Lionel Barrow’s short, furious tour of Microsoft 365 — republished and amplified by The Register — reads like a field report from an alien visitor trying to understand a human ritual: a thirty-something engineer raised on Gmail who steps into Exchange, Outlook, SharePoint, and Microsoft’s multi-headed group apparatus and emerges bewildered, amused, and alarmed.
The current debate is a familiar one: for many organizations, Microsoft Exchange and Outlook are non‑negotiable pillars of enterprise IT — a decades‑old, feature‑rich stack with deep ties to Active Directory and Windows Server. But the cloud era, the rise of Gmail and Google Workspace, and a new generation of users who learned work email on a web client have changed expectations. Gmail’s 2004 arrival as a fast, web‑first mail client helped shift user tastes toward simplicity and reliable web UX, and Google’s later acquisitions (Writely in 2006, spreadsheet tech from 2Web in 2006) seeded a powerful, simple alternative to heavyweight groupware.
Over the same period Microsoft migrated enormous amounts of legacy, enterprise‑grade functionality into the cloud as Microsoft 365, while also trying to preserve backward compatibility for customers running on‑premises Exchange, Windows Server, and Active Directory. The tradeoff: an ecosystem that now mixes decades of legacy behaviors, a sprawling set of web apps, and continuing attempts to fold everything into a unified Microsoft 365 experience. Microsoft’s official lifecycle calendar underscores the urgency for some organizations to move: multiple legacy products (including Office 2016/2019 and Exchange Server 2016/2019) reached—and in many cases reach—end of support on October 14, 2025, a hard pivot that Microsoft uses to encourage cloud migration.
Microsoft could choose a radical strategy — prune the product family to a small, opinionated core and offer optional “power packs” — but that risks alienating an installed base. Conversely, retaining all features keeps the conversion funnel open for enterprise sales but preserves complexity.
There is a middle path: better defaults, clearer surface area boundaries, and explicit “simplicity” product lines (lightweight Outlook/Office experiences with fewer options for SMBs) could deliver the UX Barrow wants without abandoning enterprise customers. Some Microsoft moves (e.g., MinWin explorations in the Windows 7 era) show the company can build small cores when it commits to doing so.
Practical takeaways for IT leaders:
Source: theregister.com 'Don't even consider' Microsoft? Gosh
Background / Overview
The current debate is a familiar one: for many organizations, Microsoft Exchange and Outlook are non‑negotiable pillars of enterprise IT — a decades‑old, feature‑rich stack with deep ties to Active Directory and Windows Server. But the cloud era, the rise of Gmail and Google Workspace, and a new generation of users who learned work email on a web client have changed expectations. Gmail’s 2004 arrival as a fast, web‑first mail client helped shift user tastes toward simplicity and reliable web UX, and Google’s later acquisitions (Writely in 2006, spreadsheet tech from 2Web in 2006) seeded a powerful, simple alternative to heavyweight groupware. Over the same period Microsoft migrated enormous amounts of legacy, enterprise‑grade functionality into the cloud as Microsoft 365, while also trying to preserve backward compatibility for customers running on‑premises Exchange, Windows Server, and Active Directory. The tradeoff: an ecosystem that now mixes decades of legacy behaviors, a sprawling set of web apps, and continuing attempts to fold everything into a unified Microsoft 365 experience. Microsoft’s official lifecycle calendar underscores the urgency for some organizations to move: multiple legacy products (including Office 2016/2019 and Exchange Server 2016/2019) reached—and in many cases reach—end of support on October 14, 2025, a hard pivot that Microsoft uses to encourage cloud migration.
What Barrow actually experienced: the practical complaints
Lionel Barrow’s post catalogs a set of concrete, surface‑level irritations that stack into a broader pattern of inconsistency and cognitive friction:- Outlook and Calendars: threaded meeting notifications, opaque update channels, and behaviors like declined meetings disappearing from calendars by default. Those are not mere stylistic gripes — they have operational consequences for invitations, recurring meeting updates, and event tracking. Microsoft now offers a Save declined events setting in the new Outlook family to preserve declined events, but it’s off by default and historically the platform’s behavior was indeed to remove declined entries. That nuance matters: defaults shape user expectations.
- SharePoint and OneDrive: confusion over two seemingly distinct “apps” that actually share a storage backend. In Microsoft 365 the content services behind file storage are powered by SharePoint; OneDrive for Business is the personal document surface and editing layer that sits on top of the same SharePoint content platform. That architecture produces inconsistent UIs and different search scopes depending on which web surface a user is on. What looks like duplication is really a split between content services and user experience surfaces.
- Groups, identities, and permissions: a bewildering array of constructs — Outlook Groups, Distribution Lists, Exchange profile groups, and Microsoft Entra (Azure AD) groups — each with distinct semantics, admin surfaces, and integration points. Barrow’s discovery that Microsoft 365 Groups cannot be nested is a textbook example of a small technical constraint becoming a large organisational headache; nested group behavior is limited for Microsoft 365 Groups, and Azure AD explicitly documents supported and unsupported nested‑group scenarios.
Why this matters to administrators and decision‑makers
Barrow’s account is not just a rant; it highlights three operational truths that matter when you build or run corporate IT.- Defaults drive behavior. Many organizations never change defaults. If an environment defaults to removing declined meetings, or if the default search box operates differently from one web surface to another, users learn unexpected behaviors and trust erodes over time. Microsoft has added features to mitigate some of these defaults — but the fixes are often opt‑in and tenant‑level.
- Backward compatibility creates architectural drag. Microsoft’s need to support millions of installed servers, admins, and edge cases makes it reluctant to remove or radically simplify “power” features. Many of those features are still mission‑critical for a subset of enterprise customers. That’s both a strength and a constraint: maintaining power features preserves deep enterprise capabilities, but also keeps the complexity bar high.
- Surface fragmentation increases support costs. Multiple web apps that look similar but search different data stores, or group models that overlap with inconsistent semantics, create helpdesk tickets and latent failure modes. In practice, that increases operational overhead and the chance of missed calendar updates, failed file permissions, or missed communications.
Technical reality checks (what’s factual, what’s changed)
A few of Barrow’s observations read like “this was broken forever” but deserve technical context and verification.- Office and Exchange end‑of‑support: Microsoft lists Office 2016/2019 and Exchange Server 2016/2019 as reaching end of support on October 14, 2025. That date is real and is guiding many migration plans; Microsoft’s lifecycle pages and the Exchange Team blog reinforce the same deadlines and migration guidance. For organizations using on‑prem Exchange, this deadline compresses migration windows and raises both compliance and security concerns.
- OneDrive is backed by SharePoint content services: this is accurate for OneDrive for Business — OneDrive acts as a personal front end; SharePoint provides the company‑wide content infrastructure, and many OneDrive URLs point to tenant‑my.sharepoint.com. That architecture explains behavioral oddities Barrow observed (e.g., comments appearing from a “SharePoint Online” identity).
- The “new Outlook” limitations: Microsoft’s newer web‑language Outlook clients intentionally target Exchange Online and a defined set of account types; on‑premises Exchange accounts and certain license SKUs are not fully supported in the new Outlook as of mid‑2025. That explains why some users see degraded capabilities or are unable to add local Exchange mailboxes to the new client. Microsoft documents supported account types and lists on‑prem Exchange as unsupported in several scenarios.
- Declined meetings: by default, many classic Outlook clients historically removed declined meetings from the calendar; Microsoft introduced a cross‑client setting to preserve declined events in newer client versions, but it must be enabled. So Barrow’s surprise at the behavior was understandable and remains relevant until tenants update defaults and user training.
- Microsoft 365 Groups and nesting: nested groups in Azure AD are supported only for a subset of scenarios, and Microsoft 365 Groups are specifically listed among unsupported nested scenarios for some group operations. That limitation is often surprising for admins who expect traditional Active Directory nesting semantics.
Strengths of Microsoft’s approach (why many customers stay)
It’s easy to focus on frustration; it’s also important to recall why Microsoft’s stack endures.- Feature depth and integration. Exchange, Outlook, SharePoint, Teams, and Entra/Active Directory form a tightly integrated stack that supports fine‑grained security controls, enterprise governance, and compliance features many regulated industries require. Active Directory’s arrival in Windows 2000 set the stage for centralized identity and policy control that enterprises still rely on.
- Backward compatibility and enterprise tooling. Many organizations rely on features and workflows that have been battle‑tested for 15+ years. Microsoft’s tendency to preserve those capabilities reduces migration risk for mission‑critical apps.
- Managed security posture at scale. For many defenders, Exchange Online and Microsoft 365 provide a better managed security baseline (DDoS, anti‑spam, automated patching) than a small IT team could deliver on‑premises. That’s why Microsoft is pressing its cloud model — a practical security and operational argument that resonates for many enterprises.
Risks and costs: usability, lock‑in, and outages
Barrow’s takeaway — “I was surprised at how badly thought out this all seems” — maps cleanly to three institutional risks.- User experience fragmentation. Multiple surfaces with different behaviors increase cognitive load. The younger workforce raised on Gmail expects simple, consistent behavior; when they encounter Exchange’s idiosyncrasies, it feels like needless friction.
- Vendor lock‑in. Deep integration across Entra/Exchange/SharePoint/Teams raises switching costs. Even where alternatives exist, moving mail, calendars, files, and identity bindings from one platform to another is operationally expensive.
- Cloud outage dependency. Microsoft 365 outages or configuration errors can cascade across email, calendaring, file access, and Teams collaboration. Community threads and incident reporting show the real cost of those outages in lost productivity and emergency IT work. Those are not theoretical risks; they recur and create incentives to maintain heterogeneity (e.g., keep a secondary email service or local archive) — at the cost of complexity.
Alternatives and realistic escape routes
Barrow’s implicit question is: should organizations “just use Gmail”? The pragmatic answers are mixed.- For many small and medium teams, Google Workspace does deliver the simpler, more predictable UX Barrow praises. Gmail + Google Drive + Docs + Calendar cover most day‑to‑day workflows with far fewer admin surfaces, and Google’s product acquisitions in 2006 helped create that suite. That simplicity is the reason many companies choose Google as the baseline and continue to onboard employees without heavy training.
- For enterprises with strict compliance or legacy application dependencies, Microsoft remains the pragmatic choice because of AD/Group Policy, Exchange’s calendaring primitives, and deep third‑party integrations.
- The open‑source and hosted groupware ecosystem has persisted in niches: Open‑Xchange, Scalix, Zimbra, and others offer alternatives. Open‑Xchange claims hundreds of millions of users at scale among telcos and hosting providers and provides an example of a viable alternative for service providers and some enterprises. But these options rarely put a dent in Microsoft’s market share in large enterprises because the ecosystem of integrations and third‑party support is smaller.
- Inventory and dependency mapping: list apps, mailboxes, archives, and automations tied to Exchange/AD/SharePoint.
- Identify the “must‑keep” features: shared mailboxes, delegation, archival compliance, eDiscovery, legal hold, etc.
- Pilot with non‑critical groups: pilot Google Workspace or Open‑Xchange for a single team, learn the edge cases.
- Run a hybrid migration or co‑existence period: synch mail via secure connectors, and stage cutoff windows.
- Train users and change defaults: most friction comes from defaults and muscle memory — invest in user training.
Product management reflections: complexity vs. “Just Barely Good Enough”
Barrow (and our own experience) identify a product‑management dilemma. Microsoft’s enterprise features are valuable to large, security‑sensitive customers. But those same features create cognitive overhead for a new generation of workers. Google’s competitive advantage was never a perfect feature match; it was “good enough” plus simplicity and consistency.Microsoft could choose a radical strategy — prune the product family to a small, opinionated core and offer optional “power packs” — but that risks alienating an installed base. Conversely, retaining all features keeps the conversion funnel open for enterprise sales but preserves complexity.
There is a middle path: better defaults, clearer surface area boundaries, and explicit “simplicity” product lines (lightweight Outlook/Office experiences with fewer options for SMBs) could deliver the UX Barrow wants without abandoning enterprise customers. Some Microsoft moves (e.g., MinWin explorations in the Windows 7 era) show the company can build small cores when it commits to doing so.
Conclusion: what IT leaders should take away
Lionel Barrow’s dispatch is a timely reminder that engineering excellence is not just technical depth; it’s also clarity of experience. Microsoft’s stack is extraordinary in capability and staggering in its accumulated baggage. That baggage matters — for users who expect simple, predictable behaviour, and for organisations that must weigh uptime, compliance, and cost.Practical takeaways for IT leaders:
- Audit defaults and tenant settings now. Small toggles (for example, preserving declined events, or choosing which Outlook client you standardize on) cut straight to the daily pain users feel.
- Treat migration timelines as project risks, not calendar warnings: end‑of‑support dates are hard deadlines for security posture planning.
- Consider heterogeneity as a resilience strategy: keep fallbacks for calendaring and email continuity if you run critical operations that cannot tolerate a single‑vendor outage. Community incident reports underline how costly outages can be in real time.
- Finally, product teams should take the Barrow critique as user research: there is a generational shift in expectations. Simplification, smarter defaults, and clearer product boundaries are product decisions that could reduce support load while widening adoption.
Source: theregister.com 'Don't even consider' Microsoft? Gosh