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Tuesday, December 16, 2025 | Digital Edition | Crossword & Sudoku

Classic failure: Microsoft digs deep and sinks

Copilot is the artificial intelligence columnist Hugh Selby is manfully trying to resist, but Microsoft has other ideas. Anyone at the ACCC reading this? Photo: Lukas Coch/AAP

“Having spent far too many hours getting nowhere, and being quite fed up, I pushed the button to renew the software. I am able to write this article which probably, maybe, means that I am re-signed to a program that I don’t want or need.” Columnist HUGH SELBY continues his tilt at Microsoft without a flicker of success. 

Sometimes a story just kinda grows and flows. When that happens the happy author just goes along for the ride.

Hugh Selby.

In this, part 2, of how Microsoft mis-interacts with its customers, I am relating what happened after their human-sounding staff told me, as you will recall, to cancel my Microsoft subscription in the Apple Store, and then come back to make the new subscription for the Microsoft 365 Family Classic (that’s without their AI) in the Microsoft store.

Back there I went. Traumatised by previous interactions with AI voices and humans on the chat box I found a 1800 phone number, usable from 10am.

After the expected sequence of pushing this and that button on my phone keypad I was speaking to a human.

I was able to quickly explain what I wanted. He was almost as quick to tell me: “We can’t fix it. You are not eligible because you purchased through a third party”.

This concept of eligible and not eligible was new to me. No one had previously mentioned it.

I explained the bleeding obvious: that I was a long-term Microsoft user, that the product I purchased via the third party (Apple) was the same product as described on the Microsoft store site. I wanted an existing product, the Classic.

To no avail, because, he said: “We can’t override that” (being the fact that the system would only let me purchase the more expensive plan with AI).

Something that should be of interest to the ACCC – and would any readers with contacts inside the ACCC please let them know – was that once my Apple-based sub expired I would become a “new” customer. As such I was not allowed to purchase Classic.

Apparently, if you’re new you gotta have, and pay for, their AI “Copilot”. Flying solo is not an option.

At that point I felt obliged to share with him that I had engaged with several of his colleagues, none of whom had raised the eligibility question.

Graciously, having been silent while he checked the previous online chat records, he said: “ I can see that previous staff said you could do it, but you can’t”.

It was at this point that I fortunately remembered a lesson taught by a much respected judge interstate. A group of us were at lunch, just a minute, maybe two from the courthouse. Court went back at 2.15. At 1.50 his Honour excused himself, saying that he needed to get back to his office to prepare for his confected rage to be on display when court resumed. He was a man with excellent judicial gravitas. I would not like to have been dressed down by him.

Politely and firmly I demanded that I be connected to someone with authority to fix the problem.

Supervisor Eric came on the line.

He and I reviewed the history. He told me that I had to go back to Apple support, speak to someone, and get them to manually sign me up to Classic.

He would send me an email and I could get back to him if this approach failed.

Eric tried to help. He was permitted by Microsoft to use his brain. This may save his job, though I don’t know for how long.

Getting through to a human in Apple ain’t easy. They too have learned that only the most nimble, persistent customers are to be rewarded. Finding their phone number takes a keen eye.

I was rewarded. The Apple system put me through to Justin. Long may this man be employed. He is in Apple tech support in the Philippines. He went far beyond the usual. Taking shared control of my Apple computer screen we explored every possibility that might allow Apple, a third-party provider, to sell me Microsoft Classic.

We came to the same conclusion. It’s impossible. He told me that I had to go back to Microsoft. I bid him farewell and good wishes.

I sat at my computer, staring at the Apple store screen that told me my subscription to Microsoft 365 was cancelled, but I could still renew it.

Having spent far too many hours getting nowhere, and being quite fed up, I pushed the button to renew it. I am able to write this article which probably, maybe, means that I am re-signed to a program that I don’t want or need.

I say “maybe” because a message from Microsoft, not Apple, has appeared in my email inbox. It invites me to renew my subscription which is about to expire. 

Before that message I replied to Eric’s email. I advised that I had given up; however, I would like the refund from Microsoft for having failed to tell me about Classic last year and driving me to renew at the increased price again this year.

Nothing ventured, nothing gained.

By the way, for those readers who like me don’t need Copilot, there are some first rate, free, word-processing programs that you can download from the web.

This article was written by a human. Next year? Um.

Former barrister Hugh Selby is a CityNews columnist, principally focused on legal affairs. His free podcasts on “Witness Essentials” and “Advocacy in court: preparation and performance” can be heard on the best known podcast sites.

Come back, Bill Gates, Microsoft needs a human like you!

Hugh Selby

Hugh Selby

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