Every single time I try to log on to the in-flight Wifi the first response screen is the infamous MasterSessionTimeout.html. Why? Probably because I keep one southwest.com tab open in my browser.
Close, but not quite: you'd have the same issue if you closed the SWA tab(s) first, because your session variable is stored in a cookie. If you delete the SWA cookies you can safely load session-aware pages without triggering the redirect to the session timeout page. It takes too many steps to manually delete cookies for a specific site, so an automated method is recommended.
I installed the Firefox extension
Remove Cookies for Site to do this and it worked well at first. Then I started getting master session timeouts even after using the Add On.

After lots of aggravation with that I finally tracked down the problem: SWA started storing the DISC cookie (and at least one more) in a bizarre (probably erroneous) format that the add-on doesn't detect.
There is a bookmarklet available that does the job completely; see
http://cybernetnews.com/cybernotes-t...-your-browser/ (look for "Remove site’s cookies" about 1/3 of the way down the page). To install, simply drag the link to your bookmarks toolbar or menu. You have to train yourself to use the bookmarklet on an open SWA tab before loading a new one, however. I tend to delete SWA cookies as soon as I'm done (however briefly) with the site.
For me, the fact that the master session timeout issue has been so bad for so long is pretty solid evidence that there are no actual users of southwest.com who have any input at all into its development. It makes for an atrocious user experience. It also makes the developers look especially idiotic when you get a master session timeout because you clicked the logout link!