If you’re transitioning to the latest version of Microsoft Outlook or need to compare it with the classic version, running both side by side can streamline your workflow. This guide covers how to set up and use both Outlook versions simultaneously, ideal for IT administrators, power users, and anyone seeking a smooth transition or comparison experience.
1. Use Outlook Desktop App with Legacy Mode
Microsoft Outlook allows users to run the latest version while still accessing the classic interface through legacy modes or add-ins. For example, Outlook 365 can be configured to open in a minimized or simplified mode, enabling you to compare features or maintain familiarity with older workflows without switching programs. This approach is especially useful for organizations transitioning to new software but wanting to preserve operational continuity.
2. Install Both Outlook Versions on the Same Machine
You can install the new Outlook (part of Microsoft 365) alongside the classic Outlook 2016 or 2019 on the same Windows PC. To avoid conflicts, ensure that the installations are in separate directories and that your email accounts are configured correctly in each. Running both allows you to test new features while maintaining the familiar interface, making it ideal for IT testing or user training.
3. Use Outlook Web Access (OWA) and Desktop Together
Microsoft Outlook’s web version (OWA) offers a nearly identical experience to the desktop app. You can open OWA in a browser window while running the desktop Outlook, enabling side-by-side comparison of email management, calendar features, and settings. This method is quick to set up and doesn’t require installing multiple applications, making it perfect for quick workflows or remote work scenarios.
4. Leverage Multiple Monitors for Simultaneous Viewing
If your workstation has multiple monitors, you can open the new Outlook on one screen and the classic version on another. This setup allows you to drag and arrange windows for easy comparison or to copy information between versions. It’s especially useful for data entry, email triage, or when training colleagues on new features while referencing the classic interface.
5. Use Virtual Machines or Sandbox Environments
Running different Outlook versions in virtual machines (using Hyper-V, VMware, or VirtualBox) provides an isolated environment for testing or comparison. You can set up one VM with the classic Outlook and another with the new version, switching between them without risking conflicts. This method is ideal for enterprise IT teams and developers who need to verify compatibility or perform extensive testing.
6. Enable Compatibility Mode
For older Outlook versions that encounter issues on newer Windows builds, compatibility mode can help run classic Outlook smoothly alongside the latest version. Right-click the Outlook shortcut, select Properties, then Compatibility, and choose an older Windows version. This allows continued use of the classic interface while still accessing the new Outlook features in parallel.
7. Use Outlook Add-ins to Bridge Features
Some third-party add-ins enable you to synchronize or view features from both Outlook versions simultaneously. For example, add-ins like MAPILab’s Add-in for Outlook allow extended functionality, such as unified inboxes or shared calendars, bridging the gap between different Outlook environments. This is particularly useful for users who need to manage multiple accounts or migrate gradually.
8. Configure Multiple Profiles in Outlook
Outlook supports multiple profiles, each with its own account settings and interface preferences. By creating separate profiles—one for the classic version and another for the new Outlook—you can switch between them easily, running each side by side. This setup is beneficial for testing new features, troubleshooting, or managing different work and personal accounts separately.
9. Use Remote Desktop or Cloud-Based Access
Accessing Outlook through remote desktop tools like Microsoft Remote Desktop or Windows Virtual Desktop allows you to run different versions in separate environments. For example, you can connect to a virtual machine with the classic Outlook while your local machine runs the new version. This method is ideal for enterprise environments with strict software deployment policies.
10. Synchronize Settings and Data for Consistency
When running Outlook side by side, ensure your email accounts and data are synchronized across both versions. Use Exchange or Outlook Data Files (.pst) to keep emails, contacts, and calendars consistent. This ensures a seamless experience, whether you’re comparing interfaces or transitioning between versions, and reduces the risk of data discrepancies.
How to Choose
Choosing between the new and classic Outlook depends on your specific needs. Consider factors like interface familiarity, feature requirements, compatibility with existing systems, and your comfort level with new technology. For ongoing productivity, running both versions simultaneously can provide a safety net, allowing you to adapt gradually while maintaining access to essential features in the classic interface.
Frequently Asked Questions
Can I run Outlook 2016 and Outlook 365 on the same computer?
Yes, but it’s recommended to install them in separate directories and profiles to prevent conflicts. Running both helps transition smoothly from older to newer versions.
Will running two Outlook versions cause data conflicts?
Generally no if your accounts are configured correctly and data is stored on the server (like Exchange). Always back up data before testing multiple versions.
Is it possible to view both Outlook versions on one screen?
Yes, using multiple monitors or windowed modes, you can open both versions side by side for comparison or multitasking.
Are there risks in running Outlook in compatibility mode?
Compatibility mode can sometimes cause performance issues or minor glitches, but it’s often necessary for older versions on newer OSes. Use it judiciously.
How can I ensure my data stays synchronized across versions?
Use Exchange accounts or export/import .pst files regularly to keep emails, contacts, and calendars consistent across Outlook versions.
Is running Outlook in a virtual machine complicated?
It requires some technical setup, including VM software and configuring Outlook inside the VM, but it offers complete isolation for testing or comparison.
Final Thoughts
Running new Outlook and classic Outlook side by side offers a flexible approach to managing email and calendar workflows during transitions or testing phases. By leveraging multiple profiles, virtual environments, or multi-monitor setups, users can enjoy the best of both worlds—access to cutting-edge features while retaining familiarity. Careful configuration and regular data synchronization ensure a smooth experience, making it easier than ever to adapt to new software or maintain legacy workflows without disruption.
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