Windows Live Mail to Office 365 Migration

Updated on November 09, 2023 by Deepika Singh

In today's fast-paced world of information and technology, the way we communicate and manage our emails has evolved significantly. Gone are the days of standalone email clients like Windows Live Mail, which served as a reliable companion for many Windows users over the years. In their place, cloud-based productivity suites like Office 365 have become the new norm, offering an array of powerful tools and seamless collaboration features.If you're still relying on Windows Live Mail but are ready to make the leap to Office 365, you're in the right place. This blog post will be your guiding light through the migration process, ensuring that you can seamlessly transition from the old to the new without missing a beat.

We'll explore the reasons behind this migration, the benefits of moving to Office 365, and, most importantly, the step-by-step instructions on how to make the transition as smooth as possible. Whether you're an individual user, a small business owner, or an IT professional responsible for a larger migration project, this guide will equip you with the knowledge and tools needed to ensure a successful transition.

Related Software: Looking for EML to PST Converter Tool

Reasons Why Users Move Windows Live Mail to Office 365

Migrating from Windows Live Mail to Office 365 is a decision driven by several compelling reasons. Here are some of the key motivations behind this shift:

Enhanced Collaboration: Office 365 offers a suite of tools, including Microsoft Teams, SharePoint, and OneDrive, that facilitate seamless collaboration among users. This collaborative environment is essential for modern workspaces where teams often work remotely or across different locations.

Access Anywhere, Anytime: With Office 365, users can access their emails, documents, and applications from anywhere with an internet connection. This flexibility is crucial for businesses and individuals who need to stay productive while on the go.

Scalability: Office 365 is highly scalable, making it suitable for both small businesses and large enterprises. You can easily add or remove users, adjust your subscription, and scale your resources to match your organization's needs.

Regular Updates and New Features: Microsoft constantly updates and enhances Office 365 with new features, improvements, and security updates. This ensures that users have access to the latest tools and capabilities without the need for manual software updates.

Integration with Other Microsoft Services: Office 365 seamlessly integrates with other Microsoft services and applications, such as Azure Active Directory, Microsoft Dynamics 365, and Power BI. This integration streamlines workflows and enhances productivity.

Streamlined Email Management: Office 365 offers advanced email management features, such as archiving, eDiscovery, and retention policies. These tools help organizations comply with regulatory requirements and efficiently manage their email data.

Backup and Recovery: Office 365 includes backup and recovery options to protect against data loss. This feature is invaluable for safeguarding critical business data and ensuring business continuity.

Support and Maintenance: Microsoft offers robust support and maintenance for Office 365, reducing the burden on IT teams. This allows organizations to focus on their core business activities rather than managing email servers.

Methods to Migrate Mailbox from Windows Live Mail to Office 365

No single-step method can easily migrate Windows Live Mail to Office 365. There is a two-step process that needs to be followed:

  • Step 1: – Export Windows Live Mail Data for Office 365 Account
  • Step 2: – Import the Step 1 Resultant File into Office 365 User Account

Step 1: – Export Windows Live Mail Data for Office 365 Format

There are two ways to export WLM data for Office 365. You can use a manual method or professional software for this task. We have explained both methods below in detail:

Export Using Manual Methods:–

1st Method: Drag and Drop Method

  • 1. First, open your Outlook application.
  • 2. Then select File tab and then Add Account.
  • Export Windows Live Mail to Office 365 using Drag and Drop Method
  • 3. Here, provide your Office 365 sign-in credentials.
  • Step 3
  • 4. Now, click on the New Folder tab to create one.
  • Step 4
  • 5. Make a selection for the .eml files and drag them into the newly created folder.
  • Step 5
  • 6. And this how you can migrate Windows Live Mail to Office 365 as Windows Live Mail Creates EML files that saves single mail within it.
  • Step 6

2nd Method: Using Export and Import Method

  • 1. First of all, you need to open both the email clients, i.e., MS Outlook application and Windows Live Mail
  • 2. Now, on the main screen of Windows Live Mail, click on the File tab and choose the Export option; here, under the Export option, click on the Message option.
  • 3. Select Microsoft Exchange and click Next.
  • Export Windows Live Mail to Office 365 using Export and Import Method
  • 4. Now, the "Export Message" dialogue box appears on the screen.
  • 5. Here, click on the OK button.
  • Step 5
  • 6. Select the desired or all folders to proceed further and click on the OK button.
  • Step 6
  • 7. Now, the Export process gets a start.
  • Step 7
  • 8. Once the process is completed, you will receive a message – "Export Complete."
  • 9. You must click the "Finish" button to end the process.

Step 2: – Import the Step 1 Resultant File into Office 365 User Account

Users can execute this process in a manual way as well as by using the professional method. Both the tricks are explained here in brief:

Import Using Manual Method:–

If we talk about the manual solution, it has two types: Network Upload Method and Drive Shipping method. Below I’ve mentioned both methods

1. Network Upload method

2. Drive Shipping method

Due to their loopholes and technical processes, I don’t suggest any of them. Below I’ve mentioned some of the drawbacks the manual method came with.

Loopholes of the manual method to migrate Windows Live Mail to Office 365

While manually migrating Windows Live Mail to Office 365 is possible, there are several potential pitfalls and loopholes that can make the process challenging and error-prone. Here are some of the notable loopholes and issues associated with the manual migration method:

Complexity and Technical Expertise: Manual migration requires a good understanding of email protocols, server settings, and file formats. Non-technical users may find it difficult to navigate the complexities involved.

Data Loss and Incomplete Migration: Manual methods may not always transfer all emails, contacts, calendars, and other data accurately. There's a risk of data loss or incomplete migration, especially when dealing with large mailboxes.

Time-Consuming: Manual migration is a time-consuming process, especially when dealing with multiple user accounts or large volumes of data. It can disrupt productivity and strain IT resources.

Compatibility Issues: Compatibility problems may arise during manual migration, especially when dealing with different email clients and versions. This can lead to email formatting issues and data corruption.

Password and Authentication Challenges: Ensuring that the correct login credentials and authentication methods are used for each account can be challenging. Mistakes can lead to failed migrations.

Lack of Automation: Manual migration lacks automation, which means users and IT personnel need to perform repetitive tasks for each mailbox. This increases the likelihood of errors.

No Built-In Data Validation: Manual methods often lack data validation checks. This means there's no easy way to verify the integrity of the migrated data, increasing the risk of unnoticed errors.

Given these potential loopholes and challenges, many organizations and users opt for automated migration tools or services to migrate from Windows Live Mail to Office 365. These tools are designed to streamline the migration process, reduce the risk of data loss, and ensure a smoother transition.

Professional Tool: Regain EML to Office 365 Migration

Using this professional solution is quite easy. It can execute limitless migration without the risk of information loss. You are just required to download and install this Regain EML to Office 365 Migration software on your system, and it will easily import all emails into Office 365 account. Using this professional tool, one can easily import emails & attachments as well. It only takes a few steps to perform the migration process.


Features of the Regain EML to Office 365 migration tool:

  • Add EML Folder feature to migrate multiple EML files to Office 365 account in just a few clicks. Also, there is no EML file size limitation to perform the email migration.
  • Pause and Resume feature to pause and resume the migration process whenever needed.
  • Allows migrating selective EML files to Office365 account and Live MS Exchange Server platform with all mailbox items, including all email properties such as Contacts, Calendar, Attachments, Address Book, Tasks, Mails, etc.
  • Preserves original formatting, the structure of your EML files and folders hierarchy, and integrity.
  • Displays preview of all EML messages before migrating to an Office 365 account or MS Exchange Server and generates a complete report after completing email migration that can be saved for future reference.
  • Fully compatible with EML files generated from any email client, such as Windows Live Mail, Windows Mail, Thunderbird, Outlook, Outlook Express, etc.

Steps to Import Windows Live Mail to Office 365 Using Regain Software

  • 1. Download, install, and launch Regain EML to Office 365 Migration Software. The welcome screen of the software appears.
  • Windows Live Mail to Office 365 Migration using Regain Software
  • 2. Click Add EML Folder to add multiple EML files once for migration, or click Browse to select EML files for scanning.
  • Step 2
  • 3. The software starts scanning the added EML file(s).
  • Step 3
  • 4. After completing the scanning, the software displays a preview of all mailbox items.
  • 5. Click Office 365 and enter the login details of your Office 365 account.
  • 6. Click Connect to export EML files to Office 365 account.
  • Step 6

Final Conclusion:

To access and get the advantages of Office 365, you have to move from your default email client to your Office 365 account. And for that, you need to use an expert solution. Now, after discussing your query about the Windows Live Mail to Office 365 migration, how to migrate Windows Live Mail to Office 365 will resolve. We have explained the manual and the expert methods with a step-by-step guide to import emails from Windows Live Mail to an Office 365 user account. If you have any doubts or concerns, feel free to contact us. We always keep ourselves ahead to remove any doubt that comes to the minds of our users.

Frequently Asked Questions

Q1: Will my email attachments be preserved during the migration process?

Ans: Yes, when using professional migration tools like "Regain EML to Office 365 Migration," attachments are typically preserved, ensuring that you don't lose any important files associated with your emails.

Q2: How long does it take to complete a migration from Windows Live Mail to Office 365?

Ans: The time required for migration depends on factors such as the size of your mailbox, the speed of your internet connection, and the method used. Automated tools often offer faster migrations compared to manual methods.

Q3: Can I migrate multiple Windows Live Mail accounts to Office 365 simultaneously?

Ans: Yes, if you're using an automated migration tool, you can often migrate multiple accounts simultaneously, saving time and effort in larger migration projects.

Q4: Will my folder structure and hierarchy be preserved during the migration?

Ans: Professional migration tools are designed to preserve the original folder structure and hierarchy of your Windows Live Mail data, ensuring that your emails remain organized in Office 365.

Q5: Is it necessary to have technical expertise to use migration tools like "Regain EML to Office 365 Migration"?

Ans: While some technical knowledge can be helpful, user-friendly migration tools like "Regain EML to Office 365 Migration" often come with intuitive interfaces and step-by-step guides, making the process accessible to users with varying levels of technical expertise.

Q6: What should I do if I encounter errors during the migration process?

Ans: If you encounter errors or issues during the migration, you should refer to the documentation provided with your migration tool for troubleshooting steps. Additionally, you can seek support from the tool's customer service or technical support team.

Q7: Can I perform a test migration before migrating all my Windows Live Mail data to Office 365?

Ans: Many automated migration tools offer the option to perform a test or pilot migration to ensure that the process works smoothly before migrating all your data. This can be a good practice to minimize potential issues.

Q8: Is it possible to reverse the migration from Office 365 back to Windows Live Mail if needed?

Ans: While it's technically possible to revert from Office 365 to Windows Live Mail, it's a complex process and not recommended. It's essential to have backups and carefully consider the implications before attempting such a reversal.

Q9: How can I ensure data security during the migration process?

Ans: To ensure data security, it's crucial to use reputable migration tools, follow best practices, and consider encryption options if necessary. Additionally, always use secure and authorized methods to connect to your Office 365 account during migration.