Ron from Long Valley, NJ writes:
I’m running the desktop version of Outlook 2007 and Windows 7. I have years of emails saved in folders and subfolders that I want to keep. I want to start working in the cloud with online Outlook.com. I did a lot of searching but can’t find a way to transfer the emails from my desktop to my account on Outlook.com. Can you help?
Migrating your local Outlook data to Outlook.com mailbox is pretty easy. Here’s how.
Using Outlook 2007 to access an account, you can move your e-mail, contacts, task and calendar information to another account. But before anything else, you first need to back up the data in one account to a Personal Folder (.pst) file to be imported later on the other account.
In Outlook, click File and select Import and Export. At the Import and Export Wizard dialog box, do the following:
- Under Choose an action to perform, select Export to a file, and then click Next.
- On the Export to a File page, select Personal Folder File (.pst), and then click Next.
- On the Export Personal Folders page, under Select the folder to export from, select Mailbox -<user name>. Select the Include subfolders check box, and then click Next.
- On the Export Personal Folders page, in the Save exported file as box, note the location where the backup.pst file will be created. By default, it’s C:\Users\<user name>\AppData\Local\Microsoft\Outlook\backup.pst. Under Options, select Replace duplicates with items exported, and then click Finish.
- On the Create Microsoft Personal Folders page, click OK to create a .pst file. If you want, set a password to protect the .pst file, which will be named backup.pst. A password isn’t required.
Now that you have a pst. of your files, it’s time to move that data to the account of your choice (in this case your Outlook.com account)
- Connect to the account you want to move the data to using Outlook 2007 or Outlook 2010.
- In Outlook, click File, and then click Import and Export.
- In the Import and Export Wizard dialog box:
- Under Choose an action to perform, select Import from another program or file, and then click Next.
- On the Import a File page, select Personal Folder File (.pst), and then click Next.
- In Import Personal Folders, under File to import, locate the backup.pst file you created. Under Options, select Replace duplicates with items imported, and then click Next.
- In Import Personal Folders, under Select the folder to import from, select the top node. Select Include subfolders, select Import items into the same folder in, and then select the top node of your mailbox (Mailbox – <user name>). Click Finish.
Note: If you have lots of data in your mailbox, this may take hours. Make sure that you don’t shut down Outlook, and make sure you’re connected to the destination account while the upload happens.
- Configure you Outlook.com account in Outlook via the Outlook Hotmail Connector.
- Install Outlook Hotmail Connector. After installing, you will be asked to configure a Hotmail account in which you can supply with your @outlook.com address.
- If you already have the Outlook Hotmail Connector installed, choose to add a new account but to configure it manually. You’ll now have the option to select the type of account that you want to add. When you select “Other”, the Outlook Hotmail Connector can be chosen as the account type. Check http://www.msoutlook.info/question/707  for more info.
Manually select the Outlook Hotmail Connector to add an Outlook.com account (click on the image for the full dialog).
In the Hotmail Connector dialog, fill out your @outlook.com address.
Once configured, you can now move items and folders from your current mailbox to Outlook.com mailbox.
If the drag and drop method in moving folders won’t work for you, you can right click on a folder and choose Move Folder.
Default mail folders like Inbox and Sent might give you a hard time moving them. You must select all their items (Ctrl + A) and then move them to their corresponding folder in your Outlook.com mailbox.
(n.d.) MSOutlook.info. Migrating Outlook pst-data to Outlook.com. Retrieved April 13, 2013, from http://www.msoutlook.info/question/765 
(n.d.) Microsoft Corporation. Use Outlook to Move Data Between Accounts. Retrieved April 13, 2013, from http://help.outlook.com/en-PH/140/dd401503.aspx