[bcrescimanno]

I'll share my own story of the Windows 3.1 -> 95 migration and MS Tech support. At the time, I was using my grandfather's old PC that had originally been a 486sx 33mhz processor with 4mb of RAM and a 200mb HDD. We upgraded the machine using an Intel "Overdrive" processor to a 486dx/2 66mhz processor with 8mb of RAM and added a Soundblaster 16 sound card and triple-speed CD ROM drive. I received a copy of Windows 95 for Christmas 1995 and proceeded to install it on the system. It worked pretty well and, a few months later, I decided I wanted to add the "MS Plus!" pack.

I was 14 years old and knew very little about PCs at the time; though, I was learning. What I definitely didn't know at the time was that the HDD in the machine that I was told was nearly 500MB was actually a 200mb drive that had been compressed with an older version of DriveSpace. The addition of Plus! upgraded the compression to DriveSpace 3 which corrupted something on the drive that caused the system to hardlock as soon as the Windows 95 UI appeared no matter what I did.

After spending 4-5 hours on the phone with a very patient tech support specialist at MS, he eventually concluded that I would need to format the drive as nothing we did in those hours worked at all. Definitely a major learning experience for me doing my first full system format and OS reinstall.

By the end of 1996, I'd be doing my first Linux installation on a slightly newer PC that I saved money from a summer job to buy. If it hadn't been for DriveSpace 3 and an MS tech support specialist who educated the hell out of me for a few hours, who knows when (or even if) I would have gone down the rabbit hole that led to my career.

[cydonian_monk]

It's difficult to explain to people today just how good Microsoft tech support was in the early-mid 1990s. We had a similarly complex issue with DOS 6.something that I don't remember the full details of, and I think I learned more about operating systems in the couple hours we were on the phone with MS than I did in the semester-long operating systems class I took in college. Some days after the call we got a stack of floppies in the mail from Microsoft with a small bug fix that helped with whatever the situation was we had encountered. Just night and day compared to most modern interactions with tech companies.

[rolenthedeep]

> Some days after the call we got a stack of floppies in the mail from Microsoft with a small bug fix

That is just so utterly inconceivable today that I didn't believe it at first. Not just being physical media, but receiving that level of attention and care.

The best you can hope for these days is a vague forum reply with some shockingly bad information from an "official Microsoft rep" who is at least 5 degrees of separation from anyone who has seen code before. Disgraceful.

[bernardv]

The most rewarding calls were those helping either very young or very old customers who just needed help getting started. I recall a grandfather calling in with his grandson, trying to figure out the new Windows machine he had just bought him. Being patient and understanding was all it took to make a difference.

[krimpenrik]

That is pretty wild, imagine that support in the current climate

[leonidasv]

This lead me to wonder if retail Windows licenses are expensive because they used to include a phone support and then, when people learned how to Google for problems, Microsoft dropped the phone support but kept the price because "customers are used to this price tag"?

I recently bought a Windows 11 machine that came with Windows 11 Home, I felt the need for some Pro features and went to check the price for an upgrade and my jaw dropped. Years of "free upgrade to Windows 10/11" lead me believe those licences were less pricey nowadays.

[mananaysiempre]

At the same time, it’s probably worth remembering the contemporary Microsoft rule of thumb that “each product-support call costs a sale”[1], that is to say, handling a single product-support call to that standard costs as much as was earned by selling the product in the first place (and the products weren’t exactly cheap—not that they’ve become cheap now).

[1] “Old New Thing” (the print one), https://books.google.com/books?id=wYrCitbs5PQC&lpg=PA1&pg=PT...

[dzdt]

Exactly. We are moving to a tine where having a person individually and attentively help you with anything is a high order luxury item.

A major change is on the horizon though. We are close to where a large language model could play the role of the support side of that call. But if it an AI on the support side, would anyone bother to learn on the customer side?