Microsoft’s ongoing campaign to shift users from the venerable classic Outlook desktop client toward its new Outlook for Windows app underscores both the company’s commitment to modernity and the challenges inherent in remaking a legacy productivity tool. The June 2025 refresh of the new Outlook delivers some high-profile enhancements—most notably AI-powered Copilot integration, broader offline capabilities, and incremental functional updates. Still, for many power users, IT admins, and even some everyday emailers, the new app remains an uneven replacement for the classic client, highlighting the complex tug-of-war between innovation and user trust in the Microsoft ecosystem.
The most headline-grabbing change is the official rollout of Microsoft’s Copilot AI within the new Outlook for Windows. With Copilot, users can summon generative AI assistance across all connected email accounts—including not only Microsoft’s own Outlook.com, Hotmail.com, Live.com, and MSN.com, but also popular third-party platforms such as Gmail, Yahoo, and iCloud. This marks a significant expansion of Copilot’s reach, pushing the new AI to a broader user base than ever before.
To take advantage of Copilot in Outlook, users must either hold a Copilot Pro subscription or possess available Copilot AI credits via a Microsoft 365 Personal or Family plan. Once enabled, Copilot appears as an icon in the app’s top toolbar, ready to aid with email drafting, text rewriting, grammatical improvements, tone adjustments, and more. For example, users can task Copilot with composing a draft email to request a raise or to polish an existing note for clarity and professionalism. There’s also a coaching option, which offers message-improving suggestions reminiscent of writing-assistant platforms like Grammarly or Google’s Smart Compose.
Compared to similar AI integrations in Google Workspace and competitor email clients, Copilot stands out for its breadth and ability to work across disparate accounts in one place—a clear value proposition for users managing multiple inboxes. However, accessibility is gated behind a paid subscription or existing Microsoft 365 membership, possibly alienating a segment of users who might expect core generative AI features as part of the standard package.
Further, while Copilot’s AI can be easily disabled by toggling a Switch in Outlook’s Copilot settings, questions remain about user data privacy and how prompts or email contents are processed and retained by Microsoft’s cloud. Although Microsoft claims to follow strict privacy and security protocols, users handling sensitive business communications may wish to carefully review their organization’s data governance policies before embracing AI assistance at scale.
These updates represent important steps towards feature parity with the classic Outlook desktop client, which has always boasted deep offline functionality and seamless local storage through its PST file format. Still, the improvements fall somewhat short: the new Outlook’s offline experience remains less extensive compared to the classic client, particularly for those managing massive mail archives, custom rules, or intricate folder structures.
The increased 30-day offline window is a welcome change for travelers or staff in low-connectivity environments. But for enterprise use cases, several limitations persist:
Additionally, the app now enables users to move emails between different personal accounts with less friction and tag shared folders as favorites. These incremental improvements help mitigate some of the pain points for users juggling complex mailbox environments, though the absence of deep enterprise controls, advanced compliance features, or full shared mailbox parity may frustrate larger organizations.
However, these improvements appear to come at the cost of advanced functionality. The new Outlook’s design (largely web-based, sometimes described as an Electron wrapper) may limit its extensibility, especially for users accustomed to building custom workflows with VBA macros. As of June 2025, the new Outlook does not support VBA at all—a significant loss for power users, businesses, or anyone relying on automation to process complex mailbox routines.
Other persistent limitations compared to the classic client include:
Microsoft, for its part, frames the transition as a necessary modernization, pointing to security improvements, faster feature rollouts, and better consistency across desktop and web. But for many, the specter of forced migration—particularly if core features aren’t ready—breeds anxiety and resentment. The debate mirrors Microsoft’s previous pushes (think Windows 8, the Windows 11 hardware requirements, or the compulsory transition from Internet Explorer to Edge), where well-intentioned innovation clashed with the inertia of a vast, diverse user base.
Thus far, Microsoft has not set a firm sunset date for the classic Outlook desktop client, and company representatives have at times suggested that both apps will coexist for the foreseeable future. Nevertheless, repeated nudges within Windows, Office, and the Microsoft 365 ecosystem signal the company’s keen interest in consolidating most users on the new, cloud-centric client.
But in aiming for a broader, more accessible audience, the new Outlook can feel oversimplified. The feature gaps—laid bare when compared with the classic client—make it difficult to recommend to anyone with advanced needs, large mail archives, complex calendar obligations, or reliance on powerful scripting and macro tools.
Organizations bound by strict compliance or data sovereignty rules may also be reluctant to embrace a more cloud-reliant app, especially amid evolving worldwide privacy regulations. While Microsoft works continually to enhance the enterprise chops of new Outlook, these limitations will likely persist through several more update cycles.
This dual-track approach would mirror strategies taken by other software vendors (such as Adobe with Acrobat and Acrobat Reader, or Apple with basic and “Pro” versions of several apps). It acknowledges the reality that migration isn’t just about bringing old data forward, but also embracing diverse workstyles, security needs, and regulatory contexts.
Ultimately, the biggest risk facing Microsoft isn’t technological stagnation, but the alienation of its most loyal and productive users—those who built their business routines (and IT investments) around the rich flexibility of the classic Outlook.
For now, users have a choice. But the pace of recent updates and Microsoft’s consolidation rhetoric suggest that choice may soon be curtailed. For enterprise IT departments, compliance managers, and power users, now is the time to evaluate the evolving feature set of the new Outlook—and to make their voices heard before migration moves from “suggestion” to “requirement.”
In the long run, the best outcome for users and the company alike may be a layered approach: let innovation thrive in the new Outlook, but keep the classic client alive and evolving for those who depend on its unmatched flexibility. Microsoft’s challenge is to prove that the future can be both exciting and accommodating, not just for the masses, but for the experts who’ve kept Outlook—and Microsoft—at the pinnacle of business productivity for decades.
Until the new Outlook reaches full parity with its predecessor, Microsoft should resist the temptation to rush users, continuing instead to support and improve both versions. Only then can the company ensure that innovation doesn’t come at the cost of alienating its most experienced and demanding customers—who, more than ever, expect software that combines both intelligence and trustworthiness in the modern workplace.
Source: ZDNET The new Outlook for Windows adds Copilot and other perks, but I still prefer the classic version
Copilot AI Takes Center Stage
The most headline-grabbing change is the official rollout of Microsoft’s Copilot AI within the new Outlook for Windows. With Copilot, users can summon generative AI assistance across all connected email accounts—including not only Microsoft’s own Outlook.com, Hotmail.com, Live.com, and MSN.com, but also popular third-party platforms such as Gmail, Yahoo, and iCloud. This marks a significant expansion of Copilot’s reach, pushing the new AI to a broader user base than ever before.To take advantage of Copilot in Outlook, users must either hold a Copilot Pro subscription or possess available Copilot AI credits via a Microsoft 365 Personal or Family plan. Once enabled, Copilot appears as an icon in the app’s top toolbar, ready to aid with email drafting, text rewriting, grammatical improvements, tone adjustments, and more. For example, users can task Copilot with composing a draft email to request a raise or to polish an existing note for clarity and professionalism. There’s also a coaching option, which offers message-improving suggestions reminiscent of writing-assistant platforms like Grammarly or Google’s Smart Compose.
Compared to similar AI integrations in Google Workspace and competitor email clients, Copilot stands out for its breadth and ability to work across disparate accounts in one place—a clear value proposition for users managing multiple inboxes. However, accessibility is gated behind a paid subscription or existing Microsoft 365 membership, possibly alienating a segment of users who might expect core generative AI features as part of the standard package.
Further, while Copilot’s AI can be easily disabled by toggling a Switch in Outlook’s Copilot settings, questions remain about user data privacy and how prompts or email contents are processed and retained by Microsoft’s cloud. Although Microsoft claims to follow strict privacy and security protocols, users handling sensitive business communications may wish to carefully review their organization’s data governance policies before embracing AI assistance at scale.
Meaningful, If Incremental, Offline Improvements
Alongside Copilot, the new Outlook app has gained more robust offline capabilities. It now supports storing up to 30 days of emails locally (up from the previous seven), making it a more practical option than before for users who spend significant time away from stable internet connections. Search folders—a productivity cornerstone for power users—are now accessible offline, and users gain the ability to cancel a sent email even when working offline.These updates represent important steps towards feature parity with the classic Outlook desktop client, which has always boasted deep offline functionality and seamless local storage through its PST file format. Still, the improvements fall somewhat short: the new Outlook’s offline experience remains less extensive compared to the classic client, particularly for those managing massive mail archives, custom rules, or intricate folder structures.
The increased 30-day offline window is a welcome change for travelers or staff in low-connectivity environments. But for enterprise use cases, several limitations persist:
- Not all account types are supported offline.
- Power features such as custom filters, rules, and macros are still not available when offline.
- Synchronization delays and data consistency may become problematic for those handling sensitive or time-critical information.
PST and Account Management Catch Up (Slowly)
One of the classic Outlook client’s enduring advantages has been its detailed support for PST files, Microsoft’s personal storage table format for keeping local copies of emails and calendar data. With this round of updates, the new Outlook app now lets users reply to and forward emails stored within PSTs, expanding its utility for those with significant local archives. Microsoft promises further improvements to PST support in future releases—a wise move, given the sheer number of users who rely on PSTs for archiving, migration, or redundancy.Additionally, the app now enables users to move emails between different personal accounts with less friction and tag shared folders as favorites. These incremental improvements help mitigate some of the pain points for users juggling complex mailbox environments, though the absence of deep enterprise controls, advanced compliance features, or full shared mailbox parity may frustrate larger organizations.
Slick, Fast, and Lightweight—But Is That Enough?
Microsoft touts the new Outlook for Windows as a fast, visually pleasing, and lightweight alternative to the classic client. For many, especially casual or consumer users, these attributes represent a real advantage: quicker launch times, clean navigation, and an interface that aligns with modern Windows design language.However, these improvements appear to come at the cost of advanced functionality. The new Outlook’s design (largely web-based, sometimes described as an Electron wrapper) may limit its extensibility, especially for users accustomed to building custom workflows with VBA macros. As of June 2025, the new Outlook does not support VBA at all—a significant loss for power users, businesses, or anyone relying on automation to process complex mailbox routines.
Other persistent limitations compared to the classic client include:
- No or limited support for certain types of enterprise accounts (such as on-premises Exchange, legacy SMTP, or IMAP accounts with advanced settings).
- Incomplete parity for calendar, contact management, and public folder scenarios.
- Reduced ability to manipulate or migrate large mail archives.
- Fewer integration points for third-party add-ins, especially those tailored for enterprise compliance.
Strong-Arm Tactics and User Backlash
Beyond technical pros and cons, Microsoft’s approach to pushing the new Outlook has sparked significant user criticism. Some see the company’s tactics as “strong-arm,” with the new app gradually positioned to replace older applications such as Windows Mail & Calendar (a favorite among users seeking simplicity) and, eventually, even the classic Outlook client bundled with Microsoft 365/Office subscriptions.Microsoft, for its part, frames the transition as a necessary modernization, pointing to security improvements, faster feature rollouts, and better consistency across desktop and web. But for many, the specter of forced migration—particularly if core features aren’t ready—breeds anxiety and resentment. The debate mirrors Microsoft’s previous pushes (think Windows 8, the Windows 11 hardware requirements, or the compulsory transition from Internet Explorer to Edge), where well-intentioned innovation clashed with the inertia of a vast, diverse user base.
Thus far, Microsoft has not set a firm sunset date for the classic Outlook desktop client, and company representatives have at times suggested that both apps will coexist for the foreseeable future. Nevertheless, repeated nudges within Windows, Office, and the Microsoft 365 ecosystem signal the company’s keen interest in consolidating most users on the new, cloud-centric client.
Who Is the New Outlook For?
The new Outlook’s strengths are clear: it delivers a polished, fast experience for typical home and small business users, offers tight integration with other Microsoft apps, and now brings AI-powered messaging capabilities to a mass audience. For those managing a basic set of email accounts or seeking a modern UI without the baggage of legacy features, it may already be superior to both Windows Mail and the classic Outlook.But in aiming for a broader, more accessible audience, the new Outlook can feel oversimplified. The feature gaps—laid bare when compared with the classic client—make it difficult to recommend to anyone with advanced needs, large mail archives, complex calendar obligations, or reliance on powerful scripting and macro tools.
Organizations bound by strict compliance or data sovereignty rules may also be reluctant to embrace a more cloud-reliant app, especially amid evolving worldwide privacy regulations. While Microsoft works continually to enhance the enterprise chops of new Outlook, these limitations will likely persist through several more update cycles.
The Case for Choice: Parallel Development
Rather than forcing users into a one-size-fits-all future, many observers argue that Microsoft should continue developing both Outlook clients in parallel. By targeting the new Outlook at consumers and basic business needs, while maintaining the classic client for advanced use cases and enterprises, Microsoft could gradually close the gaps at a user-friendly pace—even as it iterates on modern design and cloud-powered features.This dual-track approach would mirror strategies taken by other software vendors (such as Adobe with Acrobat and Acrobat Reader, or Apple with basic and “Pro” versions of several apps). It acknowledges the reality that migration isn’t just about bringing old data forward, but also embracing diverse workstyles, security needs, and regulatory contexts.
Ultimately, the biggest risk facing Microsoft isn’t technological stagnation, but the alienation of its most loyal and productive users—those who built their business routines (and IT investments) around the rich flexibility of the classic Outlook.
Looking Ahead: A Delicate Balancing Act
Microsoft finds itself at a crossroads: on one side, the allure of AI-driven productivity, streamlined experiences, and cross-platform consistency; on the other, the hard-won trust of millions who depend on Outlook’s legacy strengths. The latest round of new Outlook updates—a slate that includes Copilot integration, improved offline features, and incremental PST support—represents meaningful progress. Yet, these advances only underscore how much further the new app must go before it can truly replace the classic Outlook for all user segments.For now, users have a choice. But the pace of recent updates and Microsoft’s consolidation rhetoric suggest that choice may soon be curtailed. For enterprise IT departments, compliance managers, and power users, now is the time to evaluate the evolving feature set of the new Outlook—and to make their voices heard before migration moves from “suggestion” to “requirement.”
In the long run, the best outcome for users and the company alike may be a layered approach: let innovation thrive in the new Outlook, but keep the classic client alive and evolving for those who depend on its unmatched flexibility. Microsoft’s challenge is to prove that the future can be both exciting and accommodating, not just for the masses, but for the experts who’ve kept Outlook—and Microsoft—at the pinnacle of business productivity for decades.
Comparison Table: Classic vs New Outlook (As of June 2025)
| Feature | Classic Outlook Desktop | New Outlook for Windows |
|---|---|---|
| Copilot AI Support | No | Yes (with subscription) |
| PST File Full Support | Yes | Partial, improving |
| Offline Email Storage | Unlimited | Up to 30 days |
| VBA Macro/AUTOMATION | Yes | No |
| Multiple Account Types | Broad | Many, but not all |
| Enterprise Compliance | Advanced | Evolving, some gaps |
| Third-Party Add-ins | Mature Ecosystem | Limited, expanding |
| Speed/Lightweight | Can be slow/bloated | Fast and lightweight |
| UI Modernization | Legacy/Classic | Modern Windows style |
| AI Drafting/Rewrite | No | Yes (with Copilot) |
| Search Folders Offline | Yes | Yes (now available) |
| Shared Mailbox Support | Complete | Partial |
| User Customization | Extensive | Limited |
Final Thoughts
Moving forward, Microsoft must navigate a delicate balance between progress and continuity. While Copilot, offline improvements, and increased PST support are clear upgrades, the enduring importance of depth and flexibility in an email client cannot be overstated—especially among the enterprise and power-user audiences that have long made Outlook indispensable.Until the new Outlook reaches full parity with its predecessor, Microsoft should resist the temptation to rush users, continuing instead to support and improve both versions. Only then can the company ensure that innovation doesn’t come at the cost of alienating its most experienced and demanding customers—who, more than ever, expect software that combines both intelligence and trustworthiness in the modern workplace.
Source: ZDNET The new Outlook for Windows adds Copilot and other perks, but I still prefer the classic version
