You may not be aware, but there is intense competition between companies to create the world’s dumbest installer.  I always thought Fog Creek deserved honorable mention for writing their own installer from scratch, but I have to admit it isn’t a bad installer, that was just a waste of their time.  Sun’s Java upgrader is definitely in the running, for elevating what should be a silent little background thing into the foreground like some kind of major application that users care about.  Real’s installer is a nightmare, with 400 options in seriously deeply nested menus, most of which have the wrong default settings (“Do you want to use Real for all C++ compiles? – default Yes”).

But I have to give the award to Microsoft for their IE update to v7; in this, as in so many other things, I subtract all benefit of a doubt since they are so big and mighty and ought to know better.

I am just now applying “essential” updates to a server, and the IE update to v7 is among them.  Against my better judgment, I left the box checked, and so I am now in the throes of a horrible installer experience.  Let me count the ways this installer sucks:

• First, it is so intrusive.  If you think upgrading my browser is “essential”, so be it, but can you at least do it silently?  Do you have to make me answer a bunch of questions and watch a bunch of crap?  Who cares?  (I use Firefox anyway!)
• I cannot figure out why an installer must be a wizard.  You get a dialog box which has multiple panes, but it consists of Start, Do It, and Finish.  Why not just Do It?
• The installer has gratuitous animation.  Why?  Yes it may be pretty but try running this remotely over RDP sometime, as I am, and all that animation looks like crap.  Someone clearly had too much time on their hands.
• There is this whole Windows Genuine Advantage thing wrapped in the middle of the install.  Look, if you want to verify I have a licensed copy of Windows, great, go ahead and verify it.  And if I’m not properly licensed, say so – and then you can do whatever you want.  But don’t make me an integral part of the process of checking.  It should be silent if I’m properly licensed.
• There is even a link that says “click here to learn more about WGA notification”.  C’mon.  Who the heck wants to learn more, I want the whole thing to go away.  (Just imagine what someone like your Mom would think about this :)
• After all this, you have to agree to a user agreement for the Windows Genuine Advantage check.  A license agreement for a tool which checks to see if you have a valid license!  Look, I’ve already got Windows and IE installed, so I’ve already agreed to your EULA, now can you just please do the upgrade?
• At the end of the validation process, which is itself a meaningless wizard with Start, Do It, and Finish, when you get to the Finish there is a checkbox which says “show me some of the many benefits of using genuine software”.  This checkbox is checked by default!  If I leave it checked, it is going to launch a web browser with a bunch of propaganda.  Keep in mind, I am in the middle of upgrading my web browser.  Well actually I am in the middle of applying “essential” updates.  We’ve kind of lost the thread here, eh?
• Whew, finished with the Windows Genuine Advantage stuff, and I’m back to the browser upgrade.  Now I have to agree to another EULA for the browser.  C’mon, I’ve already got Windows and IE installed, I’ve already agreed to a EULA, do I really have to do it again?  Yes, apparently.
• Whew, got IE installed.  Naturally I have to reboot.  So be it.  (When I upgrade Firefox it happens immediately and silently and of course I don’t have to reboot.)  Silly Microsoft people.
• And as a final crescendo, once you have IE updated it doesn’t work.  No, really, on a server everything IE does is installed disabled.  There is this thing called Internet Explorer Enhanced Security Configuration which is enabled by default, and which is a euphemism for “don’t allow anything to happen”.  If you figure out how to disable this, you get a warning every time you launch IE, “Caution: Internet Explorer Enhanced Security Configuration is disabled”.  So you have to disable the warning that the warnings are disabled.  Got that?  I am not making this up.
• Oh, and as a final final crescendo, after all this you end up with something called the Language Bar enabled on your Windows taskbar.  Perhaps the Language Bar is useful, I don’t know, but I do know two things: 1) I’ve never used the Language Bar for anything, and 2) it is really hard to disable.  Seriously you have to go in like five levels deep of some Control Panel to turn it off, and then reboot to get rid of it.  I can just imagine the Product Manager for this little feature lobbying hard to have the IE upgrade turn it on by default.  Sigh.

Not only does the installer process itself take forever, but you end up so upset that you write a whiney blog post about it, wasting more of your time :)