Migrating From Windows Live Mail to Microsoft Outlook

I was working this week with a client who’d just bought a new laptop and needed assistance with setting it up. Her previous laptop had originally been a Windows 7 computer and had been upgraded to Windows 10 a number of years previous.

Because the old laptop had originally been running on Windows 7, this lady was still using Windows Live Mail as her email client. However, she had purchased a Microsoft 365 license with her new computer and wanted to use Microsoft Outlook to handle her emails. Unfortunately, Microsoft doesn’t make it easy to migrate from Windows Live Mail to Microsoft Outlook. In fact, without the assistance of an IT support professional, it would have been just about impossible for my client to make the switch without losing her old emails.

Unable to Import Emails Into Microsoft Outlook

You’d imagine that Microsoft would have implemented the required functionality in Microsoft Outlook to facilitate import of emails from the free email clients in their own Windows operating systems. Windows XP used Outlook Express, Vista used Windows Mail, Windows 7 had Windows Live Mail, Windows 8 had Mail, and Windows 10 has Windows 10 Mail.

Unfortunately, the functionality required isn’t provided and Outlook only permits the import of a .pst file which is its own proprietary file format. Other email clients do facilitate the import of email from other applications and formats. My own personal favourite is em Client which can import email and folders from Microsoft Outlook, Outlook Express, Windows Live Mail and others.

Before going any further, let’s take a look at the two email protocols supported by Windows Live Mail.

Email Protocols

POP3: Older email accounts were typically configured using POP3. This was appropriate for a time when people would have been accessing their email using a single device only. The basic principle is that emails are collected from the mail server and delivered to the computer. A copy of the email can then be left behind on the server, or it can be deleted. There is no synchronisation between the mail server and the email client.

IMAP: POP3 has now been largely replaced by IMAP. In this scenario, emails on the client device are synchronised to the mail server. This means that the email client will display a copy of what is on the server, including any folders created. This is useful when more than one device is used to access emails as the email is synchronised across all the devices. As a result, any change implemented on an email client is reflected on the server and on any other devices.

Email Storage Folders

If an email account has been configured using IMAP in Windows Live Mail, then it may not even be necessary to import the emails into Microsoft Outlook. This depends on whether any email storage folders are located offline or online in Windows Live Mail.

If storage folders have been created online, ie they are located on the email server, then an email client configured to use IMAP will automatically download these folders when it synchronises to the email server. If on the other hand any folders created are offline, ie on the local computer only, then a different approach will be required. If the folders are in fact offline, they can be moved online simply by dragging and dropping them within the email client. Then when synchronisation takes place, they will be uploaded to the email server. From there they can be synchronised to another device using IMAP.

Exporting Emails and Folders From Windows Live Mail

Returning to the task at hand, unfortunately my client’s email had been configured using POP3, not IMAP, and her email storage folders were offline. This meant that those folders would need to be imported into Microsoft Outlook, as they couldn’t be synchronised automatically. Since it’s not possible to import from Windows Live Mail into Microsoft Outlook, it was necessary to instead first export the emails from Windows Live Mail. It is possible to do this as email can be exported in Microsoft Exchange format, which is supported by Microsoft Outlook.

I began the process of exporting the emails from Windows Live Mail by selecting the option to export email messages to Microsoft Exchange format. This essentially means packaging all the emails and folders from Windows Live Mail into a .pst file suitable for import into Outlook. Unfortunately, as soon as I attempted this, I was presented with an error message stating, ‘The export could not be performed. An error occurred while initializing MAPI.’


MAPI stands for Messaging Application Programming Interface and is a Windows program interface which enables the sending of email from within a Windows application. However, in order for MAPI to function, it requires the installation of an email client which includes a MAPI server. In our case this would be Microsoft Outlook. However, Microsoft Outlook hadn’t been installed on my client’s old laptop since she hadn’t been using a Microsoft Office product which included Outlook.

In order to provide the MAPI functionality, I proceeded to install Microsoft Office on the old laptop. A license wouldn’t be required since we would be at the beginning of the 30-day trial period. I installed Microsoft Office 365 and configured Microsoft Outlook as the default email application, only to find that the error was still occurring when I attempted the export.

Successful Export of Emails

It turns out that a 32-bit installation of Outlook is required to accomplish the export. I uninstalled Microsoft Office and, in order to be sure that I would be using a version which would be compatible, I installed 32-bit Microsoft Office 2007 and configured this as the default email application.

Having launched the export from Windows Live Mail once again, it worked perfectly, and the emails and folders appeared in Microsoft Outlook 2007. I was then able to locate the .pst file which had been created and copy it to the new computer. I then imported this into the recently installed Microsoft 365 version of Microsoft Outlook and my client’s folders and emails appeared.

Migration of Contacts

The only remaining task was to also migrate my client’s email contacts. This was relatively straightforward as it was possible to export the contacts from Windows Live Mail to a .csv (comma separated values) file. This could then be imported into Microsoft Outlook on the new computer. The only hurdle to overcome with this import was that I first had to open the contacts file in Microsoft Excel and then resave the .csv in order for it to be imported into Outlook correctly.

Tidy-Up Required

Following this rather complex procedure, my client was now able to view her current and previous emails and folders in Microsoft Outlook on her new computer. Although all the folders had been imported correctly, a tidy-up was necessary since, after adding the email accounts, old emails were downloaded for a second time from the email server. As it turned out, her POP3 settings had been configured to leave all emails on the server, so although she was deleting and filing emails on her laptop, everything was being left untouched on the server.

The author runs a local computer repair and IT support business in Brisbane, Australia.

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