Wilted Rose

Suddenly my Outlook is not so Rosy, anymore. And that is the understatement of the Year.

When I’m training and we get to the subject of software tools, the discussion often gravitates towards personal organisers. Which one is the best?

Lotus Organizer has served me well since 1996 – yup! My entire life is captured and controlled in a 14 year old piece of software! Isn’t that amazing? And it still works fantastic in 2010.

But, you know what, technology moves on and people convinced me to move to the latest and greatest – Microsoft Outlook! They promised me that I would be in Nirvana!

That (moving to Outlook) was the biggest mistake I made, EVER, in my career working with IT. I have been struggling for 3 days without breaks, and I’m still only half-running in Outlook today. I expect to take another 3 or 4 days of struggles to get everything working smoothly. Even then, I have gone backwards. I seriously regret my decision to move to Outlook.

Some credentials are in order: I have been running a small ISP and doing customer support for 10 years. I know my way around computers. I don’t call support – they call me. So here is a summary of my major problems.

As background I have about 10 years of calendar entries and around 39525 messages (approximately 7+Gb uncompressed), with some 3000 contacts. Because I sometimes have to do forensic work, I need to have absolute confidence that every single message is preserved. Oh, yes, I pull mail from several POP accounts under various conditions and I travel a lot, carrying my evidence files with me – I cannot afford expensive roaming bandwidth in the hotels.

I’m not going to bother you with every single problem – trust me, there were many. But the three most severe ones are:

1. When using the Outlook import facility, it would happily report that all the messages have been imported … until you count the number of messages in each folder. Several thousand just went missing without a trace and without any error messages of any kind. Oh, and yes I tried to export from Outlook Express with very similar results. The errors are relatively consistent and seems to revolve around messages that are secured or to do with the calendars. I eventually had 200-odd messages that I just couldn’t move at all. How can I ever trust a system if it drops messages without telling me?
2. Outlook Express and other popular e-mail clients store messages in smaller files so you don’t hit the upper file size limits as easily. However, my Outlook PST file hit 4Gb (spelled death by file size) regularly. I had to resort to some serious gymnastics to move all my folders around to get PST files down to around 1Gb each. It is pathetic. I now spend my time managing the SIZE of my e-mails and not the CONTENT.
3. And then, the big one. Rules. In today’s day and age with all the spam around, I want some intelligent rules to sort my mail into the correct folders to make my life easier. While 80% of the rules work as expected, the really important ones don’t. Mail lists and/or spammers send stuff with headers that are sometimes broken or used in unusual ways and Outlook doesn’t seem to have the ability to apply a simple rule to a header record unless it is a simple [from]:[to].
4. OK this is number 4, 5, 6 … just imagine my frustration with the address books and synchronising  calendar entries and you will see the list growing rapidly but I promised to stop at 3.

In summary, going to Outlook is a downgrade, not an upgrade. Outlook is a great integrated PIM for simple users, or even corporate users whose hands have to be held, but unfortunately it has been dumbed down to reach the lowest common user profile. In the process they had to throw away (or maybe hide) the features required by an intelligent power user. I don’t know if I will continue to use it but I promised to test it for at least a week under heavy load to observe its behaviour fully.

This is not a suggestion you should use or avoid any product, it is merely a reflection of my own experience. If you want specific details I can provide you with the list of names of qualified people who I called and tried to solve my problems and gave up. May your mileage vary, please.