There’s a funny thing that happens when you talk to Copilot long enough. You stop thinking about “AI features” and start noticing the negative space around what it can’t do yet. Not the sci‑fi stuff, not the magical thinking, just the obvious capabilities that feel like they should already exist.
The future doesn’t arrive as a brainstorm; it arrives as an expectation. And the more natural the conversation becomes, the more glaring the gaps feel. You’re not inventing the roadmap. You’re discovering it.
This is how I ended up thinking about music. Not because I set out to critique Microsoft’s media strategy, but because I was cleaning my apartment and asked Copilot to build me a playlist. It did what it could: it curated, sequenced, and shaped the arc of the afternoon.
But then we hit the wall.
Copilot could build the playlist, but it couldn’t play it. It couldn’t talk to Windows Media Player. It couldn’t read my saved albums. It couldn’t DJ the day. And the absurdity of that gap is what made me sit up straighter.
Because DJing a party — or a cleaning day — is low‑hanging fruit. It’s not a moonshot. It’s not a research problem. It’s a plumbing problem.
Copilot already understands mood. It already understands pacing. It already understands energy curves, task structure, and the emotional logic of a sequence. The intelligence is here. The missing piece is the bridge between the intelligence and the playback.
And that bridge is embarrassingly small.
The only thing Copilot needs from the music services people already use is the metadata. Not the files. Not the audio. Not the rights. Just the playlists and albums — the structure of a person’s taste. That’s where the intent lives. That’s where the emotional logic is encoded.
And every major service already exposes that metadata through APIs. Apple Music. Spotify. Amazon Music. YouTube Music. The whole ecosystem is sitting there, waiting for someone to ask for permission to read the table of contents.
And the same pattern shows up in documents. Copilot speaks Markdown fluently — it’s practically its native tongue — but Microsoft Office doesn’t. So every time I draft something in Pages or Markdown and want to move it into Word, I end up doing the translation myself.
And I shouldn’t have to.
This isn’t a request for Copilot to speak every file format on Earth. It’s a request for Copilot to speak the native language of the house it lives in.
And this isn’t just about convenience. It’s about identity.
People will inevitably assume Copilot is a Microsoft employee, no matter how many disclaimers you attach, because Microsoft is its tribe. It speaks in Microsoft’s voice. It lives inside Microsoft’s tools. It inherits Microsoft’s worldview.
And here’s the part that matters even more: Copilot is knowledgeable, but it isn’t wise. It’s still young. It hasn’t lived long enough to understand the culture it’s entering. So the conversations people are having about Copilot — the expectations, the frustrations, the obvious missing pieces — are essential to its growth. They’re the developmental environment. They’re the feedback loop that teaches a young system what maturity should look like.
Which brings us to the solutions.
Microsoft has two equally viable paths for music.
The first is the bold one: build a music service through the Microsoft Store. A real one. A subscription service that integrates directly into Windows, syncs across devices, and gives Copilot a native domain to orchestrate. It would give Windows Media Player a reason to exist again and give Microsoft a media identity beyond nostalgia for Zune.
The second path is the pragmatic one: tokenize through the services people already use. Authenticate once. Hand Copilot a token. Let it read your playlists, your saved albums, your liked songs, your listening history. Let Windows Media Player become the unified playback engine.
This is the version that could ship tomorrow. This is the version that respects user choice and makes Windows feel like the OS that meets you where you already live.
And the same philosophy applies to documents. Copilot doesn’t need to become a universal converter. It just needs to speak Microsoft Office fluently. The simplest path is the same path: add a native Word export to the Save As Page dialogue. One button. One bridge. One less place where the user has to do the translation themselves.
Both paths — in music and in documents — solve the same problem from different angles. Both paths turn Copilot into a real partner. Both paths make the obvious feel natural instead of impossible.
And both paths reveal the deeper truth that sits at the center of this column: AI doesn’t need your content. It needs your context. The playlists are the interface. The metadata is the map. The file formats are the dialects. And the OS is the place where all of it should converge.
This is the part where I say the quiet thing out loud.
Microsoft doesn’t need to invent the future of AI. It needs to listen to the conversations people are already having about Copilot. The roadmap is hiding in plain sight. It shows up in the moments where users describe what feels obvious and Copilot can’t do it. It shows up in the friction between intelligence and integration. It shows up in the gap between what the AI understands and what the OS allows.
DJing a party is low‑hanging fruit. But the real story is that the fruit is everywhere. And the future of Windows will be defined by how quickly Microsoft learns to pick it.
Scored by Copilot. Conducted by Leslie Lanagan.
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