This is why Linux isn't mainstream.

Overall, Linux is a better OS than Windows.  I still stand by that.  But I'm not so sure it passes the "mother test"--would I install it on my mother's computer?  There are still some things that ought to be easy that aren't.  Things that Windows took care of years ago, but are still nearly impossible on Linux.  Such as automatic wireless reconnection.

If you're connected to the internet via a wireless router, and the signal temporarily goes down (as wireless signals are wont to do), Windows will automatically start looking and reconnect you as soon as it can.  Linux won't.  It'll just sit there, and it takes a dozen mouse clicks to bring your network back.

Is there a solution?  Like everything else in Linux, yes there is.  But it takes hours of research, looking through countless chatrooms of other people who had the same problem and never found a solution.  And, like many things in Linux, the solution itself has a steep learning curve and requires you to write a configuration file by hand.

As long as simple tasks like this remain so difficult, Linux will never take over from Windows.

Oh yeah, and if you had this problem, here's the solution: WiFi/WEP/WPA on Debian