Microsoft is undermining Outlook’s role as the backbone of professional communication by forcing heavy users through the Office 365 funnel. Add-ins like MailMaestro, Copilot, and Boomerang are locked away, the product line is fragmented across multiple Outlook clients, and serious multi-inbox management is ignored. Rivals such as Spark, Canary, Mailbird, Superhuman, and even newer “hip” tools like Hey! show more imagination. The lost promise of Google Wave reminds us that integration, not fragmentation, is the real opportunity, while Microsoft’s current short-sighted strategy leaves it weaker than ever. Email remains the killer app of the internet, so why, after all this time, is it still so shite?

For over two decades, Microsoft Outlook has been the go-to email client for serious email users. It became the workhorse of professionals juggling multiple accounts, projects, and time zones. Outlook’s greatest strength was its flexibility: connect Exchange, POP, IMAP, Gmail, Yahoo, your ISP account, even the odd server running in a cupboard, and Outlook would cheerfully keep them all in one place.

Today, that vision is under threat. Microsoft has quietly forced everything through the Office 365 funnel. If you want new features, add-ins, or AI assistance, you’re told to abandon the version of Outlook you actually use and install the “right” Microsoft 365 client. The result is a fractured experience that actively punishes heavy email users.

The Problem with Microsoft’s Strategy

1. Add-ins are locked behind 365
   • Outlook’s productivity ecosystem — MailMaestro, Copilot, Boomerang — now lives exclusively in the Microsoft 365 AppSource store.
   • Running Outlook 2019, 2021, or even a perpetual licence that comes bundled with Office? You’re excluded, even if you’re paying for a Microsoft 365 subscription.
2. The “New Outlook” confusion
   • Windows 11 pushes a “new Outlook” client that is essentially the web app in a wrapper. It lacks the power tools and reliability of the classic client. Add-ins don’t all work there either.
   • Result: three different Outlooks (classic 365, perpetual 2019/21, new preview), none of which offer a coherent AI and add-in story.
3. Industrial, aka “heavy”, email use breaks the model
   • Microsoft has optimised Outlook for the “average” corporate user — one Exchange mailbox, some Teams integration, and a light sprinkling of AI.
   • For those managing dozens of inboxes, dealing with high-volume correspondence, or needing deep filing and automation, the strategy falls apart. AI tools are surface-level; the core pain of multi-account management remains untouched.

Take MailMaestro as an example. It’s a thoughtful AI assistant that can summarise threads, draft replies, and help prioritise. It’s exactly the sort of innovation heavy email users are desperate for. But unless you’re running the precise flavour of Outlook that Microsoft dictates, you can’t even install it. The barrier isn’t technology; it’s Microsoft’s lock-in.

Rivals Are Eating Microsoft’s Lunch

While Microsoft is busy corralling users into 365 subscriptions, competitors are quietly solving real problems:

• Spark Mail → Designed for multiple accounts, it gives you a true unified inbox, team collaboration, and an AI assistant that sorts, summarises, and drafts. It works across Mac, Windows, iOS, and Android — with none of Outlook’s licensing complexity.
• Canary Mail → Privacy-first, with an AI “Copilot” that prioritises your inbox, suggests replies, and unifies mail from dozens of accounts. It handles Gmail, iCloud, Exchange, IMAP, and Outlook accounts seamlessly.
• Mailbird → A Windows client with ChatGPT integration, making AI assistance feel natural. It doubles as a hub for messaging apps like WhatsApp and Slack — something Outlook has never cracked.
• Superhuman → Pricey, but it has nailed the “speed plus AI” experience. Summaries, follow-ups, and reminders are baked into a lightning-fast client that many ex-Outlook power users now swear by.
• The New “Hip” Alternatives
  While Microsoft clings to its legacy stack, newer platforms like Hey! (from Basecamp) have reimagined email as a controlled environment. They push features like screening senders, feed-style views, and focus modes that break away from the inbox deluge. These tools haven’t gone mainstream, but they represent a willingness to question email’s fundamentals in a way Microsoft refuses to.

These tools aren’t perfect, but they show a commitment to multi-account management and real productivity — the very areas where Outlook used to dominate.

The Lost Promise of Google Wave

Back in 2009, Google Wave attempted to reinvent communication. It was messy, half-baked, and ultimately killed off — but the idea was visionary: a single space where email, chat, documents, and collaboration converged. Fast-forward to today and communication is more fragmented than ever: email, Messenger, WhatsApp, Slack, LinkedIn, Zoom, Teams — each a silo, none a hub. Modern AI-powered email tools talk a good game, but they’re missing a trick that Wave gestured at: genuine integration across modes of communication.

Why It Matters

Microsoft is in danger of repeating the mistakes of its rivals. By forcing everything through the subscription funnel, it is alienating its most loyal power users. Those who rely on Outlook precisely because it can connect to everything are discovering that modern Outlook is less capable than the version they were using a decade ago.

Yes, Copilot can draft a neat email. But what’s the point when the real bottleneck is triaging twenty inboxes worth of noise? AI built to impress managers in a demo doesn’t solve the daily grind of people who live inside email.

What Microsoft Should Do

1. Stop hiding add-ins behind subscription tricks
   • If a user is already paying for Microsoft 365, let them run add-ins in whichever Outlook client they prefer.
2. Unify the Outlook experience
   • Right now the product line is confusing even to seasoned professionals. The “new Outlook” should not be a downgrade from the client people depend on.
3. Design for heavy users, not demos
   • Bring back serious tools for organising, filing, and managing multiple accounts. AI could be transformative here — if it’s pointed at the right problems.

Conclusion

Outlook remains powerful, but Microsoft’s current strategy is short-sighted. Forcing everyone into Office 365 to unlock features is a revenue play, not a user-centred strategy. The professionals who built their working lives around Outlook’s flexibility are being asked to compromise, and many will drift to alternatives like Spark, Canary, Mailbird, or Superhuman.

Email is not going away. But if Microsoft continues to treat heavy users as an afterthought, Outlook’s role as the backbone of professional communication may well slip away.