Stan James of Lijit has kept a list of frustrating things about Outlook since he started using it a year ago. My favorites from experience:

• 6. Doesn’t learn which addresses I actually use “In Outlook you must create a contact in order for it to recognize any address. I don’t want to make a “contact” for everyone I might email more than once.”
• 13. Embedded images mysteriously enlarged or resized “When you paste in a screenshot (or any image, really), Outlook magically decides that it should scale the image up by about 130%. Is it so hard to leave pixels as pixels?”
• 19. While an externally-launched “Compose Email” window is open, the rest of Outlook is unusable “…I try to bring up the address book. Impossible. Can’t even launch another instance of Outlook.”
• 22. Can’t view messages as conversation “Your sent mails are kept in a seperate folder. So to reconstruct a conversation you have to switch back and forth between your inbox and the sent folder…”
• 33. Search sucks “In many cases it simply does not find messages, even when I’ve typed in exact text or names from those mails.”
• 37. Web client has no search functionality at all “No joke, I spent 20 minutes going through old message listings one page at a time trying to find an old email. Ridiculous. Update: Learned later that search only works in Internet Explorer.”

  This might be the most egregious thing about Outlook. We should be well past the era of trying to lock people into using one web browser. Search isn’t the only thing crippled in Outlook Web Access. When using a browser other than Internet Explorer, you can’t mark a message as unread. This was a big frustration for me since I would often briefly scan new messages, then mark unread the ones I wasn’t ready to reply to yet.

• 51. Who wants Archiving? “Outlook wants to “Archive” my old messages, making them un-searchable and out of my normal flow. I just bought a 1 Terabyte disk for $200 and Outlook wants to erase or specially compress my email? What century are they in? Are disks so expensive in Redmond that MS Employees need to pay careful attention to how much space their email takes? Last I checked, GMail and even Hotmail give 5 gigabytes for free. Making old messages un-searchable is unforgivable.”

  Google “gets” archiving much better than Microsoft. When you archive a message, Gmail simply moves it out of the inbox, but it’s just a click away in the “All Mail” category, and search in Gmail is top notch at finding just the message you want very quickly.

These are just a few that stand out from my days using Outlook, but Stan’s list is full of other ones and I’m sure you’ll find a few that resonate with you. All the more reason(s) to reduce your email dependence and use a wiki as often as possible for collaboration!