Damn, Microsoft Outlook Really Sucks!
November 16th, 2006 by Joshua Dorkin | Filed under Commentary, Microsoft.
I cannot explain how pissed off I am at my Microsoft Outlook. I have been battling for 40 hours now to get my email working properly but leave it to Gates & Co. to screw something else up . . .
The Beginning
This problem all started when I decided that it was time to become a Phase 3 Web Success. My server has been stretched thin and there was a need to upgrade. I had been experiencing a lot of downtime over the past few months and couldn’t wait any longer. Two nights ago we set out to make the move and completed the server transfer. Understand first that I’m very happy with my new Intel Xeon processor and 15k SCSI drives. This thing is FAST! The issue is that in moving my data to the new server, I also moved all email files . . . which brings us back to:
The Problem
You would think that Outlook would recognize that it had already downloaded the email messages on this new server, but that would be too easy. Apparently, the program has a need to duplicate all old messages previously downloaded before letting me get my new emails. While this is nothing but a royal pain, it only gets worse. First, I’ve got close to 10,000 emails on the server. After going through my virus scans the total download time is counted in hours. Second, Windows XP has decided that it would make things even worse for me and has failed 4 times now prior to completion.
Back to Outlook . . . one would think that if the program downloaded 9,700 emails and crashed, it would realize where it left off and continue from there next time. That would be asking too much. I’m now receiving message 2316 2317 on my 5th try. I’m crossing my fingers in hopes that I don’t get screwed once again.
The fun part will come when I need to go back and remove the 4 duplicate messages for each original message that made it back to Outlook.
The Solution
If anyone has a solution for this email hell, please let me know. Meanwhile, I’ll be sitting here ripping my remaining hair out one by one. I’m one last screw up away from moving everything to Thunderbird.
(Note: I’ve had it with Windows machines and can’t wait to get my next computer – a PowerMac)


It’s funny but I have tried a lot of different mail programs and although Outlook is far from perfect it has the feel I’m use to. I think it is the only reason I don’t use Linux as a GUI for my own machine.
My suggetion is to connect once by IMAP move what you want over to your local machine and then delete the files from the server by IMAP. Then move over to pop.
Gary – I’ve also become used to the feel of Outlook, but this has been a royal pain. While I writing the post, Outlook actually completed the load of “new” messages. I’m finally back in action, but still think Outlook sucks because of what I had to go through!
at least hyperoffice has made some improvements with outlook for your smart phones