If you’re moving to Outlook.com from Gmail, Hotmail, or any other email service, you may want to copy or move all of your old email into the new account. There are probably a number of ways to do this, including at least one that is automated.

Which method you use may depend in part on which email service you’re moving from, how much email you wish to import, and how convoluted a message folder structure you maintained on your old account. Here are a couple of approaches I’ve experimented with.

Automated email import

Like other webmail providers such as Gmail and Yahoo!, Microsoft has partnered with TrueSwitch to provide a free, automated wizard for moving your old email (and some other data) from a previous account to an Outlook.com (or Hotmail) account. You can access the Outlook.com and Hotmail TrueSwitch wizard here.

trueswitch
Using the wizard is simple enough: Enter your previous webmail service’s email address and password, your Outlook.com email address and password, and then select which items you’d like to import. For purposes of this article, we’re just selecting email messages, but you can also import your contacts (and, apparently, your calendar, though this is grayed out for me).

Email importing happens up in the cloud, so you won’t need to wait for it to complete, and TrueSwitch will send you an email message when that happens. Before then, however, you’ll receive some helpful emails letting you know that the import is happening and providing you with status updates.

status

For you folder junkies, yes, TrueSwitch will maintain your folder hierarchy. If there are any duplicate folders, a new version of the folder will be created at your Outlook.com address (like “Archive 2” if there’s an Archive folder at both locations).

The manual approach: Email client + copy and paste

If you don’t trust the automated approach—and, honestly, I’d be nervous about importing my mammoth Gmail archive this way—or simply want to be more hands-on with the email import, there are probably a number of ways to make that happen. But one I’ve tried, while time consuming, is to simply drag and drop emails between and old and new accounts using a Windows email client that’s been configured for both. In the past, I’ve done this with Windows Live Mail (which is still available as part of Windows Essentials), so I’ll fire that up as an example.

(Note: Even if you never intend to use Windows Live Mail again, this may still be worth doing just to copy over your old emails. It’s a one-time thing.)

First, of course, you must configure the email application for both accounts. In Live Mail, these accounts appear in the Folder pane in the left of the application while Mail is selected. (Contrary to its name, Windows Live Mail also lets you access contacts, appointments, and other data.)

folder

Select the folder you’d like to import in the source account—the account from which you will be importing, or copying, email—and the messages it contains will display in the Message list.

In the destination account—the account to which you will be importing, or copying, email—create a folder, if needed, to contain the incoming messages. For example, if you’re copying over email from an Archive folder in the source account, you may want to create and use an Archive folder in the destination account as well.

In the source account’s folder, select the emails you want to copy. (To select all of them, just select one and then tap CTRL + A; Outlook will report how many messages are there in its blue status bar in the bottom left of the application window.)

Then, right-click the selected messages and choose Copy to folder. In the Copy window that appears, select the correct folder in the destination account. Then, click OK.

copy

The selected messages will be copied between accounts. Obviously, this process can be slow if you’re copying numerous messages, so you might consider doing this in batches or letting it run overnight for longer-lasting accounts.

This approach isn’t super-efficient. In fact, it’s sort of a bare knuckles way of making this happen. But again, if you really want to ensure that your old email is in your new account, this will do the trick.

I am curious if there’s a more efficient way, however. If you have any ideas about this, please let me know.