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Microsoft lost a customer today.

As I’ve written about a couple times over the last few weeks, I’ve been helping a friend of the family with his new Dell computer. His children purchased it for him along with a camera and printer so he could email, print and share photos with them.

His troubles started when the computer was first hooked up to the Internet. He was using a dial-up connection and no firewall, so before the patches were installed his machine was infected with the Sasser worm and a short time later a set of trojans.

When I got over to his place, I set up a firewall for him, removed the trojans and Sasser–which he didn’t know he had, added a password to his user account and installed the printer and camera utilities. This took a couple evenings. He was finally getting to the point where he could use the computer for what he originally intended: To have fun. Things were looking up.

You see, he’s retired. He can go play golf, or go boating, or whatever. In short, he wants to enjoy life. He wanted to try out the Internet because he thought it would be fun. Unfortunately, the virus writers, Microsoft, and Dell all worked together to convince him it wasn’t.

The clincher came last week. This time it was 100% Microsoft’s undoing. He couldn’t get to his email. He has an MSN dial up account and he was befuddled by the fact that he couldn’t dial in. When I went over to his place, I quickly realized that he was connecting to the Internet alright, but not to MSN’s services. After jumping over to IE, I could see why. Passport was failing. I tried my Hotmail account. I couldn’t sign on either. However, something strange was going on. I checked with some friends and they could all get through. I was beginning to get that sinking feeling.

When I tried connecting manually with IE using the Passport site I was getting the classic “website currently unavailable” error page. I suggested that he think of it like a busy signal and try again later. He did. But it never worked.

My inside reaction was that how unnecessarily bad this was that he could authenticate to MSN, but he couldn’t get to his email because he couldn’t authenticate with Passport. Aren’t both run by Microsoft? For a single user isn’t authenticating to one good enough? Yeah, I can appreciate the security issues, but to him here he was having to sign on to his computer, sign on to MSN, and sign on a third time to get his email–which admittedly he never realized he was doing anyway. He was getting overwhelmed.

Since then I’ve read on the Net that others have been experiencing the same problem and some have called for tech support and been told to try again later.

So he’s decided to set aside his new computer because quite simply it isn’t fun. I can understand. I told him that if he decides to try again to let me know and I’ll do what I can to help him out.

I feel bad that I couldn’t get him up and running more smoothly. At each step of the way, he seemed to run into problems. And at each step of the way I was adding more complexity to things that intuitively seem so simple.

On the plus side, I’ve seen something similar with a happier ending. I have another retired friend that I’ve been helping too. She had never used a computer before but she wanted to keep in touch with her friends. In particular, she wanted to email back and forth jokes, jokes and more jokes.

To make it work, she utilizes customized desktop icons that her friends have set up so that she can connect to the Internet as well as a memorized path of clicks and taps to get to her email. She doesn’t do anything else. She gets lost faster than IE can refresh a page on her dial up connection. I hand it to her though, she’s able to get around even though her computer usually double boots–because of a motherboard BIOS problem that I can’t find a fix for. No matter to her. It’s a hand-me-down computer so she makes do.

Yes, she’s thought about chucking the computer a couple of times. No not because of the extra rebooting. But early on she started having sign on problems with her AOL account. Seems her email address was being identified by AOL as a spam address. I can’t remember the error code she was getting, but believe me it wasn’t obvious what was going on. So she changed ISPs. A couple weeks later I got another call. This time she was running into file size problems with her email account. Eventually I set her up with Yahoo mail and all has been fine since.

Fortunately, no viruses so far. I cringe knowing that she does a lot of email and yet doesn’t have an antivirus program. But she generally never clicks on attachments, uses browser based email, and only navigates to known sites. Each time I visit her I also make sure her machine has all the recent updates. So far so good. Knock on wood.