Effortlessly Migrate Windows Live Mail to Office 365

Updated on April 04, 2024 by Deepika Singh

Following the pandemic, there has been a notable shift from traditional email services to cloud-based alternatives, leading to a surge in Windows Live Mail to Office 365 migration. Through extensive research and testing, we'll explore the most effective methods to migrate Windows Live Mail to Office 365. Furthermore, we'll examine the advantages of Office 365 over Windows Live Mail. Stay tuned until the end to discover insights into the Regain EML to Office 365 Migrator.

Why Office 365 is better than Windows Live Mail?

Office 365, a Microsoft product, operates as a cloud-based service primarily catering to email, calendar management, notes, and other essential items. Its array of features serves as a compelling incentive for users to transition from Windows Live Mail to Office 365. Let's explore some key reasons why Office 365 stands out:

  • Users prefer using the Microsoft 365 webmail service due to its accessibility from anywhere at any time. It only requires account credentials for access.
  • Office 365 is scalable, allowing users to easily upgrade and enhance quota space and other business-oriented features as needed.
  • Many technical users recommend and utilize Office 365 for its robust security features. Microsoft, being a renowned tech giant, enjoys trust among users.
  • Microsoft 365 offers not only a cloud-based email service but also provides access to productivity applications online, including Word, Excel, PowerPoint, OneNote, SharePoint, and OneDrive.

Manually Migrate Mailbox of Windows Live Mail to Office 365

Before initiating the steps, users must comprehend that there isn't a direct pathway to migrate Windows Live Mail to Office 365. The process entails multiple steps. Moreover, users must ensure that their Windows Live Mail is free from errors. Issues such as 0x800ccc90, 0x800ccc79, etc., must be addressed before commencing the migration process. The steps to convert Windows Live Mail to Office 365 are as follows:

  • Step 1: Export Windows Live Mail Data
  • Step 2: Convert Outlook Data to PST
  • Step 3: Upload PST to Office 365

Let’s explore the steps to manually migrate Windows Live Mail to Office 365.

Step 1: Export Windows Live Mail Data First, you need to export all the Windows Live Mail data using Microsoft Exchange. The steps are as follows:

  1. Launch Windows Live Mail and navigate to File >> Export Email >> Export Messages.
  2. Choose a program like Microsoft Exchange and click the Next button.
  3. A pop-up message will appear, stating that this action will export messages from Windows Live Mail to Microsoft Outlook or Exchange. Click OK to proceed.
  4. Set Outlook as the profile name and click OK.
  5. Select all or the desired WLM folders to export and click OK.
  6. Wait for the export process to complete and then open Outlook to verify and synchronize the exported emails.

After successfully exporting the Windows Live Mail data you can proceed to the next step.

Step 2: Convert Outlook Data to PST After exporting the Windows Live Data you have to convert that data to PST file format. The steps are as follows:

  1. Begin by launching MS Outlook and selecting File >> Open & Export >> Import/Export.
  2. Next, opt for the Export to a file option and proceed by clicking Next.
  3. Choose Outlook Data File (.pst) and click Next.
  4. Select the folders imported from Windows Live Mail that you wish to export.
  5. Navigate to the desired location to store the resulting PST file.
  6. Click OK to generate the PST file containing the data.

After following the steps mentioned above you will easily convert the Windows Live Mail data to PST. Now you can proceed to add the PST files to Office 365.

Step 3: Upload PST to Office 365 Two primary methods exist for adding PST files to Office 365. These methods are outlined below:

In the section below we will explain the steps to use the Network upload method.

  1. Install the Azure AzCopy Tool and obtain the SAS URL.
  2. Generate the PST import mapping file.
  3. Subsequently, set up a PST import job.
  4. Apply filters to facilitate the import of PST files.
  5. Initiate the PST import job to commence uploading data.

After completing all three steps, you can successfully migrate Windows Live Mail to Office 365. However, it's important to note that the manual approach has several limitations, some of which are outlined below.

Limitations of Manually Exporting WLM to Office 365

  • Complexity: Manual migration can be complex. Additionally, it requires a good understanding of email protocols and technical settings. Non-technical users may find it difficult to navigate the process effectively.
  • Risk of Data Loss: Manual methods may not transfer all data accurately. Furthermore, this leads to potential data loss or incomplete migration, especially with large mailboxes.
  • Time-Consuming: Manual migration is a time-consuming process, particularly for large volumes of data or multiple user accounts. This can disrupt productivity and strain IT resources.
  • Compatibility Issues: Compatibility problems may arise when migrating between different email clients and versions, potentially causing email formatting issues or data corruption.
  • Authentication Challenges: Ensuring correct login credentials and authentication methods for each account can be challenging, increasing the risk of failed migrations.
  • Lack of Automation: Manual migration lacks automation, requiring users to perform repetitive tasks for each mailbox. This increases the likelihood of errors and prolongs the migration process.
  • Limited Data Validation: Manual methods often lack robust data validation checks, making it difficult to verify the integrity of migrated data and increasing the risk of unnoticed errors.

Automated Method to Migrate Windows Live Mail to Office 365

The process to migrate Windows Live Mail to Office 365 can be easy if you use the IT Experts Recommended Regain EML to Office 365 Tool. The process is easy. Simply download and install the EML to Office 365 Migration software on your system. With just a few simple steps, you can effortlessly import all emails and attachments into your Office 365 account.

Steps to Migrate Windows Live Mail to Office 365

  1. Install and run the Regain EML to Office 365 Migration Tool as an administrator.
    EML to Office 365 Tool
  2. Click on the Browse button to search and add the EML files to the software wizard.
  3. Once the scanning process is finished, you can choose the desired files or folders from the tree structure format.
    scanning process
  4. Now, click on Office 365 to migrate WLM to Office 365.
  5. Enter your Office 365 credentials and click on the Connect button.
    Office 365 credentials
  6. Finally, you can download a detailed log report of the conversion.

Advantages of Using Automated Tool

There are many advantages of using the Regain EML to Office 365 Migration Tool. Some of them are as follows:

  • Easily migrate multiple EML files or folders to your Office 365 account with just a few clicks.
  • Export EML Files to Office 365 while preserving all email properties such as Contacts, Calendar, and Attachments.
  • Maintain the original files and folder hierarchy throughout the migration process.
  • Selectively move specific emails into your Office 365 account.
  • Ensure 100% accurate and error-free migration.
  • Compatible with all EML-based email clients including Windows Live Mail, Windows Mail, Thunderbird, Outlook, Outlook Express, etc.
  • Generate a comprehensive migration report for reference.
  • User-friendly interface for easy navigation.
  • Take advantage of the Free Trial Version to save up to 30 emails per folder at no cost.


In this article, we have discussed the practical methods to migrate Windows Live Mail to Office 365. Additionally, we highlighted the benefits of using Office 365. To fully benefit from Office 365, you need to switch from your current email client to Office 365. Migrate from Windows Live Mail to Office 365 using Regain EML to Office 365 Migration Tool to ensure a smooth transition.


Q1: Is it still possible to utilize Windows Live email?

Ans: No, the Windows Live email service is no longer operational. Microsoft ceased the service in 2013 and advocated for users to transition to Outlook.com, now integrated into the Microsoft 365 suite of productivity tools.

If you previously had a Windows Live email account, it's likely been migrated to Outlook.com. You can access your email by logging in with your Windows Live email address and password. However, new email accounts cannot be created with the Windows Live domain.

Q2: What is the difference between Outlook and Windows Live Mail?

Ans: While Windows Live Mail and Outlook both offer email and calendar functions, Outlook boasts additional features like task management and note-taking. Unlike Windows Live Mail, Outlook features a programming interface allowing for the use of VBA code for customization, both within Outlook itself and from external applications.

Q3: Which is the best Migration tool for Windows Live Mail?

Ans: While numerous migration tools exist online, discerning the most suitable one for your needs can pose a challenge. We suggest starting with the 'Regain EML to Office 365 Migration tool' and evaluating whether it aligns with your requirements. We are confident that you will find it to be a wise choice.

Q4: Will the folder structure and hierarchy be maintained during the migration process?

Ans: Professional migration tools are engineered to uphold the original folder structure and hierarchy of your Windows Live Mail data, guaranteeing that your emails stay organized within Office 365.