When automatic “software updates” break the software

During a regular maintenance run on a MacOS X machine I asked Skype to check for software updates. It cheerfully confirmed that a new version of Skype was available for download. I allowed it to download and install the update.

Then I tried to launch Skype which to my surprise came up with “You cannot use the application “Skype” with this version of Mac OS X”.

Now, hang on.

All I did was ask the application to check if there are any updates. Updates that made it work better, closed security holes, improved stability and all that. Not updates that would stop it from working. Given that the local installation of Skype has knowledge of the OS environment and knew this was a Mac OS X 10.4.x , it shouldn’t have suggested the update¬† as there was no possible positive outcome for the end user.

To confirm this was by design and not a software glitch I resorted to the forums, where I found this:

Leaving aside the usability aspects of an application that prompts the user to take its suicidal advice, one has to wonder at the customer service lessons that can be learned here. Skype push out an update killing their own software (under conditions they don’t check), someone takes the time to report this mistake and the answer is “Won’t Fix”.

This is not just annoying, but damaging to the education of end users who are constantly hammered with¬†“always update your software!” from security people.

Guess what real people would rather have: A working but potentially vulnerable version of Skype to talk with their family abroad, or an installation that “cannot be used with your machine”?

Windows Explorer: How NOT to resolve conflicts

Let’s say you have a “drafts” folder and a “final versions” folder, and every time you publish a new version of a document you drag’n’drop the latest draft into the “final versions” folder. This used to work fine with Windows XP, you’d get a prompt saying “are you sure you want to overwrite the file?”, you’d say “sure” and it was done.


With Windows 7 someone thought it was a great idea to confuse the users as much as possible by throwing this at them:

Could this be more confusing?

I think not. I spent a good 3 minutes staring at this. Reading and re-reading it. I had to completely switch my mental context from my primary task (what I was actually doing) to deal with this riddle. I got worried I might be trying to do the wrong thing. Was I at a risk of imminent data loss? Were my backups up to date? Was this a good day for moving files? One file is newer, the other is larger… what’s going on here? There is too much information and no “just do as you’re flippin’ TOLD!” button.

I shiver at the thought of users who are presented with this. Most of them will click the red “x” to close the window and make the problem go away.

I’d love to have a chat with the usability people who conducted the study that showed more information and more choices to be a good thing for end-user interfaces. Because from the perspective of the type of users I know, this would be an unsolvable, anxiety-inducing nightmare.