmail account in its own set of folders.

It looks something similar to this:


To answer the question, “Why does Outlook Express insist upon putting all POP accounts in Local Folders only?” – the answer is because it was designed that way. It’s a limitation of the software (and one of the many reasons why it’s a dinosaur).

Enable the size column

You will notice in the screen shot above that I have the Size column enabled that shows me how big each e-mail I have is.

If you don’t see this, click View (at the top) then Columns and check off Size.

It looks like this:


It is absolutely paramount that you have this enabled because you will be using it a lot when moving mail from POP to Gmail.

Click the size column to sort from smallest to largest

When you click the size column you are sorting the mail by size. If you click it once, the arrow next to the word Size will point down. Click it again and it will point up. You want it facing up because that puts the smallest mails on top and the largest on the bottom.

It looks like this:


Why are we doing this? Because it’s easier to move the smaller mails first as they obviously will upload/download faster.

Where will we be moving mail to?

Although this should be readily obvious I’m going to state it anyway just to avoid any confusion.

Don’t move any mail yet. This is just a primer to let you know where mail will be moved to.

Notes: “Local Folders” refers literally to what is shown as Local Folders in Outlook Express. “Gmail account” refers to whatever your Gmail account is named within Outlook Express. If you chose the default name, it’s most likely labeled unless you changed it. Either way, it’s very easy to distinguish the difference between what’s “Local” and what’s “Gmail” just from a quick glance.

Again, please do not move any mail yet. You’ll understand why in a few moments.

Local Folders – Inbox moves to Gmail account – Inbox

Local Folders – Outbox has no mail that needs to be moved.

Local Folders – Sent Items moves to Gmail account – Sent Mail

Local Folders – Deleted Items has no mail that needs to be moved unless you specifically want to move it. If you do, it would go to Gmail Account – Trash

Local Folders – Drafts moves to Gmail account – Drafts

What about folders?

If you use custom created folders under Local Folders, you will be dragging and dropping all that mail into Gmail Account – Inbox and then setting up what are known as “labels” later in Gmail itself via a web browser at

Tips when moving mail from POP to Gmail to make it easier to assign labels:

You can opt to sort by From instead of Size. You can move over e-mails from specific recipients, head into Gmail in a web browser, label them, then go back to Outlook Express and head to the next batch. If you use folders, this is the easiest way to do it.

How long will moving the mail take?

This depends on three things:

  1. Your internet connection speed.
  2. How much mail you have to move.
  3. How large the mail is you have to move.

For most people, moving 1000 mails or less will take about 1 hour. However if you have many e-mails with large attachments, 2 to 3 hours.

Why so long? Because uploads always take longer than downloads and are “throttled” by design of your ISP.

Okay, let’s move some mail

The suggested way of moving mail is to do the following:

  1. Move the mail out of your custom folders (if any) first.
  2. Move the the mail out of your old inbox to the new one next.
  3. Move your Sent Items to the new Sent Mail last.

If sorting by Size (smallest-to-largest)

  1. Choose the folder you want to move mail from (an old custom folder, the old inbox, etc.)
  2. Select the topmost mail by clicking on it.
  3. Press and hold your SHIFT key.
  4. Press the down arrow on your keyboard and highlight 50 e-mails so they are highlighted.
  5. Once highlighted, click Edit (at the top) then Move to Folder.
  6. Select the folder the mail is to be moved to.

If we were moving mail from the old inbox to the new Gmail inbox, that looks like this:


Note the inbox on the Gmail account is highlighted. That is where the mail is going.

During the move, you will see a status similar to this:


IMPORTANT NOTE: For larger e-mails with file attachments, Outlook Express will appear to be “stuck”. It is not stuck. The mail is just taking time to upload to the Gmail mail servers.

Why only 50 e-mails at a time?

This is to avoid server time-outs on the Gmail side. If you’re feeling brave you can do 100 at a time but I would not recommend it.

What about larger e-mails?

For the e-mails you have that are over 100k each, move 25 or less at a time. For a mail server this is a lot of data you are transferring.

Final Q & A

Can I use still Outlook Express even after I move my mail to Gmail?

If you choose you can continue to use Outlook Express with Gmail, however this is not recommended because the flag-spam function is completely disabled as are labels and other major features.

Get used to using mail via Believe me when I say you will like it a whole lot more (and it’s notably faster than using a client besides).

How do I get new mail arriving to my old account into Gmail without migrating?

This is easily done by configuring your Gmail account to check your old POP account for new mail and delivering it straight to your Gmail account.

In Gmail, click Settings then Accounts.

Look for Add another mail account.

It looks like this:


You will need to know your incoming and outgoing mail server addresses plus your username/password you use to access your old mail. However you know this information already (otherwise how could you have set up your old mail in the first place?) so it should be easy to get.

Once this is set up, Gmail will check your old mail account routinely for new mail and deliver it to your Gmail inbox.