Lessons from the past: Bing Chat, Copilot, and the Banana in the Machine

Microsoft's Copilot is making news, and it doesn't look so good...

-- WebProNews ran a piece titled “Microsoft 365 Copilot Faces Commercial Failure Amid Low Adoption”, citing high pricing, user frustrations, and weak performance vs rivals.

-- TechRadar and Bloomberg report that even companies that bought Copilot licenses struggle to persuade employees to switch — many prefer ChatGPT-like tools.

-- Internal doubts are growing over Microsoft’s Copilot branding strategy. Employees say users can’t tell multiple Copilot-branded tools apart.

🧩 I warned Microsoft two years ago about Bing Chat. And Copilot is proving the lesson still stands. I once called it “the banana in the machine” — after Bing Chat inexplicably pulled a line about bananas and Mount Everest from another user’s conversation into mine. Absurd, yes--and also a bit unnerving... but also a glimpse of how fragile AI privacy really was.

Back in 2023, I wrote two pieces — A Tale of Two AIs and Bing Chat Lays Another Egg. On September 8, 2023, I begged: "Microsoft should shut down Bing Chat at once on a global scale."

Bing Chat had two fatal flaws:

It leaked user conversations across sessions.
And it couldn’t get college football scores right (I mean... what else is there, right?)

Fast forward to today: Copilot is Bing Chat with better branding and the same problems. Accuracy still wobbles. Privacy still feels like an afterthought. And people still don’t trust it enough to use it.

The irony? Microsoft keeps chasing “AI transformation” while missing the basics of trust, context, and credibility. You can’t market your way around broken fundamentals.

The same six lessons from 2023 still apply:

1️⃣ Trust first. No adoption without it.

2️⃣ Accuracy matters. One bad answer can kill a reputation.

3️⃣ Don’t overpromise. The hype hangover is real.

4️⃣ Fix privacy optics. People remember.

5️⃣ Test empirically. Data beats demos.

6️⃣ Earn users. Don’t just license them.

Having AI isn’t enough--you have to make it worth trusting.

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