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10 Tech How-To

Transfer Outlook Express Mail to Outlook or Windows Live Mail

Guide 10-15784 · Updated · Step by step

This guide walks you through moving your emails, contacts, and folders from Outlook Express (OE) to either the classic Windows Live Mail or the modern Outlook desktop app. You’ll need access to the old computer or a backup of its data files, and a destination computer with the target email program installed. The process involves exporting from OE, copying the data files, then importing them into the new client.

What You’ll Need

  • The original computer with Outlook Express still installed and able to open.
  • A blank USB drive, external hard drive, or network share with enough space for your mail (typically a few hundred MB to several GB).
  • The destination computer with Outlook or Windows Live Mail already installed.
  • Your email account settings (incoming/outgoing server names, port numbers, and your password) if you plan to set up the account fresh in the new program.

Step-by-Step

  1. Open Outlook Express on the old computer. Launch the program and wait for it to fully load. If it asks about making it the default mail client, click No or Cancel.
  2. Export your mail from Outlook Express. Go to File > Export > Messages. Choose Microsoft Outlook Express 5/6 as the format, then click Next. Select All folders (or pick specific ones), and click Next. Browse to a folder on your USB drive or local disk, give the file a name like OE_Backup, and click Save. The export creates a single .eml file that actually contains all messages. Click Finish when done.
  3. Export your contacts. Go to File > Export &em; Address Book. Choose Text File (CSV) and click Export. Save the CSV file to the same USB drive. If you prefer, you can also export as a Windows Address Book (.wab) file, but CSV is more universally importable.
  4. Copy the exported files to your USB drive. If you saved them directly to the drive, skip this step. Otherwise, copy the .eml and .csv files to the USB drive.
  5. Move the USB drive to the destination computer. Plug it in and note the drive letter (e.g., E:).
  6. If you’re using Windows Live Mail:
    1. Open Windows Live Mail.
    2. Go to File > Import > Messages.
    3. Choose Microsoft Outlook Express 5/6 as the format, then click Next.
    4. Select Import mail from an OE store directory and click Next.
    5. Browse to the folder where you saved the .eml file (it should be a folder, not the file itself). If you exported correctly, OE created a folder with subfolders. Select that folder and click Next.
    6. Choose All folders and click Next. The import will run and show a progress bar.
    7. After it finishes, click Finish. Your mail appears under Imported Folders.
  7. If you’re using the modern Outlook (Microsoft 365 or Outlook 2019/2021):
    1. Open Outlook.
    2. Go to File > Open & Export > Import/Export.
    3. Choose Import from another program or file, then click Next.
    4. Select Outlook Data File (.pst) and click Next. But wait – Outlook cannot directly import the OE .eml file. You first need to convert it. The simplest way is to import the .eml into Windows Live Mail (as above), then export from Live Mail to a .pst file? Actually, Windows Live Mail cannot export to .pst directly. Instead, use the following workaround:
    5. Install Windows Live Mail on the destination computer (if not already). Import the OE mail into Live Mail as described in step 6.
    6. Then, in Live Mail, go to File > Export &em; Messages and choose Microsoft Exchange or Outlook – but this option may not exist. The reliable method is to use the free tool OE-Mail Recovery or DBX to EML converter to convert the .dbx files directly to .eml, then import those into Outlook using the Import from another program or file > Outlook Data File (.pst)? Actually, Outlook can import .eml files individually via drag-and-drop, but not as a batch. The easiest is to use the built-in Import/Export and choose Import from another program or file, then select Outlook Data File (.pst) – but you need a .pst. So the practical route is:
    7. Use the free utility DBX to EML Converter (search online) to convert your OE .dbx files to .eml files. Then, in Outlook, create a new folder, and drag all the .eml files into it. They will be imported as individual messages.
    8. Alternatively, if you have access to an old version of Outlook (2003/2007), you can import the OE store directly via File > Import &em; Internet Mail and Addresses. But for modern Outlook, the drag-and-drop method is the most straightforward.
  8. Import your contacts. In Windows Live Mail, go to File > Import > Contacts and choose CSV. Browse to your .csv file and map the fields. In Outlook, go to File > Open & Export > Import/Export, choose Import from another program or file, then Comma Separated Values, and follow the wizard.
  9. Set up your email account in the new program. If you haven’t already, add your email account to Outlook or Windows Live Mail using your email provider’s settings. This ensures new mail flows into the same inbox.

Common Mistakes

  • Exporting to a file instead of a folder: Outlook Express export actually creates a folder with .dbx files inside, not a single file. If you try to import a single .eml file, it won’t work.
  • Skipping the contacts export: Many users only export messages and forget their address book, losing valuable contact info.
  • Using the wrong import option: In Outlook, choosing “Import from another program or file” and then “Outlook Data File (.pst)” when you have a .dbx file will fail.
  • Not checking for folder hierarchy: The import may flatten your folder structure. Be prepared to reorganize folders after import.

Tips

  • Before exporting, clean up your OE mailbox: delete junk and large attachments to reduce the file size and speed up the process.
  • If you have a lot of mail, the export can take a while. Be patient and don’t interrupt it.
  • Keep the original .dbx files as a backup until you’ve verified everything imported correctly.
  • For the modern Outlook, consider using the free tool DBX to EML Converter – it preserves folder structure and metadata better than manual dragging.
  • If you’re moving to a new computer, you can also copy the entire OE store folder (usually C:\Documents and Settings\[User]\Local Settings\Application Data\Identities\{GUID}\Microsoft\Outlook Express on XP) and then import that folder directly in Windows Live Mail.

Troubleshooting

  • Import fails with “The file is not a valid Outlook Express store”: This usually means you selected the wrong folder. Make sure you select the folder that contains the .dbx files, not the parent folder.
  • Mail appears but folders are empty: The export may have missed some folders. Re-export, making sure to select “All folders” and that the destination folder is writable.
  • Contacts don’t import: The CSV file may have column headers that don’t match. In the import wizard, manually map the fields (e.g., First Name, Last Name, Email).
  • Outlook shows “Cannot start Microsoft Outlook” after import: This is rare, but if the import corrupted your profile, run Outlook with the /safe switch (hold Ctrl while clicking the icon) and repair the profile via Control Panel > Mail.
  • Windows Live Mail says “The import could not be completed”: Close all other programs, ensure the USB drive is not write-protected, and try again. If it persists, copy the OE store folder to the local hard drive first, then import from there.

Frequently Asked Questions

Can I transfer Outlook Express mail to Outlook without Windows Live Mail?

Yes, but it’s more involved. You need to convert the .dbx files to .eml using a third-party converter, then drag them into Outlook. Alternatively, you can use an old version of Outlook (2003/2007) that supports direct import from OE.

Will the folder structure be preserved?

In Windows Live Mail, yes, it usually preserves the folder hierarchy. In modern Outlook, if you use a converter that outputs .eml files in a folder tree, you can preserve it by dragging the top folder into Outlook. Otherwise, you may need to recreate folders manually.

What about email attachments?

Attachments are included in the messages and will be transferred as part of the import. They appear as normal attachments in the new program.

Do I need to set up my email account again?

Yes, the import only brings over messages and contacts, not account settings. You’ll need to add your email account to the new program using your provider’s incoming/outgoing server settings.

Can I transfer from Outlook Express on Windows 98/2000?

Yes, the process is the same, but you may need to copy the store folder manually because those older systems don’t have USB drivers built-in. Use a network share or floppy disk for small amounts of data.

Is there a way to import directly from a .dbx file in modern Outlook?

No, modern Outlook does not natively read .dbx files. You must convert them first or use Windows Live Mail as an intermediary.

Related

General steps for current mainstream versions; menus can differ by device and version. See the disclaimer or report an error.

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