The “Waiting for your exchange server“ dialog in Outlook has evoked some of the most violently negative responses I have ever seen from customers. Michael talks about this “dreaded Outlook popup” and offers the following tip:
If the server name shown in the Requesting data … dialog box is in the FQDN format, Outlook is waiting for a response from the directory service. If you see a short server name, Outlook is waiting for either the mailbox server or public folder server to respond.”
And the funny thing to me is that the dialog was originally considered a feature - instead of Outlook freezing up when it couldn't reach the server, it would give you the option to at least cancel the operation. In the case that the operation was something where canceling would be useful (perhaps you were trying to go to a public folder that couldn't be reached, but your mailbox server was reachable), it made sense, but it turned out that a lot of the time that users saw it, canceling did them absolutely no good, and the fact that Outlook taunted them with the dialog made it worse. So then we added a feature to customize the length of time before Outlook would display the dialog (at least, I think that happened after the initial implementation, after we got some feedback).
So then a feature was implemented to remove the need for the dialog entirely, aka Outlook 2003 cached mode. I've given several talks about Exchange and Outlook 2003, and they always have a slide in it with that dialog, plus an animation that draws a big red X through the dialog. It always gets applause.
When users can't get to their email, it's A Big Freaking Deal. And it is always Exchange's fault. Around these parts, we sometimes got uppity whenever Outlook informed us that our “Exchange server globalcatalog1.microsoft.com is not responding“. From time to time, we'd snort and say it's not our problem, it's the GC. Or maybe it's the network. Or perhaps the user's port just got shut off for spreading a virus or downloading porn.
Sure, it's kind of unfair to us as developers on one product when the root cause has nothing to do with our product. But the truth of the matter is that it's our customer, and we own making their end-to-end experience work (or at the very least, fail gracefully). We use the term “End-to-end messaging“; it's about ensuring that the entire experience operates as expected, stop blaming another piece of code and just make things work together better. Customers don't care whose fault it is, they just want it to work.
So, nowadays when I see that dialog, it always makes me think of end-user frustration, the improvements we've made in Outlook 2003/Exchange 2003, and where we can go next. Plus, it's really a compliment that problems with email access is such a big deal - it's nice to see that our software is that important to so many people.
 I wanted to use the word 'evisceral', but I looked it up first to verify my spelling and it doesn't exist. That's a real bummer, since I've used it many times before.
 “What's hickadoola? It's that special feeling you get when you're holding hands with your best gal!” 
 My phrasing reminded me of that episode.
 If you ask my four year old nephew “What does Quagmire say?” he says “Giggidy giggidy giggidy!”.
 If you then ask him “What else does Quagmire say?”, he says “Aawwwwwll riiight.”
 I'm fairly obsessive-compulsive. Tell me that half of analysis is anal, and I'll tell you that the other half is ysis.
 Actually I stole that one from an old friend.
 Blame the rere-download of this post in your RSS aggregator on Larry (since when is your name larry osterman? your full legal name is larryo, gosh darnit) for pointing out my typo. And Larry, I bet it's driving you nuts that  isn't referenced anywhere... muahaha