First, some background.
A few months ago, we got my grandmother an old laptop so that she could get online and check her email without bringing her old mid-tower PC up from the basement. My parents set her up with Windows XP and a few basic apps, and I set up Thunderbird to tie in to her GMail account via IMAP.
That worked fine for a month or two, until she tried to go to a website she'd seen in a flier she'd gotten in the mail. She always types URLs into the Google Search Engine, and, in this case, the top result for the URL wasn't the site itself, but a page that popped up a fancy in-page Javascript widget that looked very much like Windows XP, with a warning that a virus had been detected on her computer, and asked her if she wanted it removed.
In her panicked state, she clicked "Yes" or "Run, whichever looked to her like it might resolve the problem presented to her by the dialog she was seeing.
Symantec didn't catch it. In fact, near as I could tell, Symantec was no longer on the system; The updater program was there, but there weren't any antivirus binaries to be found. Yet the system was getting unusually flaky. I spent two days trying to clean it up with antimalware like Avast, Spybot and AVG, and none of them detected anything when I scanned.
It was time to wipe and reinstall, but I didn't have the software keys, my parents did. I booted into an Ubuntu 9.04 live CD, installed Thunderbird and configured it to connect to my grandmother's email via IMAP. As she tried the liveCD, I tweaked this or that to make the system more usable and convenient for her. I increased the system font sizes, increased the display DPI, made the mouse cursor bigger (which was tricky; Turns out one has to switch away from the default mouse theme to get control over the cursor size), made the panels 48px tall instead of their defaults, put her two most used apps in launchers (firefox and thunderbird, now), hid the pager, disabled the touch pad click and scroll functionality, and moved the GNOME menu applet to the bottom-left corner of the screen.
By this point, the system was working very well for her. I consulted with my parents, and explained to them that even with the keys for the Windows software, Ubuntu was going to be easier for me to configure and maintain for her, and she'd been using and enjoying the liveCD configuration I'd set up for her thus far. After the phone call, I imaged the laptop's hard disk (for backup purposes; It's entirely plausible that the hard drive disk image will need to be restored to the trojan-laden state at some point.), and installed Ubuntu to the hard disk itself, blowing away the Windows install that was currently on it.
So far, so good. I've even installed Pidgin, which gives her quick and easy access to family and friends, as well as a DVD player, which makes it easier for her to see movies and such.
Ubuntu isn't for a guy like me who wants to choose his window manager or frequently compile development versions of media codecs, but it's great for someone like my grandmother who gets good usage out of the usability work that's gone into GNOME. She doesn't configure it, I do. But she uses it once I've configured it, and it works well for her that way.
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